Personalized care for your dog or cat - Windsor
Highly-rated overnight sitters - Windsor
Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Brooke and her family were kind and loving to Millie! She hasn’t been with anyone but us and she isn’t a very easygoing pup so we were so relieved when Millie was so relaxed and happy in Brooke’s home. Brooke kept us updated and sent many adorable photos! I would absolutely book with Brooke again and will recommend her to anyone needing care for their fur children.”
“Irene has been such a great find in the Berkshires! She always gives helpful communication with each stay, and Ruby seems to love her time with Irene (and her sweet dog Goldie). Thanks for all of the care that you give to Ruby - we'll see you soon!”
“Our dog had a fabulous stay with Mahayla! Since it was our first time, Mahayla offered to come to our home to get to know our pup before caring for her the next day. They hit it off immediately and Mahayla explained her background in animal/dog behavior studies and reassured us that all would go well... and it did! Our pup had a blast trail hiking and also just relaxing at Mahayla's home. Mahayla clearly understands and loves dogs, and it was clear that she was focused on our dog's enjoyment, comfort level and care. She was also focused on our needs as the owners. Leading up to care day she was extremely responsive. On care day she sent photos and updates. A perfect stay...thanks, Mahayla!”
“Yenifer took excellent care of my dog. He was so happy with her! She made sure she communicated everyday with us during the stay, sent us pictures and updates. We are very happy with her services and would strongly recommend her. Thank you, Yenifer.”
“Nicole is very accommodating and communicative. Daisy always enjoys herself there. She loves the fenced in yard and how she is spoiled when inside. We have used Nicole several times and will continue to do so”
“Jess was great with our 2.5 year old German shepherd mix, Moose! She was super communicative and flexible, and sent photos and videos which we really appreciated. We’ll definitely book her again!”
“Karl was an amazing dog sitter! He was punctual with returning my messages, kind, caring, and provided great service for my two big Doodles! Doodles! Karl sent images which were so great to get since we love our babies like their are our dogs ❤️ I highly recommend Karl for all your dog care needs.”
“They we're great with Ranger! I received updates and pictures each day about how Ranger was doing and any antics he was up to. Lots of walks were taken and i really appreciated the help and flexibility to work with my schedule. Ranger came home happy and tired from all his excitement!”
About: I’ve been on Rover for 5 years now! I have lots of experience with animals and my education background is in biology and animal sciences I am available pretty much whenever to do drop ins or walks for your pets!! Let me know what you need and I can accommodate :) I always make sure to follow the owners instructions and communicate with them! Communication is important when taking care of someone else’s animals! I make sure to send lots of pictures as well
“Everything went swimmingly. I had to extend the stay, which happened to work out, and Heidi was very accommodating. Walter the dog was very happy during the stay and treated Heidi with affection, knowing her for only a couple of days. Cheers.”
“Patti is the absolute best! She’s very attentive and careful to give Wally the best care she can. She welcomes him like one of her own pets with lots of snuggles and walks and hanging out. I’m so glad I found her and Wally loves staying with her!”
About: I waitress, have taken care of seniors and am a certified yoga instructor. I have had cats, dogs, chicks, fish, hamsters. I currently do not own any pets. Pets to me are precious friends who are to be taken care of like children. With full attention, support and love. I work from home so I am able to provide that kind of care. I work from home (virtually) and can accommodate boarding weekdays and weekends. I keep a clean and tidy home and have a gorgeous park very close by. Pet care fits in my routine as I used to have a cat until recently. I care for pets with respect and integrity. Showing them love and care. Keeping them and the area around them clean. Accommodating to their needs by always keeping an eye for out for them.
“Amy and her family were fabulous. They made Takoda feel right at home. Takoda enjoyed making new friends, the walks and sleeping on the couch. Amy was very responsive and provided updates so we knew it was all going well. It was a wonderful experience for us and Takoda. We will definitely board Takoda with Amy again.”
“John provided Lilly with excellent care. Lilly had been traumatized by a two-day visit last year to a kennel last year. We vowed never to do that again. But her visit with John was just wonderful. Lilly will definitely be hanging out with John in the future!”
“Ericca took very good care of my dog while I was gone for three days. She sent updates and photos without me even asking, and he was in great spirits when I picked him up. Highly recommend!”
