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%.
“Oana and Oliver were absolutely amazing and we are so appreciative that they took such wonderful care of our Frenchie, Indi! This was the first time we were leaving Indi with someone other than friends or family and were a bit tentative of the thought of it. However, Oana and Oliver were so thorough and dedicated to knowing her routine and health issues that they put us entirely at ease. Indi had an absolute blast with them during her long weekend stay and they kept us updated by sending a ton of pictures of her, which was so appreciated. We cannot say enough wonderful things about the care that Oana and Oliver put into keeping your furry friend safe and sound. We would absolutely recommend them and will certainly be using them in the future to look after Indi!”
“Mars had a wonderful time with Ann & Jim! They sent lots of photos, took him on adventures at the fells and walks featuring lots of fetch! He was happy to be there and came home tired and happy 🤗”
“Sam watched Wendy while we were out of town for a long trip and was so wonderful! She sent daily updates and photos of their walks and on how Wendy was doing - it was clear that Wendy was comfortable and in great hands. We would love to have Sam take care of her again!”
“Liz & Rodrigo are incredible people, with an incredible family full of love to give! We were a bit nervous having someone board our newly adopted rescue Beagle, but they did an amazing job! They sent so many updates and photos while I was gone, I never once had to worry how they were doing! They were both accommodating of both our pup’s needs and I can tell our pups would love to go back whenever we need a sitter!”
“This was my first time using Rover and Liz went above and beyond as Simon’s dog sitter. I received many pictures and updates every single day and there was no time lapse in her responses if I ever messaged her first. I’m not even sure Simon even missed me because of how well he was taken care of and loved on. Will most definitely be booking with Liz again and have raved about her to my friends with pets. Thank you again!!”
“This is not my first visit to Marilyn’s as my dog has stayed with her before. When I dropped her off this time, Maddie ran right to Marilyn’s husband, wagging her tail so hard I thought it she was going to take flight! Maddie loves staying with them. I think she sees it as visiting family! I have complete confidence in Marilyn and feel so lucky to have found such a wonderful place for her to stay when needed. She is a super nice person too. I would give her 10 stars if I could!”
“Guillermo took care of our dog Amos for nine days. He was an exceptional care provider. He went above and beyond taking Amos to the vet, giving his prescribed medication and even returning to the vet for a refill. Amos had plenty of walks. We received many pictures of Amos which my family really enjoyed. I would definitely re-book with Guillermo.”
“Jordan was absolutely fantastic! She treated Addie like she was her own! We were so happy that we booked our next boarding the same day we picked Addie up from this one!”
“Kate instantly made myself and Louie feel welcome and comfortable for his weekend stay! She sent me pictures and updates each day and I could tell Louie was happy and well cared for when I picked him up. I will definitely book her for future stays and highly recommend her!”
“Betsy was a great sitter - very thorough and careful in getting to know my dog’s preferences and letting him see her very nice home and yard! Easy to communicate with and my pup seemed super happy :)”
“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.”
“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!”
“I'm writing this review with gratitude as my heart is full. I booked a 16-day boarding for our dog, Pumpkin, with March recently. Our first meet and greet went well and we had two-30 min walks together within a few weeks to get Pumpkin familiar with March and the trails nearby. March sent me daily pictures of Pumpkin's activities, including walks and exploring around the house and his favorite spot, the kitchen! March treated Pumpkin like his own dog, and as part of his family, the same way we treat Pumpkin. He bought a dog bed from Cosco for Pumpkin as I didn't have the right kind. March also let Pumpkin went on his bed and sofas to watch TV with him. I think Pumpkin had a fantastic vacation at March's home! I highly recommend March for anyone looking for a dog-loving person with a sense of humor and pays a lot of attention to details.”
“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!!”
“Miley stayed with Aurora for 4 nights while I was away on a vacation. Her pup Madi and Miley became BFF’s. She sent regular updates and she was very prompt and quick responding to my texts. Miley is my daughter and I’m very nervous leaving her at someone’s place. But Aurora did a a great job taking care of Miley and treated her like her own pup. I would definitely like Miley to have her next vacation at her place. Adding to this their pup Madi is a wonderful dog very friendly.”
