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%.
“Yang was so great with our dog! We got daily updates with pictures and videos. She was also so wonderful to us, our flight was canceled and rescheduled for 2 days later. Luckily we were able to get out the following night but Yang was so accommodating and kind while we were in a state of worry. Lucky will be back in a few weeks for a second stay!”
“Betsy and her family were wonderful hosts for our pup. Betsy sent pics and videos, and Ronja seemed to have a fantastic time. Great communication, we felt safe leaving our dog in Betsy's care.”
“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.”
“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 🤗”
“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!”
“Our dog Anfi is a shy and very anxious girl. We’re usually unable to leave the house without her due to her separation anxiety, but thanks to Linda that’s no longer the case! Linda has been so amazing. She has treated Anfi with much love and care, and we are so appreciative of that! We look forward to many more day care and boarding stays with Linda!”
“Guillermo was absolutely amazing with our dog, Lola. He took such great care of her and kept us constantly updated with messages and photos, which really put us at ease while we were away. It’s never easy leaving your pet behind, but Guillermo made the whole experience completely stress free. We could tell Lola was happy, comfortable, and very well cared for the entire time. We’re so grateful for his attentiveness and kindness, and we would 100% trust him with Lola again. Highly recommend!”
“I can’t say enough amazing things about Likun—she is truly the BEST dog sitter we’ve ever had! From the moment Chewy arrived, he was showered with so much love, attention, and care. 🐾💛 She spent tons of time playing with him and made sure he was always happy and engaged. Her large backyard was an absolute dream—plenty of space for Chewy to run around, explore, and have the time of his life! It honestly felt like a mini vacation for him. What really stood out was the 1-on-1 attention she gave him. You can tell she genuinely cares about the dogs she looks after, and Chewy absolutely adored her. I picked him up relaxed, happy, and clearly very well cared for. If you’re looking for someone trustworthy, attentive, and full of love for your pup, Likun is it. We will definitely be booking with her again—Chewy can’t wait to go back!”
“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.”
“Tamale was taken care of so well while we were away! Luci and her family loved having her there, and were always timely with food, supplement, and routine updates. They took her on multiple walks and even a dip in the pond while she was with them. We are so grateful to the service and will be having them sit for Tamale when we are away next!”
“Our pup was happy in every picture & very excited but quickly calm when she got home, which to me says that she was happy to be home, but didn’t feel nervous at Aurora’s home! Aurora also was diligent to make sure our counter surfing, sneaky dog didn’t get human food during her stay. We will definitely book with Aurora again!”
“Jonathan is an exceptional dog-sitter, our pet was very well cared for, exercised, and received lots of affection and attention. Jonathan was also very accommodating when we needed to extend our stay by a day at the last minute. Would recommend and will certainly book with again!”
“Lori was great! This was my first time leaving my pup and she made it a great experience! Lori was great with the dogs, has a fenced in yard and sent me videos of my pup playing and having a blast! I’ll be sure to use Lori again!”
“"It's as if she never left!" - Our dog Bella has stayed with Rob several times, and was delighted to be back. Rob and his family take great care of her (walks, feeding, treats, loving) and make her feel a part of both the people and dog families!”
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%.
“Cheryl is WONDERFUL. She is caring, attentive, and clearly loves her work. I felt so at ease leaving my fur baby in her care, and she made sure he was well taken care of down to the last detail. Would highly recommend!”
“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!”
“James dropped in on our cat for us while we were away for a weekend and did an amazing job! From sending hilarious pictures and videos while spending quality play time with her to going above and beyond by dealing with some house issues that arose, we could not have felt that she was better taken care of. And I think she found a new best friend!”
“Sophia did a great job taking care of Oreo and giving her lots of playtime and cuddles! She also kept a consistent schedule and was on top of all the daily responsibilities, will definitely book 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 did a great job and took very good care of our cats, including making sure on of them got her pills. She clearly cares a lot about cats and was very communicative, including lots of pictures.”
“Sanela was lovely! She became cuddle buddies immediately with our cats. Great with communication. Her check in comments, pictures, and punctuality immediately calmed any anxiety we had about leaving our boys.”
“Ellie was a joy to work with!! we needed a cat sitter fairly short noticed for a holiday weekend - Ellie was great with our guys, attentive to their special needs & always sent updates / detailed rover cards which was great info to have! We Will definitely use Ellie again 🥰”
“This is our third time having Caitlin come to check on our two cats and as always she does a great job looking after them! Great at providing daily updates and responsive when we need to get in touch. Always appreciate the work that Caitlin does, highly recommend!”