“Maritza took such wonderful care of my dog Waffles while we were out of town. Her dog Coco was a sweet little friend for him, and Maritza made sure he was spoiled the whole time. She sent lots of pics and communicated very promptly. I wouldn’t hesitate to book her again. She loves dogs and ensures they are happy puppers during their stay.”
“Amazing dog sitter, Kathleen! She really understands how to meet and great your dogs with her dogs and others. Definitely a dog whisperer no joke. Has a great safe yard, take them for walks and just overall comfortable atmosphere. Will recommend Kathleen any time 24/7 for your cool dogs.”
“We would not hesitate to use Jennifer again. She was very attentive and conscientious to our requests in caring for our senior dog, including medications. She was very loving and kind and made our dog feel very much at home. Jennifer was very communicative and responsive before and during Jessie’s stay. We appreciated knowing that all was well while we were away.”
Over 4.1 million dogs curled up for a sleepover in a sitter's home on Rover1
Cat caregivers near you - Windsor
Prices are estimates per visit for 1 cat. Pricing may vary based on your search and includes a booking fee of 11%.
“Alyson stopped in each day to feed and spend a little time with our 4 month old cat, Luna. As new cat owners, we were very apprehensive leaving someone to take care of her. Alyson was the perfect choice and we will definitely be using her again!!”
“Olivia is the best. She stopped by twice a day to feed and spend time with my cat. My cat absolutely loved her. Olivia went above and beyond by getting my mail and stopping by an extra time to change out a food bowl because my cat didn’t like that particular bowl. Cats…. 🙄 am I right? Thank you Olivia! I will definitely be contacting her in the future.”
About: I have pet/house sat multiple times over the past several years for friends and family, from small critters like guinea pigs and ferrets, cats, and even large dog breeds. I also have 2 years experience volunteering for a local shelter in socialization and vet transport, 3 years experience working for a doggy daycare and boarding facility, and I currently work part time for another local animal shelter. I am an experienced owner of dogs, cats, ferrets, chickens, guinea pigs, and gerbils. I currently work part time so I have lots of time to play with your pup, and hopefully can build savings towards a larger space to meet more people's needs! I am always looking to learn, grow, and provide better care for animals. Animal welfare is very important to me. At this point in time, due to the space I'm only able to accommodate smaller breeds that generally can get along with others. I do have a small fenced in yard, but I also have the bike trail and nearby hiking trails readily available, your dog will need to be on leash at all times when outside on walks/hikes, I do not provide "off-leash" trail experience as a safety precaution, thank you for your understanding! I am happy to provide pictures and updates of your pup whenever requested, please never be afraid to reach out!
About: I've taken care of cats since I was 15 years old and have learned that every cat has their own unique personality, comfort level, and routine. I understand how important it is for pet owners to know their cats are safe, comfortable, and cared for while they are away. Over the years, I've become skilled at recognizing cats needs, respecting their space, and creating a calm, loving environment where they feel secured and cared for.
“McKenna is an absolute gem!! She is very diligent in sending us photos and updates and I always feel like she treats our cats as if they were her own. I would highly recommend working with McKenna!”
“Trista was wonderful! She sent great pictures of all the pets. They all look so happy and well cared for. Great communication and followed all instructions. You can tell she really cares for your pets. We would highly recommend! 😊”
“Emily came through for me and Beans at the last minute! She was great about sending pictures and videos while I was away, and I came home to a happy and well taken care of kitty!”
“Paige took great care of our cats! She was very communicative and took pictures of our cats during the visits. She also left great updates during her visits and made me feel like she was keeping good tabs over the days. I look forward to having Paige watch our cats in the future!”
About: Working in various Grooming/Training facilities. I'm currently working with Bumblebee Pet Care with 5 of my own clients. My conversations with the pets are amazing. I'm currently walking dogs 2 days out of the week looking for more to work with within the week. I have an open schedule and interested. I have separate spaces available for each animal. In my care at anytime, I will use provided equipment for transportation. Your pet safety is number one.
“Iris is wonderful. Always on time and communication with her is great. She has taken such good care of our boys. They will miss her so much. Definitely will be using Iris again.”
“Hillaree was a great pet sitter for our cat while we were away on a long trip. I was nervous to leave our cat for over a week and to work with a new pet sitter, but Hillaree’s dependable communication and clear love of pets was very reassuring. She took good care of our cat as well as sent us nice updates. She could also moonlight as a professional pet photographer. We would recommend Hillaree to care for your pets!”
