Personalized care for your dog or cat - Winchester
Highly-rated overnight sitters - Winchester
Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Our dog Chloe had an amazing stay with Yesika and we hope she is available in the future! She is loving and professional, and Chloe got plenty of exercise, playtime, and cuddles during her stay. Highly recommend.”
“Paul is just the best. Very communicative and makes pick up & drop off super easy. Love the frequent picture updates of our dog’s staycations. Gives us peace of mind that Thomas is getting constant care and attention when we’re out of town. Thankful to have found Paul on Rover and I know Thomas is, too! Highly recommend.”
“Betsy and her family created a welcoming environment that made it easy for our nervous dog to adjust. Betsy gave him all the care and attention he needed and was super responsive through our vacation. We will try to book again before we move.”
“Guillermo is the best. He took very good care of our dog during our 2 weeks trip. He is gentle and patient with our anxious dog. He also gives us photos and updates everyday. Would definitely recommend him to people for pet sit next time!”
“Maddy was so wonderful with my dog Jester!! We got tons of pictures and videos and you could tell how happy Jester was staying there. I was assured the whole time that my dog was well taken care of. We will use her again!”
“It's always hard to leave your dog behind while on vacation but I instantly felt as ease as soon as I dropped my baby boi off. He had an amazing time and the daily photos and updates were much appreciated. And because he was so well taken care of, I could fully enjoy my trip. I highly recommend.”
“I had an absolutely wonderful experience with Linda! From the moment I met, it was clear how caring, reliable, and attentive she is. My furry baby was happy, well-exercised, and clearly comfortable the entire time I was away. Linda provided just enough regular updates and photos showing how cared for my baby was. It’s such a relief to know my baby was treated like family. I wouldn’t hesitate to book her again and highly recommend Linda to anyone looking for a trustworthy and loving sitter.”
“Luci and her family were so great with our Charlie! Pictures and updates every day made us very comfortable with leaving him behind! They were awesome. Highly recommend!!”
“Zelun was so good with our dog. We will definitely be using zelun in the future. He sent lots of photos and had great communication. He also brought Iggy on many adventures each day like the park and nice walks!”
“Ann and her husband took incredible care of our dog. She sent updates and photos regularly while we were away. She was also very accommodating with the drop off and pick up schedule, and was able to accommodate a last minute schedule change. It’s clear that Ann and her husband are dog lovers and go and beyond in their care. We will definitely use them again!”
“Janette and her family were so welcoming and loving with my dog, Ridley. We got lots of updates and photos of her enjoying her stay, and felt completely at ease leaving her in their care.”
“Man & Zhen took great care of Wadsworth! They took him on lots of walks and sent a ton of photos. I could tell they treated him like part of the family :-) I would absolutely book with them again!!”
“Belinda was wonderful with our furbaby and sent us an update each day. She was very accessible by text and easy to communicate with. Our dog got along well with her dog, Sloane, who is a sweetie. Also, she has the perfect fenced in yard for the dogs to play! We will certainly work with Belinda again!”
“Hannah is wonderful! Our dog, Chente, loves staying with her. She is responsive, professional, and always send photos of our dog on their walks or in her house. Will definitely book again.”
“Frodo had a great stay- enjoyed playing with the hosts' dogs, I got great pictures and video updates, easy to communicate with. Would absolutely use again.”
“Yang was absolutely amazing watching Tormund. She went above and beyond what I expected from my first time using Rover. She's going to be the first person I go to for any future dog sitting needs.”
“Katheryn was absolutely amazing with her care of our two greyhounds. She was very communicative and attentive to their needs. I highly recommend her and her husband and will trust her with our pets any time! Thank you!”
Over 4.1 million dogs curled up for a sleepover in a sitter's home on Rover1
Cat caregivers near you - Winchester
Prices are estimates per visit for 1 cat. Pricing may vary based on your search and includes a booking fee of 11%.
“James was amazing!! Super communicative and gave tons of details and photos after each visit. You can tell he genuinely loves animals. He was also kind enough to water my plants and even stayed longer one day when my cat had thrown up. Highly recommend and would 100% book again!”
“Caitlin was great and took excellent care of my two cats. She made sure they had plenty of cuddles as well as play time to burn off all their energy. They were definitely well cared for.”