“Galina took very good care of my two cats! Despite their shy nature, they warmed up to her quickly and enjoyed her company while we were away. She is easy to work with and very communicative.”
About: What sets me apart from other sitters is my lifelong experience with cats and my attention to detail. I’ve cared for cats of all ages—from energetic kittens to senior cats needing medication and extra TLC. I’m comfortable administering oral medications and sticking to specific feeding or care routines. I take pride in keeping litter boxes clean and tidy because I know how important a fresh, sanitary space is for a cat’s comfort. Most importantly, I respect each cat’s unique personality and pace—whether they’re shy, playful, or a little bit of both.
“Yesika did an amazing job with my 1-year-old cat, Timmy. She was communicative, thoughtful, and extremely knowledgeable. She followed all of my instructions for visits and sent detailed updates. He had a skin irritation that popped up just before I went away, and she was so helpful in taking care of his skin on top of everything else. I felt so much less stressed being away from him knowing she was there! I will absolutely hire her again.”
“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!”
“Natalie was able to help me out last minute and im incredibly grateful for her. She’s so good with the cats and sent several pictures as always. Thank you for everything!”
“Jillian was great! Super attentive and communicative while staying with my cats and tortoise. I’m definitely a high maintenance, nervous owner and I felt very comfortable leaving my pets with her.”
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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%.
“Belinda took great care of our dog Ollie and sent regular updates and pictures. Ollie is an anxious dog and he seemed very comfortable there. We would definitely have him stay with her again!”
“My pup had the best time ever in the yard, chilling in the house, and befriending Betsy’s sweet dog. I even got a photo during the day. :-) Looking forward to her next stay!”
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.
“This is Scout's second time at Jacqueline's for doggy daycare. She and Harley do an amazing job looking after Scout. Highly recommend her, she treats your dog as if it were her own.”
“Another great stretch of daycare days with Likun and EL! He races to her house every morning which tells me he loves going! I can go to work knowing he’s in good hands. Thank you again!”
“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!”
“Wonderful family who provided care for my pup last minute. They sent me pictures throughout his stay and he appeared happy and tired from all of his play with their other dogs when I picked him up!”
“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!”
“Ben was super flexible with our schedule and very quick to respond / help us out. The whole family jumped in to keep our pup well engaged all day, and we sincerely appreciate their support. Will absolutely reach out again when in need!”
“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.”
“Elizabeth and Neil are so attentive to my Honey bun! They are true animal lovers and provide the best play space! So thankful to have people I can trust when I’m at work! Small play groups with repeat clients creates such a fun group of pups. Honeys new bestie is Zoey ❤️”
“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.”
“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!!”
“Lexi took great care of Emmy during her daycare visit! She was very attentive to Emmy’s needs and made sure she felt comfortable and happy throughout the day. We appreciated all of the updates Lexi sent us during the visit!”
“Marcia was absolutely wonderful! She is incredibly kind and clearly loves animals. I received frequent updates with photos and videos throughout the day, which really helped to ease my mind. I loved the videos watching my dog, Mylo, get to play with Marcia and Cosmo! My high-energy puppy came home happy and exhausted, which is the best compliment I can give considering Mylo’s energy level! I highly recommend Marcia to any pet owner looking for a loving and responsible sitter.”
“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!”
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%.
“My stranger reactive dog has come SO far with Ryan’s help. He went from growling and lunging from our front porch when he saw Ryan to excitedly greeting him at the door. Every week Ryan has worked patiently with my dog, gradually teaching Bandit to trust him and how to be more brave when confronted with fears and triggers. I can’t stress enough how amazing Ryan is. If I could give him 6 stars I would!”
“Very professional, thoughtful and thorough services! I was very happy that I was able to leave my dog home without any worry and he was taken care of very well! Parker (although not into people much) seemed to really like James's energy and went out with him no problem. I hope we will be able to use James' services in the future.”
“So sad to be moving as Cheryl was the best dog walker. She was always available with my chaotic schedule. My dog loved her almost as much as he loved her homemade treats. Highly recommend Cheryl.”