“Dana stayed at our house for a week while we were traveling and gave our cats exceptional care. We appreciated getting daily updates with photos and could tell that our two sociable cats loved their time with her. We're also grateful that she went the extra mile in trying to help our most shy cat feel comfortable. We highly recommend Dana for pet care!”
About: I have two male cats, Binx and Titan. Binx is 7 and Titan is 9 months! They’re the loves of our lives. I’m an experienced cat sitter and owner. I have over 15 years of experience. Please consider me for your cats next meal, litter box clean or sleepover!
“Emily was great! I scheduled last minute and she came over for a meet and greet the day before I went away. She totally understood the sometimes tricky dynamic of my pups and went above and beyond when she came over. Communication was great, and got a full report with pics after her drop-in. I would definitely hire her again…. And plan on it!”
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A perfect match for every pet
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Perfect for high energy dogs - Windsor
Prices are estimates per day for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Irene was wonderful & my greyhound, Star, liked her immediately. I needed a dog walker last minute and Irene responded to me immediately and was very professional and kind. I was so grateful for her care of my girl & highly recommend her!”
“I’m so thankful I found Tetiana. I left my 5-month puppy for the first time with her and I could not be happier. She took care of her with love and so much warmth. I received many pictures thought the day. Thank you Tetiana!!!”
“Jess took great care of my pup and sent me lots of pics and updates throughout the day! She has a sweet dog, and her dog and mine played together all day. Uva came home fed, healthy and tired! Thank you Jess!”
“She did such a great job! Nozzle came home so tired and I was a happy dog Mom bShe was able to take him at such a short notice and was a life saver for us. I would recommend her to anyone. She’s very flexible with schedules too!”
About: Hi! I’m Maura, a high school English teacher who has lived and worked in the Berkshires for 19 years. I’ve spent my entire life caring for animals of all kinds, and my goal is simple: to provide safe, personalized care so you can enjoy your time away without worrying about your pets. I offer dog walking, drop-in visits, house sitting, overnight pet care, and small farm sitting throughout the Berkshires. Whether you need someone to check on a new puppy, care for a senior pet, or manage a small farm while you’re away, I’d love to help. I have experience caring for dogs, cats, rabbits, ferrets, hamsters, gerbils, rats, large aquariums, horses, cows, goats, and pigs. In addition to caring for my own animals, I have experience managing an equine boarding facility with 19 horses on the property and am comfortable handling a variety of animal personalities, energy levels, and care needs. I am experienced with: • Puppies and kittens • Senior pets • Oral medication administration • Basic trick training and potty training • High-energy dogs • Shy or anxious animals • Horses and livestock requiring daily care routines I also offer red light therapy sessions for pets, both small and large, upon request. Coming soon: private in-home boarding! I am currently creating a private pet guest house on my property that opens directly into a fully fenced backyard. My goal is to provide a low-stress alternative to traditional kennels by boarding only one pet family at a time. This allows your pets to receive individualized attention in a quiet, secure environment without the stress of sharing space with unfamiliar animals. If this is something you’d be interested in, feel free to reach out for details. I know firsthand how stressful it can be to leave beloved pets behind when traveling. That’s why I prioritize communication, reliability, and personalized care. I provide regular photo updates and am always happy to check in while you’re away so you can feel confident that your pets are safe, comfortable, and well cared for. Whether you’re visiting the Berkshires for a weekend, heading out for a day of skiing or sightseeing, or leaving town for a longer trip, I’d love the opportunity to care for your pets as if they were my own. Please feel free to reach out with any questions about services, availability, or your pet’s specific needs. I look forward to meeting you and your animals! I’m always running errands for my pets, spending time with my pets, or I’m at the barn with my horse. Taking care of the needs of my own pets is one of my top priorities, and I can easily work your furry friend into my schedule! It’s important that we discuss your specific expectations and needs as a pet owner/parent to ensure that you get the best care! Every pet owner and pet is different and I want to tailor my approach to what your pet is used to and comfortable with.
