Dog Sitting in Winchester
Book a Winchester dog sitter to watch your dog in your sitter’s home or yours.
Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Winchester dog sitters
Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
About: I’m reliable, flexible and a good communicator, who loves to spend time with your fur babies, whether it’s cuddles, play or a long walk in the woods. I’m a teacher who has lots of flexibility this summer! I have my own strong and active 45 pound rescue, Sox, and have walked many neighbors’ dogs and helped my kids with their own dog walking businesses. I’d love to meet your pup! I’m a teacher, currently off for summer vacation, so I have a lot of flexibility June, July and August. I may often be available last minute, as well. I have a car, and am comfortable entering and exiting your home. (My own dog greets people with a whole lot of barking, so I’m used to that!)
“Sophia got my fairly shy cat out to play and even brushed her which I can’t believe she got my cat to do! Sophia is great and was very flexible with my schedule. I would have her cat sit again anytime.”
“Angie did a fantastic job of taking care of my old kitty. She was very responsive and we really appreciate her alerting us to a potential issue for a pet that wasn’t her responsibility!”
“We recently moved to a new apt and needed a new sitter for our 10 year old kitty. Carol did a great job with her in all ways. Carol kept her routine and spoiled her the way we do. Our cat was relaxed and well taken care of by Carol. Highly recommend her pet services.”
“Again Caitlin helped us within less than a days notice and within 24 hours! Our cat seemed to enjoy playing with her and she checked the litter box for me as well as refreshing the food and water! Will use ongoing for both pets.”
“Hillary was a great find in the "eleventh hour" of my search for service. She dropped in and took really good care of my dog while I was far away for the day. I felt confident from our first texts and Hillary's generous effort to come to my home for a meet n greet. Hillary followed through with great communication, lots of photos and follow up texts. I would call her again in a heartbeat and highly recommend her services ! Thank you so much!”
“Maria and her partner happily accepted a quick meet up before meeting Mochi and I. They were eager, friendly, and very respectful. They spent and hour each day playing, petting, chasing, and cuddling with Mochi. My little Mochi was ecstatic to see them and play with them. Knowing that she was in great, eager, and safe company and while providing her nonstop attention for the hour was the best I could ask for. Would love to have Maria and her partner hang with Mochi again soon!”
“Took excellent care of my Lab, Lenny, and left my house in perfect condition. Santhie is also so warm and kind, and made sure to ask all questions necessary to learn Lenny’s routines. I would highly recommend her services and look forward to scheduling more drop-ins in the future!”
“We can’t say enough good things about Yuzhou! She has been absolutely amazing with our dogs—so caring, patient, and attentive. Our pups are always sooo excited to see her and come home happy and well-exercised after every walk. We also love the detailed updates she sends after each visit—it gives us such peace of mind knowing the boys are so well cared for. Yuzhou truly treats our pups like family, and we feel so lucky to have her!”
“Blane was super organized— reached out in advance to come meet the kitties and see the house. The updates we got were so full of love and we 100% knew the cats were in good hands. It was also very easy to ask for a few extra things like making sure the AC was on and the windows were closed when the weather changed. Thanks so much!! We’ll definitely be repeat customers.”
About: For the past few years now I’ve been a dog sitter for my family and friends, walking, playing, feeding, and cleaning up after them I can house sit, dog walk, and do drop in visits, Any time of the day Mondays to Fridays, And weekends if needed anything works. I get to learn pets usually routine. How many times a day to walk them, when and how to feed them, and their bed time.
About: I worked overnight at the PetSmart Pet Hotel for 2 years, taking care of both dogs and cats—feeding them, cleaning up, and making sure they were safe and comfortable through the night. I got a lot of experience with all kinds of personalities, from super energetic to shy or anxious pets. I’m also a K–8 paraprofessional, so I’m very patient, responsible, and used to being on my feet and handling a lot at once. I have a really bubbly, caring personality and genuinely love spending time with animals and making them feel happy and safe. With summer coming up, I have more free time and would love to spend it taking care of your fur babies! I’ll treat them like they’re my own and make sure you feel totally comfortable and they stay safe. I work as a K–8 paraprofessional during the school year, so I’m available in the afternoons, evenings, and weekends. With summer coming up, I’ll have much more flexibility and open availability. I have plenty of time and energy to give your pets attention, playtime, and care throughout the day! Your pet’s safety and comfort are my top priorities. I follow whatever routine your pet is used to, including feeding schedules, walks, and any special instructions. I’m very attentive and used to handling different personalities from my time at the PetSmart Pet Hotel. I’ll make sure your pet feels safe, loved, and well cared for, and I’m happy to send updates so you feel at ease while you’re away.
About: I have experience with dogs of every size! I walk, run, bathe, feed, and have taken care of the pets of friends and neighbors for years. I love taking long walks in the fells or around town with my dog daily, I can do early morning walks, late night, or whenever! I can spend as much time as you need taking care of your pets in your home. I can feed, check-in on, play with, or just spend time with your dogs!