“Todd was awesome! Very communicative and attentive, and clearly seemed to provide a great environment for Beau to stay. He came home clearly taken care of, calm, and happy.”
“Ozzi had such a great time with Yang and her family. They welcomed him into their home and took great care of him. We received photos and videos every day to keep us updated, which was very appreciated. He will definitely go back on our next time away!”
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%.
“Charlotte was amazing! She took such great care of our kitties while we were away. We loved her photos and daily updates. She was super easy to communicate with and our nervous cat loved her! I highly recommend Charlotte and will definitely hire her again!”
“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”
“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!”
“Angela was great with our cat Onyx! She was very nice to chat with during our meet at greet assuring me he would be well cared for during her check ins! We were very happy with the pictures and communication while we were away and will for sure be using her again in the future!”
“I travel a lot for work and I have booked Jessica several times to take care of my cat while I’m away. She is very communicative and provides great updates so I know my cat is in good hands. Murphy loves her. Thank you Jessica!”
“Thank you, Jolene, for checking in on my two cats over a holiday weekend with a last minute booking! Jolene’s communication and timing was excellent. While checking on the cats, she filled their bowls, gave them treats, and brushed them. I appreciated her time and attention!”
“Cheryl is the best! We really appreciated her care and attentiveness. We would absolutely rehire her or recommend her to anyone looking for drop in visits for their cat!”
“Jillian took great care of our Bart and Bev! We could really tell from the pictures and daily updates that they warmed up to her and enjoyed her company. We felt totally comfortable with her in our home and appreciated how clean and tidy she left our apartment! Thank you Jillian!”
“Bonnie took excellent care of my cat. She provided detailed updates, which I appreciated even though I wasn’t always able to respond quickly because of the time difference. She also sent adorable pictures. She played with my cat and even brought her a new toy. She even cleaned (not just scooped) the litter box and replaced the litter, which I really appreciate.”
“I’ve had James watch my cat multiple times now and he treats him as if he were his own. This time I had a family emergency come up mid trip and James was super responsive and willing to extend the booking and help out last minute. Highly recommend!!”
“Yesika is an outstanding sitter. Trustworthy and consistent, she took care of my cat for several weeks during a long vacation. She is able to communicate well and I trust her to take care of any issues that may arise. I would highly recommend her for future pet visits and would definitely be interested in employing her again!”
“Ellie was amazing and took such great care of our 2 cats while we were away. She is caring and attentive, and our cats were comfortable with her immediately! She gave us updates each day along with some great pictures. This was our first time ever using a sitter, and we will 100% contact Ellie again in the future!”
“Meg is awesome! Good and easy communication. She sent me photos and videos and a detailed rover card every time she visited my cat, and it’s clear that my cat loved hanging out with her!”
“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!”
“Betsy was terrific. My cat warmed up to quickly and that isn’t usually the case. She went out of her way to play music for my cat who is a pretty sophisticated jazz aficionado! The cat seemed to enjoy it. A very caring person. I would use Betsy’s services again.”
About: Animals have been part of my life for as long as I can remember. I grew up surrounded by dogs, cats, birds, fish, turtles, hamsters, gerbils, and even chickens — and each one taught me something different about patience, joy, and unconditional love. Over the years, I’ve rescued dogs, helped others find their forever homes, and volunteered at shelters and adoption events. To deepen my skills, I’m completing a pet CPR and first‑aid certification. This training covers CPR techniques, choking response, and emergency care for injuries or poisoning, giving you peace of mind that your pet is in safe hands. I love working with cats and have experience with basic grooming, brushing, and keeping litter areas clean and comfortable. Your pets are family, and I’ll care for them with the same love, patience, and attention I give my own.
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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%.
“Janette and her family, including their dog Luna, are so wonderful to our dog, Lenny. She is so kind and communicative! Lenny loves spending time with them and going for walks in their beautiful neighborhood. Thank you so much for taking such great care of our dog!”