About: I’ve been on Rover for 5 years now! I have lots of experience with animals and my education background is in biology and animal sciences I am available pretty much whenever to do drop ins or walks for your pets!! Let me know what you need and I can accommodate :) I always make sure to follow the owners instructions and communicate with them! Communication is important when taking care of someone else’s animals! I make sure to send lots of pictures as well
About: I've taken care of many dogs for family and friends. I have been house and dog sitting regularly for the same family twice a year since 2007 and through word of mouth have picked up many more clients that would happily give a reference if requested. I feed fish and small pets and I'm happy to hang out with cats, spiders, and snakes too. I work full time for a very flexible boss, so getting home to let pets out on breaks and lunch isn't an issue. Once home for the day I tend not to leave so pets will be well cared for and I'll be very present for them. I don't trust letting any pet off leash while outside unless in a fenced in yard. I'm overprotective to a fault. I have sat on a kitchen floor for 45 minutes letting a dog bark at me while getting used to having me around.
About: I had always had dogs and cat before and I got one my self his name is coco and I love being with pets specially I would like to take them to the park sometimes if it’s good outside I naturally have time most of the time don’t have nothing else To do but I keep some weekends to do other things personal for my self I have a puppy named coco he is 1 years 8 months that could give ur pet company he is very sweet and such a baby he loves playing with other dogs and I love pets and will play with them and take them out when they need to and food and water routine I am currently not working, so I am available on weekdays and weekends. My booking schedule is open so I’ll have enough time for your fur babies I don’t have a fence, but I do got a gate & a crest if needed but I have dogs, cat that can keep your dog company or cat. My fur babies are very nice and sweet with other animals so they will be good together.
“Sandi was the absolute best dog sitter! Giddy was so excited to go to doggy daycare every day and was tuckered out by the time I picked him up. He loved spending time with Copa and getting to play outside often. He even got some healthy snacks! If I’m ever back in the area I will definitely we calling Sandi! Her whole family was lovely. We’ll miss y’all!”
About: I bring a unique level of structure, energy, and reliability to pet care through my experience as a college coach. My daily work revolves around building routines, paying attention to small details, and making sure individuals are supported and performing at their best — and I carry that same approach into caring for dogs. I am highly dependable and organized, so you can trust that your dog’s schedule, feeding routine, and exercise needs will be handled consistently. I also bring an active lifestyle, which is great for dogs that need engaging walks, playtime, and attention. What sets me apart is the level of care and awareness I provide. I pay close attention to behavior, energy levels, and any changes, and I prioritize clear communication so you always feel confident while you are away. My goal is to make sure your dog feels comfortable, safe, and well cared for at all times My schedule is currently wide open following the end of the swim season, which gives me plenty of flexibility for walks, drop-ins, and overnight care throughout the week and weekends. I understand how important it is to trust someone with your dog. I create a safe, comfortable environment where your pet feels secure and cared for at all times. I pay close attention to their needs, keep a watchful eye during walks, and always make sure you are updated so you can relax knowing they are in good hands.
About: My name is Jess! Thank you for stopping by! ☺️ I’m 30 and work from home in Adams, MA. I have a fairly flexible schedule and am a classic Berkshire native. I have been a pet owner and lover my entire life! My boyfriend and I currently have two cats, Binx & Titan. Who are the loves of our lives. My family has always been pet lovers! We’ve recently lost our two havanese pups. We were pervious owners of a chocolate lab and a poodle mix. I’ve spent my life around different breads of dogs, big and small. As well as lots of cats! I will care for your pets just as you would and am happy to provide in home care in their own space to provide the best comfort. I am confident in handling all types of breds and needs of pets. I’ve been an experienced dog sitter for over 15 years! I started doing this when I was a teenager and never stopped. I love caring for animals. Please consider me for your pets next walk, meal, or sleepover! I currently work from home full time! I prefer to chat to see if the conditions work for both myself and the pets! Always open to questions/concerns/inquiries! My message box is always open. I prefer to care for pets just as you would! I love to understand their current routine and try to keep things as normal as possible for them to prevent anxieties.
About: I’ve had and taken care of pets since I was a young child. I have 20 years experience dog sitting for one or multiple dogs. I am currently out of work so my schedule is very flexible. I am home most of the time and have reliable transportation for services. The animals needs are extremely important to me. I make sure they are well fed, entertained, and exercised. Hydration and rest are also a must!