“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 😊”
About: I’ve been around dogs my entire life and have experience caring for pets for family, friends, and neighbors. As a retired Division I student-athlete and current graduate student at Tufts, I am dependable, responsible, and highly organized. I understand that pets are family, and I treat every dog as if they were my own. One thing that sets me apart is my patience and ability to adapt to each dog’s unique personality. I have experience working with anxious, timid, and shy dogs who need extra reassurance, as well as high-energy dogs who thrive with exercise, structure, and play. As a former Division I athlete, I am also comfortable handling larger, stronger dogs and can confidently keep up with dogs that need long walks, runs, or plenty of activity. Whether your dog needs exercise, playtime, lots of attention, or simply a reliable person to check in on them, I’m happy to help. Your pet’s safety, comfort, and happiness will always be my top priorities. I also provide regular updates and photos so you can have peace of mind while you’re away. I’m a graduate student at Tufts University with a flexible schedule that allows me to provide reliable pet care throughout the week. I enjoy staying active and spending time outdoors, so dog walks fit naturally into my daily routine. Whether your pet needs a quick potty break, a long walk, or a drop in visit, I’m committed to being dependable, punctual, and responsive. Your pet’s safety and comfort are my top priorities. I take the time to learn each pet’s routine, personality, and specific needs so they feel secure and cared for while you’re away. I will always follow your instructions closely, keep pets safely leashed during walks, and provide regular updates and photos for peace of mind. I treat every home with respect and every pet as if they were my own.
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.
“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!”
“Noila was very prompt and walked Miles without any issues. She had a last minute adjustment close to the time and had to modify the booking, but she was very apologetic and professional about it. We would definitely use Noila’s services again.”
“Sophia was such a pleasure to work with. Sophia came on time and collected Dakota and Bogomila on a walk replete with photos and helpful commentary. I look forward to working with Sophia in the future”
“Jacqueline is awesome! So patient with my crazy, energetic pup. Piper absolutely loves when Jacqueline comes for her walks and waits for her to return when she leaves!”
“Olivia is great! She was punctual, easy to communicate with, and comfortable walking my 55 pound (one year old) dog, who tends to pull on the leash. I would happily hire her again!”
About: I've always loved taking care of dogs! I had my first when I was 9, a beagle. Throughout the years I've done various dog-walking and dog/cat sitting for friends and family, and now I miss seeing all the dogs as I live away from them and they have passed :'( On multiple occasions, I took care of two loving but rambunctious pit bulls for weekends and extended periods of time while my friend was away. Gave them medicines, lots of attention, and invigorating walks. I took care of the house while they were away and sometimes stayed overnight. I have experience with dogs that need to be on a tight leash in certain scenarios, and experience allowing them to just have fun in safe spaces. With well-behaved dogs, I've gone on runs in the forest and been able to have them off-leash. I love having a buddy! I care a lot about maintaining the boundaries and rules around how you have trained your pet and keeping their routines. I manage an office nearby Monday thru Thursday, flexible Fridays. The morning walks are reliable and I can message you specifics and sort your dog’s and my schedule around it :) Most days, the afternoon walk can be configured into the schedule. We have a larger yard and no pets living in the house. My sisters nearby both have friendly dogs if yours would like some pals. Some days are busier or have a tighter walk schedule for me, but usually just 2 weekdays, which is why this works for me! I love taking dogs to different adventures like the Fells or games in my backyard, or just hanging out and cuddling :)
About: I’ve had dogs and cats my entire life, so I’m very comfortable caring for pets of all ages and personalities. I’m patient, dependable, and attentive to each pet’s individual needs, whether that means going on walks, playing, feeding, administering basic care, or simply providing companionship. I understand how important it is for pets to feel safe and loved while their owners are away, and I’ll treat every pet as if they were my own. My lifelong experience has taught me how to recognize changes in behavior and ensure pets stay happy, healthy, and comfortable. Pet care is a large part of my daily life. In my home we have two cats (Max and Binx) and one extra large Labrador (Trixie). I change litter, feed my pets, and take Trixie out to the bathroom and for walks. Although I haven’t professionally cared for clients’ pets yet, I’ve had dogs and cats my entire life and understand the responsibility that comes with caring for them. I always make sure pets have fresh food and water, plenty of exercise, attention, and a safe environment. I’ll carefully follow any instructions provided by owners to keep their pets comfortable and maintain their normal routine. I treat every animal with patience, kindness, and the same level of care I give my own pets.
“Rebecca was wonderful! My pup, Cleo, loved walking with her! Cleo can be anxious around new people but warmed up quickly. Rebecca even came by the house a few days earlier to meet Cleo which I thought was really great! Also, given that Cleo has only been in my life for two months and I am a first time dog mom, Rebecca gave me some helpful tips too!!”
