Dog Walking Windsor

“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!”

Nicole S.

“Iris was pleasant to chat with. Georgia liked her and went into a calm mode with her soothing head pets. Iris handled Georgia well on the walk - maintaining control and kindness. I'm happy she'll be with Georgia sometimes.”

Tracy L.

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.

“You can tell McKenna is a big animal & dog lover. She was incredibly sweet & gentle during our meet & greet. She asked all the right questions and our pups felt instantly comfortable around her. We’re glad to establish a relationship with someone we can trust AND with someone who goes above & beyond during her visits. Thank you McKenna, we’ll be booking you again soon!”

Graham S.

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: 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: 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. Now accepting bookings for my private pet guest house, Booked and Boarded! Unlike a traditional kennel, I board only one pet family at a time, allowing your pets to enjoy a calm, low-stress stay with individualized attention. The guest house opens directly into a fully fenced backyard, giving dogs plenty of opportunities for safe outdoor play while enjoying a cozy, home-like environment. The space is also designed with (indoor) cats in mind! Booked and Boarded is a perfect space for pets (and owners!) who want a quieter, more personal boarding experience. In addition to private boarding, I offer dog walking, drop-in visits, 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 wide 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. When your pet stays with me at Booked and Boarded, you can expect plenty of communication. I send regular photos, videos, and updates throughout their chapter with me, and every boarding guest goes home with a personalized treat bag and a fun “report card” highlighting their time at Booked and Boarded. I know firsthand how stressful it can be to leave beloved pets behind when traveling. That’s why I prioritize communication, reliability, and individualized care so you can feel confident your pets are safe, comfortable, and genuinely enjoying themselves while you’re away. Whether you’re visiting the Berkshires for a weekend, heading out for a day of boating, 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! Find Booked & Boarded on Facebook! 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 dog sat a few times for my friends family when they went away on vacation and I also watch my sisters dogs all the time. I do not have a job right now so I am available whenever anyone needs me doesn’t matter the time or day even on the weekends. I only have a cat at home but I have a big backyard that I can walk your dog around in but I prefer to not have the dogs here just because I live with my grandmother.

About: ive had a couple of dogs 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. 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 keeping me company! 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, but I have an electric scooter thanks to a helpful couple I babysat for! drop off would be ideal, if youre close enough to walk to i can do that too! 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: Hello! I've had animals my whole life and love being around them. I'm available to walk dogs and give them good exercise for those that have a lot of energy. I am also available to stay overnight to take care of your house and animals. My love for animals has pushed me to study to become a veterinarian technician. I also currently work at Berkshire Veterinary Hospital so I'm comfortable bringing them to the vet in an emergency. I am also able to medicate (orally or injected) your animals. I'm also comfortable cutting nails. I have the most experience with cats and dogs but enjoy taking care of all animals whether they are furry, feathered, or scaled. I have a very calm personality so most animals trust me right away and if they don't, I'm very good at earning it. Let me earns yours and you won't regret it.

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.

“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!”

Courtney B.

About: I have years of animal care experience. Starting with watching my GSD and American Husky as a teenager. I personally own a cat and an American Staffordshire Terrier mix. I have experience with large dog breeds, medium, and small. I currently am in school asynchronously, therefore allowing me full time scheduling for pet care needs. I also have a work from home position outside of Rover that allows me to adjust my own hours. 1. As a responsible dog sitter, I prioritize the well-being and happiness of your furry friend by ensuring regular walks, playtime, and affectionate attention throughout the day. 2. Your dog's comfort and safety are my top priorities, maintaining a clean and welcoming environment while following any specific care instructions or dietary needs provided. 3. With frequent updates and photos, I aim to provide peace of mind to pet owners, reassuring them that their beloved companion is in good hands and receiving the care and attention they deserve.

“Dana is the best! Highly recommend.”

Peter W.

About: I’ve been caring for animals most of my life, starting with my own cat who is now 11 years old. I’m very experienced with daily cat care, including feeding, litter box cleaning, playtime, and understanding their behavior. In addition, I’ve helped care for my family members’ dogs, handling walks, feeding, and general care. I’m comfortable with different personalities and make sure every pet feels safe, relaxed, and well cared for. I treat every pet like my own and always follow their routine closely. I work remotely and am a full time student, so during the summer I’m fully available for any dog or cat needs!! I’m happy to help out any time from 9am-10pm :) I their usual routine as closely as possible. This includes feeding, fresh water, walks for dogs, and litter box cleaning for cats. I also spend time with them so they feel comfortable and not alone. I pay attention to each pet’s behavior and needs, and I make sure they are safe, relaxed, and well cared for while their owner is away.

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.

“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!”

Mary W.

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: 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: 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.