About: I am a working professional with 12+ years in both personal and professional animal care. I love animals so am pet sitting as a side job to my remote day job in medical writing. Personally, I have cared for my own and others’ dogs, cats, rodents, and reptiles. I currently have 2 cats named Callie and Disco. Professionally, I have cared for horses, small & large reptiles, small exotic mammals, primates, and rodents in zoo, farm, and lab environments. I am comfortable with any size of dog or cat and have experience providing medications and injections to a variety of animals. I can do drop ins, walks, and overnight sitting, and am most available in the early morning and late evenings on weekdays and most weekends, as well as weekdays during lunch break. I am located in Stamford, VT and can travel within about a half hour radius of that. I also have experience jogging with more active dogs, including very large ones, and am happy to do that as well if that’s something your dog enjoys. I look forward to meeting and caring for your dog, cat, or other pet! My schedule varies but is usually flexible. I just need some advance notice to plan ahead for your pet. A week or more is ideal. I will always keep your pet safe in my home or yours. Please be aware I have 2 cats who will be in my home if the service you are requesting is at my home.
“Moxie had a wonderful time with John. She came home tuckered out and by the pictures looked like she had a great time. He was very professional and personable, we would highly recommend John.”
More than 1.6 million pets enjoyed cuddles and care from sitters on Rover1
Adventure-ready dog walkers - Windsor
Prices are estimates per walk for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Olivia is great with our new puppy! She is helping with training efforts and tiring her out during the day! I can trust that my puppy is in good hands while I’m not home!”
“Danielle is the best dogwalker I've ever had. She's very attentive and knows each dogs special needs. They love her and go crazy when they hear her car in the driveway. I couldn't be happier!”
“McKenna came to walk my pup today and I came home to a happy and tired dog. McKenna is a very reliable, punctual, and caring dog sitter. She is extremely trustworthy and I recommend her wholeheartedly. My dog loves her!”
About: I acknowledge that routine is important with pets and therefore will mold my style to fit your pets norm. (This includes your rules for your pet, anything you are training them to do, and any medication). Before taking care of your pet I make sure I fully understand their daily routine to make sure their schedule isn’t thrown off. I have experience administrating medicine to pets. I also have experience giving baths to pets as long as their grooming supplies are supplied. Also I have taken care of pets for around 3 years and am very flexible as I want to make it as easier on you as possible. I am a teacher so I have all day to spend with your pup during summer months. Also during the school year, I get off in the late afternoon on Weekdays so I can be there to take care of your pup by early evening. I respect my clients space and I am also happy to take care of any additional things around the house (watering plants, bringing in mail, etc.) if asked.
About: Working in various Grooming/Training facilities. I'm currently working with Bumblebee Pet Care with 5 of my own clients. My conversations with the pets are amazing. I'm currently walking dogs 2 days out of the week looking for more to work with within the week. I have an open schedule and interested. I have separate spaces available for each animal. In my care at anytime, I will use provided equipment for transportation. Your pet safety is number one.
About: I have been taking care of animals since I lived at home when I was younger with my parents I was very responsible I love talking to my animals I love taking time with them, making sure that they feel loved And that they felt like they were part of the family! I do work full-time, but during the day, I am able to have a flexible schedule and care to animals. I have more availability during the weekends. I care for pets in my home I make sure that my home is pet proof specially, since I have a dog of my own I make sure that everything that would be unsafe to my dog is put away if areas need to be gated off and make sure that they’re gated off and they make sure that she has all the food that she needs healthy foods and water to drink. If I was caring for a pet and someone else’s home, I would follow instructions that they leave for me and I would also make sure that their pet was comfortable and safe
About: I grew up with dogs my whole life. My parents also run a dog sitting business on cape cod and I help out there when I can! I am also fully insured! I’m a current second grade teacher, so I’m completely free on the weekends and the summer months, as well as school vacations to take care of your furry friends! I will love your dog like my own! I’m a diligent, reliable and clean person that will leave your home and dog happier than I found it. I am also fully insured!