“Sanela was great and I would definitely use her in the future to care for my 2 cats. She is caring and treated the cats as her own. She took lots of pictures and was easy to communicate with. My car Leo requires insulin injections every 12 hours and I was so happy to find someone that could provide that level of care.”
“I couldn’t be happier with the care my cat received! Noila kept me updated with frequent messages and adorable photos, which made being away so much easier. My cat was in great hands and getting lots of attention. I’m very grateful and would absolutely book her again. Thank you Noila!”
“Lisa took great care of Cedric while we were away for the holidays! She provided lots of updates and photos and we felt like Cedric was in good hands the whole time we were away. We would definitely book Lisa again in the future”
“Angela is the best! She managed to coax our shy cat out of his shell during her visits and sent great pictures to document each check-in. We can't recommend her highly enough!”
“I came home to pretty happy cats (except for the inevitable shunning because I left in the first place), and that's always what I'm hoping for! Elisangela sent me good updates on her daily drop in visits.”
“Shawn dropped in to take care of our two cats multiple days during our long vacation. It was a huge relief knowing they were in good hands and getting photos each day. She followed our detailed feeding instructions that involved wet food with medication mixed in, and measuring out dry food on a scale. She also gave us detailed updates on their behavior and it was clear she really cared about their comfort and mood while we were gone. Thank you Shawn, would definitely book again!”
“Yesika was able to check on our cat very last minute, she showed up on time, communicated well and took care of our kitty while we were away. I highly recommend her and will use her services in the future.”
“Natalie is incredible! She not only spends time with my kitties but makes sure they are healthy and happy! She is so helpful with my Socket’s medical needs and makes me feel comfortable knowing they are well cared for while I’m away. Thank you again for another wonderful visit!”
“Meg was a fantastic with our two older cats who require a little extra in their age, and they both warmed up to her immediately. She easily took on daily meds for one who can be difficult and gave lots of attention overall to both cats. She was very responsive and sent great updates so I didn't worry at all. She even swept up litter and did kitty dishes before she left! Thank you, Meg!”
“Caroline was very friendly. She did a great job taking care of our cat Leo while we were away. Would highly recommend and rebook with her again the next time we go away! Thank you Caroline”
“I had a great experience. They took really good care of Tiger and I felt comfortable leaving her. She was well looked after the whole time and I did not have to worry. Everything went smoothly and was handled the way I hoped. I would recommend them, and I will definitely use the service again whenever I need a cat sitter.”
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A perfect match for every pet
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Perfect for high energy dogs - Winchester
Prices are estimates per day for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Fantastic puppy sitter!! Jasper loves going to play at Carol's and comes home exhausted. I love knowing he's well looked after, happy, and safe. Great communication and pictures. Thank you so much!!”
“We appreciated Paul’s help with a last minute request to watch our pup for two days over MLK weekend. He was patient with Gracie, as she was getting used to being in a new person’s house.”
“Loves my dogs as much as I do, always pays attention to the little details like medications and making sure I get all of their toys back, and super flexible about scheduling even with my weird schedule.”
“I cannot recommend Marie enough! Nova fell in love with her instantly and warmed up to her so quickly. Marie has such great energy, and you can tell she’s a genuinely kind and caring person. It’s clear she took excellent care of Nova, who had the best time with her. We’ll definitely be booking with Marie again and again!”
“Cardinal had so much fun at his small-dog play date!! I appreciated that Betsy took time for a thoughtful meet and greet so that I was sure he would feel comfortable! I was very happy that he could enjoy time outside of his crate with other dogs in a warm and caring environment! Will definitely book again!!”
“Belinda was amazing with Juno and helped out while I was at work for a work trip! Juno had a great time and it was amazing knowing Juno was in great care! Thank you so much!”
“Thank you Hannah for taking such good care of Milly!! We gave Hannah detailed notes for Milly because she is a reactive dog and we’ve been working with a behaviorist to try to calm her anxieties and fears. She followed them and kept her happy and healthy!”
“Elizabeth and Neil are absolutely wonderful! They treat my pup as their own and are the nicest and most accommodating people. I trust them fully with my pup!”
“Ben was great with Pepper! He was able to take care of her on short notice and was very flexible when I needed to change the pickup time from noon to 5 p.m. Pepper came back happy and it definitely looked like she had a great time with him. Really appreciate Ben’s help and flexibility!”