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.
“Kathryne took excellent care of our 2 dogs and at last-minute notice! She was very responsive to messages and flexible when there was a slight schedule change. Would not hesitate to book again!”
About: I've had pets growing up, and I was the main one caring for them. I've had dogs, a cat, guinea pigs, bunnies, fish, and a hamster. I love all animals, but mainly a dog lover! I have watched friends and family's pets. I did the basic care needs: walking, feeding, giving water, playing, and showing lots of love and attention. With my current dog, I have had to give her pills, so I also know different ways to give pills to dogs. I also know how to teach basic commands such as sit, stay, paw, and high-five. When I used to live in Texas, I volunteered to take a shelter senior dog for the day. I did basic care needs and even took him walking/running in a field before taking him back. I currently work a full-time job, anywhere from 7am-6pm on weekdays but I am free on weekends. I also don't mind going after work if you need someone to take your fur babies on a walk, do a check-in, or need to be fed/given water! I live with my boyfriend's family so unfortunately, I can't care for pets in my home. I don't mind just going to your house/apartment to care for your fur babies. I can take them for walks, play with them, keep them company, feed them, give them water, or even take them out the house for a little (a drive or even a walk around a store that allows pets).
“Needed a sitter while I went away for a week. Cathalina was great with my kitty Domino, who is moody and under the impression he’s a dog. She played with him even after he tried to get her at the start of one of their visits! Hero in my book lol great communication and lots of pics! Definitely will book her again for my next trip!”
“Heather was amazing to work with! She was a huge help walking our dogs while we were away for four weeks. My dogs loved her and she was so kind, taking such good care of both our active 5 year old Frenchie and our senior Frenchie and sending great pictures and updates along the way. She’s the best! ❤️”
Winchester dog parents share their Rover experiences
Sarah was wonderful with my pup Penny! Penny is used to pretty much always being by my side, and she was (unexpectedly) scared when I wasn't there. Sarah and her son took the time to coax Penny out from the under the bed and made her comfortable for future stop ins. As a pet parent, I felt much better knowing that my dog was both happier and in great hands! A very positive experience!
We truly cannot say enough good things about her. Grecia can sometimes be a bit bossy, and she did an amazing job reading her personality and understanding her needs. She was incredibly loving, attentive, responsible, and always punctual. She took wonderful care of Grecia, showed her so much affection, and made sure she felt comfortable and happy while we were away. We have no words to describe how amazing and incredible she was. We would not hesitate for a second to work with her again and highly recommend her.
Avery did an amazing job taking care of my dog, Ronin! I had some last-minute changes to my schedule, and she was incredibly accommodating. I get nervous leaving Ronin because he’s high-energy and takes medication, but my expectations were not just met — they were completely exceeded. Thank you so much for helping me feel at ease while I was away for the holidays, knowing my dog was safe and well cared for. I highly recommend Avery!!
MAX is our New Boston Terrier puppy, and as puppies are they need frequent meals and potty breaks. Lourdes did a fabulous job with Max's lunch and breaks . It was clear that Max loved being with Lourdes. She really came through to help us in a pinch. We got many pics /texts and he was in good hands!
We have been using Shawn for over 6 months for weekday drop-in visits with a very elderly dog. Shawn has been 100% reliable and a total pro the one time that the dog became very ill while home alone in the morning. Shawn invented a new outside game for our 13-yr-old pup, and now the dog wants to play the Shawn game anytime we are in the yard. We feel extremely fortunate to have found Shawn on Rover…she gives us total peace of mind that our wonderful dog is well-cared for. Shawn is completely trustworthy and totally dedicated to the well-being of our pet.
Popular requests near you
Select a filter and find qualifying Winchester sitters!How Rover works
1. Search
Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for dog sitting in Winchester is $25
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn't happen often, but if your dog sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Winchester average 6 repeat dog sitting clients
Dog Sitting FAQs
Frequently asked questions about Rover
Dog sitters on Rover are free to set their rates. The median cost to hire a dog sitter in Winchester on Rover as of Jun 2026 was about $25 per night, after factoring in Rover’s service fees. A dog sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.
As of Jun 2026, there are 10,555 dog sitters in Winchester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, 86% of Winchester dog sitters respond in under an hour.
Dog sitters in Winchester have an average of 14 years of experience. Dog sitters with repeat customers have an average of 6 repeat clients. Experience can vary from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Winchester.
Rover makes it easy to find Winchester dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:
- Dogs of all ages and abilities, including puppies
- Dog parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their dog sitter’s pets
There are 10,555 dog sitters in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 95% of dog sitters offer daily exercise, 95% offer medication administration, and 90% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass background checks for you and your dog’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.
Connect anywhere with the Rover app