About: Hi! I’m Maura, a high school English teacher who has lived and worked in the Berkshires for 19 years. I’ve spent my entire life caring for animals of all kinds, and my goal is simple: to provide safe, personalized care so you can enjoy your time away without worrying about your pets. I offer dog walking, drop-in visits, house sitting, overnight pet care, and small farm sitting throughout the Berkshires. Whether you need someone to check on a new puppy, care for a senior pet, or manage a small farm while you’re away, I’d love to help. I have experience caring for dogs, cats, rabbits, ferrets, hamsters, gerbils, rats, large aquariums, horses, cows, goats, and pigs. In addition to caring for my own animals, I have experience managing an equine boarding facility with 19 horses on the property and am comfortable handling a variety of animal personalities, energy levels, and care needs. I am experienced with: • Puppies and kittens • Senior pets • Oral medication administration • Basic trick training and potty training • High-energy dogs • Shy or anxious animals • Horses and livestock requiring daily care routines I also offer red light therapy sessions for pets, both small and large, upon request. Coming soon: private in-home boarding! I am currently creating a private pet guest house on my property that opens directly into a fully fenced backyard. My goal is to provide a low-stress alternative to traditional kennels by boarding only one pet family at a time. This allows your pets to receive individualized attention in a quiet, secure environment without the stress of sharing space with unfamiliar animals. If this is something you’d be interested in, feel free to reach out for details. I know firsthand how stressful it can be to leave beloved pets behind when traveling. That’s why I prioritize communication, reliability, and personalized care. I provide regular photo updates and am always happy to check in while you’re away so you can feel confident that your pets are safe, comfortable, and well cared for. Whether you’re visiting the Berkshires for a weekend, heading out for a day of skiing or sightseeing, or leaving town for a longer trip, I’d love the opportunity to care for your pets as if they were my own. Please feel free to reach out with any questions about services, availability, or your pet’s specific needs. I look forward to meeting you and your animals! I’m always running errands for my pets, spending time with my pets, or I’m at the barn with my horse. Taking care of the needs of my own pets is one of my top priorities, and I can easily work your furry friend into my schedule! It’s important that we discuss your specific expectations and needs as a pet owner/parent to ensure that you get the best care! Every pet owner and pet is different and I want to tailor my approach to what your pet is used to and comfortable with.
About: I've taken care of animals all shapes and sizes since I can remember. Growing up my only job was to make sure my fur babies were fed and loved unconditionally. I would go to a friend of the family and help her with her pit bull and (several) greyhounds. I've worked at kennels from a young age and have had my own share of birds, mice, fish, hamsters, Guinea pigs, and chinchillas as well as dogs and cats. The home has only been without pets for around 7 months now and I would love to dedicate some of my time to people who need genuine love and care for their fur babies! I do not have a job, I am around all of the time! I can be there any time day or night! You name it. I do not have a fenced in yard, however all of the neighborhood doggies are very very friendly. I have a decent sized yard and live next to multiple fields and grassy areas.
About: ive had a couple of dog growing up in my childhood a sweet old black lab and a super crazy dingo.. in my free time after school and during summer i used to walk them, no amount of walking could satisfy my dingo.. id have her pull my bike to get all her energy out since we didnt have any closed in areas she could run off in.. ( i dont do this anymore! i realize its not very safe! she absolutely loved it for sure though) i love pups big and small old and energetic theyre all very unique and id love some new friends to get me out of the house. id ask you beforehand of course if youd be okay with them swimming, theres a pond i can bring them to after walking to cool off at. our backyard is fenced! i have two cats, so id like to know how your dog reacts around small creatures, if they cant be in contact i can always but them into a room while the dog is over. most likely theyd be outside! lots of shade and id keep em well hydrated and happy :3 i currently have been on a job hunt since what feels like forever, my schedule is very. very open.. since i dont have a car, drop off would be ideal, if your close enough to walk to i can do that too! weekends are the only time id be able to pick up your pooch my cats get their waters filled and cleaned almost daily, lots of love of course and are very spoiled. i dont have any dogs at the moment, so of course id love to chat about what youd expect and need for your lovely pup! im good with communication and friendly, special needs id be extra attentive to. im very good at remembering small things, though id still write em down incase!
About: Pet/animal care is part of my soul and my heart. From puppies to seniors I shower them with love, patience and dignity. I love it! I have the time and the space for your sweet fur babies on the weekends and after work. If I can help you, please let me! I will always adapt to the needs of each animal. If I can accommodate any needs, cautions or desires, It will be my pleasure! :)
“Hillaree was wonderful! She was quick to respond, easy to talk to and the dogs liked her (we have 3 so we have a pack to please). She walked our two larger young dogs like a pro and they enjoyed her company. Hillaree has an excellent understanding of dogs, she is conscientious and she is clearly a hard working lady. We will be booking again!”
About: I’ve taken care of dog of many sizes and health conditions, I have had a cat for 9ish years and have cared for friend and families dogs for years. I am a student, I am relatively free but lots of work to do! I like to go on walks already! I am able to be flexible. I know how to feed animals and care for them, can follow special instructions as I know they are important. As much as I would love to care for your fur baby at my home, I cannot.