“We so appreciate Kayla! Our dog was a little shy and concerned about being left behind, but Kayla took care to introduce him one by one to the other dogs, and soon he made a bestie! We will definitely let him stay with Kayla next time we need a doggy daycare.”
“Cheuck was so great with my dog Annie! I left my dog with Cheuck during the day while I was at work. He shared pictures and kept me updated regularly! I highly recommend Cheuck.”
“she is very kind and compassionate. Great person. She is taking care of my dog with hip problems. I can leave my dog with no hesitations. Thank you Sue.”
“Was on a trip to MA for the weekend. Very happy that I found Marcia to take care of my dog for the day while I was out. She provided a lot of pictures and updates without me having to ask. She went above and beyond! She took my dog out for multiple walks as well as letting my dog outside in her fenced in backyard all day. If I am back in MA again, definitely will be reaching out!”
“Our dog has a great time with Lee! We were looking for a slower paced daycare option as she gets older (daycare facilities tend to be too overwhelming for her), so Lee and his dog Sharif have been a great alternative for keeping her entertained, but not completely overwhelmed / exhausted.”
“Elizabeth and her kids took amazing care of Bean! Elizabeth was incredibly accommodating in setting up a space for Bean in her home and truly went above and beyond. She also sent various updates and photos throughout Bean's stay with her. Would definitely recommend!”
“Finn has been loving his days with Likun! Her dog loves to run and play as well, so it’s a great match! Finn gets outside time, walks, and naps during his stay and always comes home tired and happy. Thank you Likun!!”
“My dog had a wonderful stay with Xiuping and her family. They are so kind and friendly. Very responsive and trustworthy as well. I got many cute pics and felt my dog was given a lot of attention and well cared for. I would definitely rebook next time.”
“Vista had so much fun during daycare with Junho and Boki! Junho was very communicative of how Vista was doing, making sure she had everything she needed to enjoy her days, from her food, to play and outside time. It is clear that he truly loves dogs and I would recommend him to anyone looking for someone with a kind heart to care for their pet.”
More than 1.6 million pets enjoyed cuddles and care from sitters on Rover1
Adventure-ready dog walkers - Winchester
Prices are estimates per walk for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“James was seriously the best!! So sweet and patient with Lilly, you can tell he really cares. We’ve worked with other people on Rover before, but no one like him. He always sent the nicest updates and the cutest pics after each walk, which we really appreciated. Felt so good knowing our baby was in such good hands. Thank you, James!! 💛🐾”
“If you are looking for someone who will treat your dog like family, then book Felicia! She is amazing! She took the time to meet our dog prior to walking him, and made sure she understood everything about him prior to walking him. She is also very communicative and takes a lot of pictures during their walks. I’m so glad we met her, and now our dog has a new friend too!”
“Alexa is fantastic! We hired her for daily walks, and she shows up on time, walks further than she has to, and provides great feedback through the app. Our dog loves her and she’s great with communication. Would definitely recommend!”
“Angela has been a lifesaver. She was quick to respond when we needed a last minute, recurring walker and worked around our hectic schedule for a meet and greet. Our two labs absolutely love her and look forward to their morning walks. She’s communicative and considerate and I also look forward to seeing her in the mornings as she has a great personality! She’s a pleasure to work with and we are lucky to have found her. Highly recommend!”
“Ugur provides top-notch service walking our dog. He is kind and friendly. We hired him to walk our 7-month old puppy and she loves him. Although we hired him to walk our dog, when he came for a meet and greet, our cat warmed up to him immediately and let her pet him, which she normally doesn't do for most people. We highly recommend his services!”
“Liz is an amazing caregiver for our little pup! She gives attention to his puppy experience and communicates with me about the details. She really cares and is so very capable with pups!”
“Hannah is definitely the best walker I have ever met. She is so responsive and sweet, always having a safe and happy walking journey with my doggy. I will always go back to her.”
“Kristen is an amazing dog walker for our two small pups! She was flexible and willing to start last minute when our previous walker was no longer available. She always provided a photo for me from her visit - it was a nice touch to see my happy pups during my work day : ). She also gave lots of extra snuggles and pets and checked water dishes for me. Overall, Kristen is a fantastic dog walker that I would 100% recommend!!”