“Surendra was so nice to jump in last second when another sitter cancelled on me. Daario looked like he had so much fun in all the photos I received and both him and his wife are great at communication! Would love to rebook anytime :) thanks”
“Oana and Oliver are wonderful dog sitters!! They are kind, easy going, and always send the best pictures! We had an extenuating circumstance with our trip and they were completely accommodating and understanding. I highly recommend them for all doggy daycare and sitting needs!!”
“Elizabeth and Neil made our anxious goldendoodle feel right at home! They were so great with him, gave him lots of love and attention, and communicated excellently with us, sending lots of great photos and videos throughout his stay.”
About: Since coming to college, I’ve started volunteering at the Humane Society where I’ve been day-fostering! Love dog sitting/walking for friends and neighbors. Would be more than happy to take care of your pups :) I’m a college Senior with a light course load this semester and plenty of free time, especially on weekends. My schedule is normally pretty consistent with classes from 12-2pm. Outside of those hours I’m very flexible! I have no pets at my home and have the energy to entertain your pet (no matter how energetic they are). I’m a safety-first kind of person and big on communicating any areas of uncertainty!
“My puppies have stayed with Carol a few times and they always have so much fun! She sends me pictures and videos all day and the pups are exhausted when I pick them up which is nice!”
About: Master's degree in animal care and welfare. Former vet tech for dogs and cats at an E.R. I also have an Animal Science degree and have cared for horses and other animals. I work from home some days, part-time, and always have walk breaks. I go for long walks and will join with doggy playmates if your dog is able. Will also walk small dogs in carriages for fresh air. Have fenced in yard for small and medium size dogs. I have a fenced in yard and one Bichon rescue dog who is older, and friendly with other dogs. I was a former vet tech and have much cat and dog health care skills.
“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!!”
“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!!”
“Took my greyhound, Judy, to stay with Luci and her family for 2 doggy daycares. Judy is typically timid around new environments but warmed up quickly to them and absolutely loved spending time with everyone and the other dogs being watched. Definitely will be using Luci again!”
“A truly 5 star experience. Cameron was easy to communicate with and work with. Just off vibe alone I knew my dog was in good hands when he was picked up. Throughout the day I was consistently updated with photos and videos of my dog out and about. I highly highly recommend Cameron to anyone in need of a dog-sitter. Next time I’m in Boston I will 100% be reaching out to him first. Finn will miss Cameron and Rosie a ton!!! 5 stars!!”
“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!”
“Elizabeth and Rodrigo were great with Oscar. They were flexible when I needed to shift my drop-off and pickup times, which made my day so much easier. They sent a few photos throughout the day too, which I always love getting. Oscar came home tired and happy, so he clearly had a good time. Would book with them again in a heartbeat. Thanks you two!”
“Samantha is amazing ! She is kind, communicative, and personable. It’s obvious she is an animal lover. She watched my dog Teddy for the day and he was happy and relaxed when I picked him up. Highly recommend !”
“Ben and his family took great care of Zelda and were very accommodating of our busy schedule. She came home happy and well exercised from playing with their pups all day. We will definitely book with Ben again!”
“Cheuck was an excellent sitter for our dog Simka. We basically never leave her with someone we don’t know, but he made us comfortable from the beginning and she had a great time. It was fun to see photos and videos throughout her stay.”
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%.
“Olivia was great! She communicated well which is key! She took Cindy for a nice walk and sent us photos so we new she was getting attention while we were away. Would love to have her again!”
“Shawn is wonderful with our girl Apple! She is so kind, patient, and very trustworthy - we all immediately liked her and are so grateful that she can help us with our pup 😊”
“Extremely dependable and arrives exactly when promised - she was so prepared that she even brought towels to dry off the dogs when it was very wet outside! Thanks again!”