About: I’ve grown up caring for a wide range of animals and have extensive experience walking both small and large dogs; rain or shine. I tailor each walk to your dog’s needs, whether that means a relaxed pace or a more active outing while equally maintaining any training routines you’ve established. I’m also experienced with senior dogs and can provide gentle walks, rest breaks, or additional support as needed. Your dog’s safety, comfort, and happiness are always my top priority! I am a freshman university student returning back home to Massachusetts for the summer, currently working part-time. I am free most days for regular walking, but will be occupied Monday and Wednesday evenings for extracurricular classes. I am generally flexible and will manage to work around your schedule! I provide reliable and respectful in-home visits, ensuring your dog is cautiously handled and returned as instructed. I carefully follow your instructions, including access, routines, and any specific care needs, so your pet’s day stays consistent. You can trust that I treat your home and your dog with the utmost professionalism at all times.
“Cathalina took our dog for a walk and he had a great time! She is so friendly and very responsive. Sent some cute photos of him while they were out. Will definitely be using her again in the future”
“Lisa was great with my dog, Milo! She truly cared for Milo and was very diligent in following any of my requests. I would definitely recommend Lisa for any pet care needs. She’s dependable, thoughtful, and my dog really enjoyed his time with her 😊”
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%.
“Yang was so great with our dog! We got daily updates with pictures and videos. She was also so wonderful to us, our flight was canceled and rescheduled for 2 days later. Luckily we were able to get out the following night but Yang was so accommodating and kind while we were in a state of worry. Lucky will be back in a few weeks for a second stay!”
“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.”
“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 🤗”
“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!”
“Our dog Anfi is a shy and very anxious girl. We’re usually unable to leave the house without her due to her separation anxiety, but thanks to Linda that’s no longer the case! Linda has been so amazing. She has treated Anfi with much love and care, and we are so appreciative of that! We look forward to many more day care and boarding stays with Linda!”
“Guillermo was absolutely amazing with our dog, Lola. He took such great care of her and kept us constantly updated with messages and photos, which really put us at ease while we were away. It’s never easy leaving your pet behind, but Guillermo made the whole experience completely stress free. We could tell Lola was happy, comfortable, and very well cared for the entire time. We’re so grateful for his attentiveness and kindness, and we would 100% trust him with Lola again. Highly recommend!”
“I can’t say enough amazing things about Likun—she is truly the BEST dog sitter we’ve ever had! From the moment Chewy arrived, he was showered with so much love, attention, and care. 🐾💛 She spent tons of time playing with him and made sure he was always happy and engaged. Her large backyard was an absolute dream—plenty of space for Chewy to run around, explore, and have the time of his life! It honestly felt like a mini vacation for him. What really stood out was the 1-on-1 attention she gave him. You can tell she genuinely cares about the dogs she looks after, and Chewy absolutely adored her. I picked him up relaxed, happy, and clearly very well cared for. If you’re looking for someone trustworthy, attentive, and full of love for your pup, Likun is it. We will definitely be booking with her again—Chewy can’t wait to go back!”
“Tamale was taken care of so well while we were away! Luci and her family loved having her there, and were always timely with food, supplement, and routine updates. They took her on multiple walks and even a dip in the pond while she was with them. We are so grateful to the service and will be having them sit for Tamale when we are away next!”
“Our pup was happy in every picture & very excited but quickly calm when she got home, which to me says that she was happy to be home, but didn’t feel nervous at Aurora’s home! Aurora also was diligent to make sure our counter surfing, sneaky dog didn’t get human food during her stay. We will definitely book with Aurora again!”
“Jonathan is an exceptional dog-sitter, our pet was very well cared for, exercised, and received lots of affection and attention. Jonathan was also very accommodating when we needed to extend our stay by a day at the last minute. Would recommend and will certainly book with again!”
“Lori was great! This was my first time leaving my pup and she made it a great experience! Lori was great with the dogs, has a fenced in yard and sent me videos of my pup playing and having a blast! I’ll be sure to use Lori again!”
“"It's as if she never left!" - Our dog Bella has stayed with Rob several times, and was delighted to be back. Rob and his family take great care of her (walks, feeding, treats, loving) and make her feel a part of both the people and dog families!”
“Patrick took great care of my dog over Thanksgiving. He was communicative during the planning process and while he was sitting my dog, he sent daily videos and updates. Highly recommend Patrick!”
“Michelle & Michael are the ultimate pet sitters for my young dog, Ruby. She clearly receives an abundance of care, love and attention, as her sweet, expressive & energetic personality is in full effect, which only comes out when she is completely comfortable with people. I feel very lucky to have found them, and they are first on my list! Thank you, Michelle & Mike! :)”
“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!”
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