About: Dogs are more than just pets…they’re family and vital companions in our daily lives. With over a decade of hands-on experience caring for pets of all shapes and sizes (from geckos to Great Danes), I bring a calm, attentive, and knowledgeable approach to dog sitting and walking. I am currently in a mentorship and shadow program intensive to also become a dog trainer, so your dog will also get to practice some skills with me! My journey with dogs began early with family pets and expanded into dedicated pet sitting for neighbors and friends. As a lifelong learner, I’ve spent years studying dog behavior, body language, and communication styles through training my own dog. I have experience working with reactive dogs, maintaining strict routines, and using consistent, structure to make every pup feel safe and secure. I also regularly assist a close friend who is a professional dog trainer, which has given me great insight into handling diverse personalities, energy levels, and care needs. Outside of pet care, I work as a mental health therapist. My professional background deeply informs how I interact with animals. I understand the reciprocal bond between humans and their dogs, and I treat every animal in my care with the utmost empathy, patience, and respect. What to Expect Attentive & Safety First Care: Whether keeping up with medication, supporting structured routines, or managing triggers on walks, your dog’s safety and comfort are my top priorities. Active Adventures: I love helping dogs explore! If your pup enjoys an active lifestyle, I’m happy to take them along for hikes, trail walks, or gentle runs tailored to their fitness level. Tailored Communication: You’ll receive clear, regular updates and photos so you can have complete peace of mind while you’re away. Whether your dog needs a chill check-in, a structured neighborhood stroll, or a outdoor trail adventure, I’ll provide the exact same devotion, care, and attention I give to my own dog. I look forward to meeting you and your pup! I currently work from home as a mental health therapist. I am able to make my schedule and work around your pet’s needs as needed! There will always be time for potty and play breaks. I have a large yard, as well as my dog who is crate trained. If staying at your home, I would love to be clear on your pet’s schedule so they can have consistency. I also love having adventure buddies, so if your dog likes to be out in nature for trail walks or swims, I’m your gal!
“Kimm & Kenn have walked our (not so great on a leash) handsome man at a last minute notice and for an entire week before. We love how attentive they are and Tuck loves when they come.”
“Rebecca was so communicative for both of Pepper’s walk and took pictures both times, always a great relief for me. Pepper was obviously well taken care of and we will definitely be using Rebecca again!”
“Noila was wonderful, she stepped in at the last minute to walk my dog who had gotten sick and needed to be checked on. She was super responsive to changes to the schedule and was prompt with the walk.”
About: I know first hand how much love there is between a dog and their owner. For that reason, I believe trust, transparency, and fun are the pillars of my dog walking service. When you entrust me to care for your pet, I will make sure they are always safe, hydrated, and having fun! I also always send updates after walks letting clients know how the walk went and that dogs are home safe. As a dog owner, I have had family dogs ranging from a 6 lbs Yorkie to a 65 lbs Lab. Outside of my own pets, I have experience cat- and dog-sitting for friends and family and am excited to be able to take on more dog walking clients. I am comfortable walking dogs of many breeds, sizes and ages. I can't wait to meet your furriest family members! I am a graduate student, so I often have a flexible schedule to work around your needs. I am available for early morning and evening walks every day of the week and midday walks every day Wednesday-Sunday. Safety is my top priority for your pet, your home, and myself. This is why before working with your pet, I will request a meet-up with you to better understand your pet. In this meeting we can discuss if your pet has any aggression or fear around other dogs, escape-artist tendencies, or special needs so that walks can be as safe and secure as possible.
“Lauren has taken great care of my labrador retriever, Tanner, on days I have to go in the office. During our meet and greet she took notes specific to my dog and was super friendly! She asked a lot of questions and provided the best care I could ask for. Lauren provided updates and pictures of Tanner during his walks with her. I would recommend Lauren to all my friends with dogs.”
“Dogs’ expressions are honest and Tammy’s expression is one of happiness when going out for walks with Madeline. I rest easy at work knowing she is getting attention from and slow exercise with Madeline.”
“Always amazing! Cheryl is a god send to me and Frank. I have hired her in the past for a walk here and there but with a recent break in my ankle I need help more now than ever and she has been wonderful! Not only do I recommend her, my Frank would too! He absolutely loves his walks with her!”