About: I’ve always loved animals. I volunteered at a dog groomers bathing, walking, etc. when I wasn’t old enough to get a job yet just so I could be around the animals. I grew up with a cocker spaniel and rescued my own dog as an adult as soon as I lived somewhere that would allow it. I’ve been around all different types and sizes of dogs and cats and love them all. I am currently working per diem and looking for a remote job so my schedule is very flexible. I am a morning person but don’t mind being up late either so all times are doable. I have a lot of common sense and spacial awareness so I am able to make good decision and be aware of anything that could be harmful to your babies.
About: My experience in pet care began during my childhood on my grandparents’ farm, where I was surrounded by a wide variety of animals every day. From an early age, I learned the importance of responsibility, compassion, and attentive care. I gained hands-on experience feeding, grooming, and nurturing animals of all kinds—including dogs, cats, livestock, and small animals—each with their own unique needs and personalities. More than just daily routines, I developed strong, loving bonds with the animals I cared for, treating them as family. That foundation shaped my deep understanding of animal behavior and my commitment to providing patient, personalized, and reliable care for every pet I work with. I bring a deep love and understanding of dogs of all ages, sizes, and personalities. From playful pups to sweet seniors, I tailor each walk to fit their needs. I prioritize safety, communication, and fun—always engaging with your dog and even teaching basic cues like sit, stay, and wait during our adventures. I’m passionate about nature and I believe dogs thrive when they can safely explore their environment —sniffing the breeze, feeling the grass under their paws, and soaking up the world around them. I’m dependable, energetic, and treat every dog like my own. Whether it’s a gentle stroll or a playful outing, your pup will be in great hands and have a tail-wagging good time! Dog walking fits perfectly into my current routine. I’m a part-time healthcare worker with a consistent schedule, working from 8 a.m. to 1 p.m. on Monday, Tuesday, Thursday, and Friday. Outside of those hours, I have a flexible schedule and plenty of availability and plenty of time to dedicate to your pup. I truly enjoy incorporating walks into my day—they keep me active, bring me joy, and let me connect with more wonderful dogs. Your dog will receive dependable, loving care from someone who’s already made this a part of daily life. Safety, trust, and a positive environment are at the heart of every walk I take. I prioritize clean, open, and dog-friendly spaces—like the Rail-Trail, local parks, and secure walking paths—where pups can enjoy fresh air and nature safely. I always use leash control, stay highly observant of their behavior, and make sure every walk is calm, comfortable, and secure. Whether we’re exploring a quiet trail or playing at a safe dog park, your dog’s well-being is my top priority. You can trust that your pup is in caring, capable, and experienced hands every step of the way.
About: I’ve dog sat on numerous occasions for friends and family with dogs. I’ve sat bigger dogs, smaller dogs. Older and younger. I love dogs and their kisses and loves. I love playing with them and help getting exercise or just cuddles in. I do work but I can be flexible to help care for needs of the pets. I will always check in and keep open communication to ease anyone’s mind on their pets check ins. I will always make sure the fur baby feels comfortable in their home, as I will just be a guest in it. I will give them the care and love they need though.
About: My name is Jess! Thank you for stopping by! ☺️ I’m 30 and work from home in Adams, MA. I have a fairly flexible schedule and am a classic Berkshire native. I have been a pet owner and lover my entire life! My boyfriend and I currently have two cats, Binx & Titan. Who are the loves of our lives. My family has always been pet lovers! We’ve recently lost our two havanese pups. We were pervious owners of a chocolate lab and a poodle mix. I’ve spent my life around different breads of dogs, big and small. As well as lots of cats! I will care for your pets just as you would and am happy to provide in home care in their own space to provide the best comfort. I am confident in handling all types of breds and needs of pets. I’ve been an experienced dog sitter for over 15 years! I started doing this when I was a teenager and never stopped. I love caring for animals. Please consider me for your pets next walk, meal, or sleepover! I currently work from home full time! I prefer to chat to see if the conditions work for both myself and the pets! Always open to questions/concerns/inquiries! My message box is always open. I prefer to care for pets just as you would! I love to understand their current routine and try to keep things as normal as possible for them to prevent anxieties.