About: Spent extensive time caring after my families dogs & cats as well as the pets of my neighborhood. I also look after my friends cats and dogs of Boston and Maine. Comfortable with walking, playing with, feeding, and even some light training with dogs. I don’t have certifications with dog training but I would be happy to reinforce training you do with them for some light commands. I work in sales in a fairly fluid environment. I spend some time at home and the rest of my time around the city and greater Boston. Drop in pet care/walking fits perfectly into my schedule as I can work from my computer and travel when needed. I do have a fenced in yard but I’m not currently accepting pet care in my own home outside of the critters I already have. I may open up to this in the future but I do use a lot of space In my car already.
“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.”
“I really appreciate the time and consideration Angela had with Maple! She was mindful of length of the walks during hot days and spent the rest of the time watching Maple. I can tell Maple had a great time with her! Highly recommend!”
About: I have been around animals all my life. Grew up in the rural Midwest surrounded by dogs, cats, rabbits, hamsters, turtles, in addition to the cows, pigs, chickens, and horses at nearby farms. I love animals and have helped care for them all my life. I am comfortable with all kinds and sizes of dogs and love getting them out on walks/hikes and playing with them, snuggling with them indoors as well. I adore dogs and remain calm, letting them get used to me before trying to engage...letting them set the stage or lead the way. Once I get to know them I am very affectionate with them and love to play and run around with them. I currently live in my own place with my cat and would love to care for your pets in your home. I'm currently between jobs and thought I would get back to pet sitting/walking for now. I love hanging with my furry friends and getting out for brisk walks! I will spend time getting to know your pet, snuggling with them(if they want), getting them outdoors and playing with them, keeping them on their feeding schedule and caring for them like they're my own.
“Took amazing care of my babies and kept me updated throughout their walk. She was very friendly and my anxious Chihuahuas immediately loved her energy and were pulling to greet her. All around would recommend Sanela!”
“Rebecca was wonderful! She took the time to come meet Mr. Lahey before care and he immediately could tell she was a true animal lover! Did a wonderful job caring for him, as well, and very good at communicating! Highly recommend Rebecca for all your pet needs haha”
“Cheryl is great! My pup had torn up her bed and left stuffing everywhere and Cheryl made sure it was picked up and safe before she left! Very helpful and kind! Will definitely book again”
About: I have a lot of love for every pup I meet. I grow a bond with them more than most people would ever even try. I like to treat my clients dogs the way I treat my own two dogs. I would want my dogs to be taken care of as passionately as I do. I am available any day any week at any time! I have a flexible schedule because of I attend online college! Very excited to begin!! I treat them with love and respect. I do not go past boundaries by making the pet feel unsafe in any way or making them feel anxious. I like to give them time and space to adapt to me so we can become even closer in the future!
About: Animals have been part of my life for as long as I can remember. I grew up surrounded by dogs, cats, birds, fish, turtles, hamsters, gerbils, and even chickens, and each one taught me something different about patience, joy, and unconditional love. Over the years, I’ve rescued dogs, helped others find their forever homes, and volunteered at shelters and adoption events. I have a soft spot for senior pets and pups with special needs. My dog Dumba is turning 16 this February, and supporting her through her golden years has taught me how to be gentle, attentive, and adaptable. Before Dumba, my dog Cookies bravely fought cancer for many months, and I cared for him through two surgeries and ongoing treatment. Because of experiences like these, I’m comfortable administering medication, monitoring health changes, and giving extra support to pets who need a little more care. I also love working with cats! Since rescuing Zoro when he was only 8 weeks old, I have developed experience with basic grooming, brushing, and keeping litter areas clean and comfortable. Your pets are family, and I’ll care for them with the same love, patience, and attention I give my own. My schedule is flexible, and I’m happy to accommodate your pet’s routine. I'm currently offering daily walks and drop‑in services. I live in Winchester and know the area well, so your dog can enjoy peaceful walks around Horn Pond or fun playtime at Sheepfold Dog Park. I share my home with my senior dog, Dumba, and my goofy cat, Zoro. They’re both used to being around other animals, but my space isn’t large enough to comfortably or safely host additional pets. Because of that, I offer care exclusively in your home, where your pet feels most secure and where their routine stays consistent. When I’m caring for your pet, I follow your house rules and make sure your pet’s environment stays familiar and stress free. My goal is to respect your home, maintain your pet’s routine, and give them attentive, loving care while you’re away.