About: Hi all! I have cared for pets on the side for the past few years. I am an animal lover. I have experience with sitting, walking, visits, and med administration. I am a Registered Nurse and a warm, loving person which definitely comes out in my work animals. I am super responsible, I have a flexible schedule and I am often available for last minute requests. I have experience with nervous rescue dogs, senior dogs, and very large dogs who pull on the leash. I live in East Boston but commute to Winchester often so I am available anywhere around those areas. I am super interested in getting to know you and your pets! Thank you so much and please feel free to ask my any questions that you may have.
“Getting my Rover Card from Lauren is always a highlight in my day! My pup always looks so happy and I feel great knowing he has company on a long day when he’d otherwise be alone.”
Over 980,000 dogs traded couch time for play time with Doggy Day Care on Rover1
Large dog specialists near you - Winchester
Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Our dog Chloe had an amazing stay with Yesika and we hope she is available in the future! She is loving and professional, and Chloe got plenty of exercise, playtime, and cuddles during her stay. Highly recommend.”
“Paul is just the best. Very communicative and makes pick up & drop off super easy. Love the frequent picture updates of our dog’s staycations. Gives us peace of mind that Thomas is getting constant care and attention when we’re out of town. Thankful to have found Paul on Rover and I know Thomas is, too! Highly recommend.”
“Guillermo is the best. He took very good care of our dog during our 2 weeks trip. He is gentle and patient with our anxious dog. He also gives us photos and updates everyday. Would definitely recommend him to people for pet sit next time!”
“Rob took wonderful care of our dog! Always responded quickly and seems like she had a great time! Definitely tired her out! Would definitely recommend him to anyone, and will be using him again if we go away.”
“I will definitely be rebooking with Rebeca! I could tell that she and her family truly cared for my dog, as they would their own. I received lots of photos and updates on her stay!”
“Maddy was so wonderful with my dog Jester!! We got tons of pictures and videos and you could tell how happy Jester was staying there. I was assured the whole time that my dog was well taken care of. We will use her again!”
“I had an absolutely wonderful experience with Linda! From the moment I met, it was clear how caring, reliable, and attentive she is. My furry baby was happy, well-exercised, and clearly comfortable the entire time I was away. Linda provided just enough regular updates and photos showing how cared for my baby was. It’s such a relief to know my baby was treated like family. I wouldn’t hesitate to book her again and highly recommend Linda to anyone looking for a trustworthy and loving sitter.”
“Luci and her family were so great with our Charlie! Pictures and updates every day made us very comfortable with leaving him behind! They were awesome. Highly recommend!!”
“Zelun was so good with our dog. We will definitely be using zelun in the future. He sent lots of photos and had great communication. He also brought Iggy on many adventures each day like the park and nice walks!”
“Ann and her husband took incredible care of our dog. She sent updates and photos regularly while we were away. She was also very accommodating with the drop off and pick up schedule, and was able to accommodate a last minute schedule change. It’s clear that Ann and her husband are dog lovers and go and beyond in their care. We will definitely use them again!”
“Janette and her family were so welcoming and loving with my dog, Ridley. We got lots of updates and photos of her enjoying her stay, and felt completely at ease leaving her in their care.”
“Our pets recently stayed with Nicole, and they loved being with her. Nicole sent updates and photos while we traveled which showed how much they were relaxed and enjoying their time with her. We highly recommend her to anyone looking for a someone to care for their pets while traveling.”
“Belinda was wonderful with our furbaby and sent us an update each day. She was very accessible by text and easy to communicate with. Our dog got along well with her dog, Sloane, who is a sweetie. Also, she has the perfect fenced in yard for the dogs to play! We will certainly work with Belinda again!”
“We boarded our dog and cat for a week. Likun is very experienced and attentive in taking care of both cats and dogs. We received daily updates and she also replied to our messages very promptly. Her Border Collie is so sweet and gentil. Our puppy was really happy she has a mature big sister and perfect playmate! The home is well equipped to take care of multiple pets and her backyard is perfect for dogs to play in.”
“Yang was absolutely amazing watching Tormund. She went above and beyond what I expected from my first time using Rover. She's going to be the first person I go to for any future dog sitting needs.”
“Katheryn was absolutely amazing with her care of our two greyhounds. She was very communicative and attentive to their needs. I highly recommend her and her husband and will trust her with our pets any time! Thank you!”
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