About: I have owned a dog since I was 3 years old, I grew up with her and she is the greatest blessing! I truly believe dogs have many skills and a way of communicating that no one else can while showing you the most live and affection! I am available anytime Monday-Friday and can be scheduled for availability on weekends if needed! I am very flexible and willing to work with you and your needs! I show any puppy love and compassion. I take time to allow them to get comfortable and get to know me. I do not force dogs to get along with someone they do not like
Over 980,000 dogs traded couch time for play time with Doggy Day Care on Rover1
Large dog specialists near you - Windsor
Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Irene has been such a great find in the Berkshires! She always gives helpful communication with each stay, and Ruby seems to love her time with Irene (and her sweet dog Goldie). Thanks for all of the care that you give to Ruby - we'll see you soon!”
“Our dog had a fabulous stay with Mahayla! Since it was our first time, Mahayla offered to come to our home to get to know our pup before caring for her the next day. They hit it off immediately and Mahayla explained her background in animal/dog behavior studies and reassured us that all would go well... and it did! Our pup had a blast trail hiking and also just relaxing at Mahayla's home. Mahayla clearly understands and loves dogs, and it was clear that she was focused on our dog's enjoyment, comfort level and care. She was also focused on our needs as the owners. Leading up to care day she was extremely responsive. On care day she sent photos and updates. A perfect stay...thanks, Mahayla!”
“Nicole is very accommodating and communicative. Daisy always enjoys herself there. She loves the fenced in yard and how she is spoiled when inside. We have used Nicole several times and will continue to do so”
“Karl was an amazing dog sitter! He was punctual with returning my messages, kind, caring, and provided great service for my two big Doodles! Doodles! Karl sent images which were so great to get since we love our babies like their are our dogs ❤️ I highly recommend Karl for all your dog care needs.”
“They we're great with Ranger! I received updates and pictures each day about how Ranger was doing and any antics he was up to. Lots of walks were taken and i really appreciated the help and flexibility to work with my schedule. Ranger came home happy and tired from all his excitement!”
“Everything went swimmingly. I had to extend the stay, which happened to work out, and Heidi was very accommodating. Walter the dog was very happy during the stay and treated Heidi with affection, knowing her for only a couple of days. Cheers.”
“Patti is the absolute best! She’s very attentive and careful to give Wally the best care she can. She welcomes him like one of her own pets with lots of snuggles and walks and hanging out. I’m so glad I found her and Wally loves staying with her!”
About: I waitress, have taken care of seniors and am a certified yoga instructor. I have had cats, dogs, chicks, fish, hamsters. I currently do not own any pets. Pets to me are precious friends who are to be taken care of like children. With full attention, support and love. I work from home so I am able to provide that kind of care. I work from home (virtually) and can accommodate boarding weekdays and weekends. I keep a clean and tidy home and have a gorgeous park very close by. Pet care fits in my routine as I used to have a cat until recently. I care for pets with respect and integrity. Showing them love and care. Keeping them and the area around them clean. Accommodating to their needs by always keeping an eye for out for them.
“Amy and her family were fabulous. They made Takoda feel right at home. Takoda enjoyed making new friends, the walks and sleeping on the couch. Amy was very responsive and provided updates so we knew it was all going well. It was a wonderful experience for us and Takoda. We will definitely board Takoda with Amy again.”
“John provided Lilly with excellent care. Lilly had been traumatized by a two-day visit last year to a kennel last year. We vowed never to do that again. But her visit with John was just wonderful. Lilly will definitely be hanging out with John in the future!”
“Ericca took very good care of my dog while I was gone for three days. She sent updates and photos without me even asking, and he was in great spirits when I picked him up. Highly recommend!”
“Amazing dog sitter, Kathleen! She really understands how to meet and great your dogs with her dogs and others. Definitely a dog whisperer no joke. Has a great safe yard, take them for walks and just overall comfortable atmosphere. Will recommend Kathleen any time 24/7 for your cool dogs.”
“Kate is sooo wonderful! It was my first time looking for a sitter and i was worried because I never left my dog with someone that’s not my family members or friends but my Bella took to her right away and gets so excited to see her. Kate is very responsive to texts and keeps me posted with photos I feel so much at ease knowing that my pup is well looked after. Thank you Kate for taking such a good care of my dog while I was away 🙏🏻”
“I felt very comfortable leaving my pup with Mary and Todd. They have a lovely home and included my dog in all of their activities: walking, running, and much more. They also kept me up to date with pics and anecdotes. I would highly recommend Mary and Todd to anyone!”
“Robin and John always take such amazing care of my little Fred. Her dogs are so gentle with him and he always has plenty of outside time to run wild. I wouldn’t trust anyone else to watch him!!”
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1Global data from Rover (November 2025)