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%.
“Mars had a wonderful time with Ann & Jim! They sent lots of photos, took him on adventures at the fells and walks featuring lots of fetch! He was happy to be there and came home tired and happy 🤗”
“Sam watched Wendy while we were out of town for a long trip and was so wonderful! She sent daily updates and photos of their walks and on how Wendy was doing - it was clear that Wendy was comfortable and in great hands. We would love to have Sam take care of her again!”
“Liz & Rodrigo are incredible people, with an incredible family full of love to give! We were a bit nervous having someone board our newly adopted rescue Beagle, but they did an amazing job! They sent so many updates and photos while I was gone, I never once had to worry how they were doing! They were both accommodating of both our pup’s needs and I can tell our pups would love to go back whenever we need a sitter!”
“Patrick was great and super responsive, sending me pictures of Albie throughout the day/ night he stayed with him. He also was thorough in making sure he understood Albie’s needs at the start of his visit, which made it even smoother. Would definitely ask him to watch Albie another time!”
“This was my first time using Rover and Liz went above and beyond as Simon’s dog sitter. I received many pictures and updates every single day and there was no time lapse in her responses if I ever messaged her first. I’m not even sure Simon even missed me because of how well he was taken care of and loved on. Will most definitely be booking with Liz again and have raved about her to my friends with pets. Thank you again!!”
“This is not my first visit to Marilyn’s as my dog has stayed with her before. When I dropped her off this time, Maddie ran right to Marilyn’s husband, wagging her tail so hard I thought it she was going to take flight! Maddie loves staying with them. I think she sees it as visiting family! I have complete confidence in Marilyn and feel so lucky to have found such a wonderful place for her to stay when needed. She is a super nice person too. I would give her 10 stars if I could!”
“Guillermo took care of our dog Amos for nine days. He was an exceptional care provider. He went above and beyond taking Amos to the vet, giving his prescribed medication and even returning to the vet for a refill. Amos had plenty of walks. We received many pictures of Amos which my family really enjoyed. I would definitely re-book with Guillermo.”
“Jordan was absolutely fantastic! She treated Addie like she was her own! We were so happy that we booked our next boarding the same day we picked Addie up from this one!”
“Kate instantly made myself and Louie feel welcome and comfortable for his weekend stay! She sent me pictures and updates each day and I could tell Louie was happy and well cared for when I picked him up. I will definitely book her for future stays and highly recommend her!”
“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.”
“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.”
“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!”
“I'm writing this review with gratitude as my heart is full. I booked a 16-day boarding for our dog, Pumpkin, with March recently. Our first meet and greet went well and we had two-30 min walks together within a few weeks to get Pumpkin familiar with March and the trails nearby. March sent me daily pictures of Pumpkin's activities, including walks and exploring around the house and his favorite spot, the kitchen! March treated Pumpkin like his own dog, and as part of his family, the same way we treat Pumpkin. He bought a dog bed from Cosco for Pumpkin as I didn't have the right kind. March also let Pumpkin went on his bed and sofas to watch TV with him. I think Pumpkin had a fantastic vacation at March's home! I highly recommend March for anyone looking for a dog-loving person with a sense of humor and pays a lot of attention to details.”
“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!!”
“Miley stayed with Aurora for 4 nights while I was away on a vacation. Her pup Madi and Miley became BFF’s. She sent regular updates and she was very prompt and quick responding to my texts. Miley is my daughter and I’m very nervous leaving her at someone’s place. But Aurora did a a great job taking care of Miley and treated her like her own pup. I would definitely like Miley to have her next vacation at her place. Adding to this their pup Madi is a wonderful dog very friendly.”
“Todd was awesome! Very communicative and attentive, and clearly seemed to provide a great environment for Beau to stay. He came home clearly taken care of, calm, and happy.”
“Ozzi had such a great time with Yang and her family. They welcomed him into their home and took great care of him. We received photos and videos every day to keep us updated, which was very appreciated. He will definitely go back on our next time away!”
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