Dog Sitting in Winchester
Book a Winchester dog sitter to watch your dog in your sitter’s home or yours.

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Top rated Winchester dog sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

“Gabby took excellent care of our animals while we had to go out of state. I could tell from her pictures and from how they were acting when we got home that they really enjoyed their time with her. We'd absolutely book Gabby again in the future!”


“This was our first time using Meghan with our pups while we were on vacation and they loved her! She was responsive, caring, and always sharing photos of how they were doing. I highly recommend her and we will definitely use her again soon!”


About: I love the joy that dogs add to life and I’m thankful to have the experience in raising and loving on so many! Loving your pet as if it were my own would be priority. I know it can be stressful in finding good help that you can count on so that would be my promise to you. Message me for more details or questions! After recently losing my own dog, I realize a majority of my daily routine involved and was centered around his care. I miss the responsibility and adventures! I would care for your pet in the same way you care for them to reduce stress in environmental change. Love and attention would be what your pet experiences under my care.

About: I cared for my family dog for 12 years until she passed, as well as cared for my family and friends furry animals over the years. I’m currently working full time. Can be available before 10:00-11:00 am and in evening after 6:30pm or 7:30pm. Work schedule rotates, and can be flexible. I’ll make sure they are safe at all times, and well taken care of. Take them on walks, feed them if needed, and play of course!

“Bridgette is amazing! I felt like our little pups were in safe hands and well taken care while we were away. We will definitely be reaching out to her again when needed. HIGHLY RECOMMEND!”


About: I grew up in a pet loving household with a German shepherd mix husky, a blue heeler, and even a dachshund mix basset hound. I’m comfortable with all sizes of dogs. I’m here to give your pup a quick and fun bathroom break (: I’m currently waiting to start a full time job at the beginning of September and have open availability until starting a new role. However I’m hoping to continue rover afterwards where it fits in my schedule. With owning my own dogs, I’ve had my fair share of collar slip outs. I always make for appropriate tightness of collars or harnesses and make sure the dog is comfortable with me prior to leaving the home.

About: Hey there my name is Allison and I am a huge animal lover! I will love on your fur babies while you are gone and make sure they have what they need! As someone that has every pet but a dog of her own and has always wanted one, I will completely take advantage of the time I get with yours! I am comfortable with whatever is in need feeding, walks, backyard play, even just hanging out at the house and keeping your animal company! I have experience with a wide range of animals and I will make sure your needs are met! I am so excited and looking forward to meeting you and your sweet fur baby! Whatever animal comes my way I will make sure they are taken care of!

“We had a family emergency and had to leave our Dog Piff at home and Shaghayegh was amazing! She really went above and beyond for my family and made sure our dog was taken care off. She let us know before and after she left and always sent pictures everyday! I would 100% use her again!”


“This was our first experience with Rover and it went very well. We were a little unsure of the process but it turned out pretty easy. We used Alex for drop in visits since we had to take our oldest back to school. He provided us with pictures and good feedback. It was important to us to have someone close and that had a love of animals. We would recommend Alex and will definitely be using his services again.”


About: I have been caring for friends and neighbors dogs, cats, and small animals since i was 13. I also volunteer at the PWC Animal Shelter! I am an incoming first year college student starting at Shenandoah University in the fall, i currently have a lot of availability all day, every day! I have a clean house and a large dog crate if you would like me to crate your dog, i have a friendly golden retreiver and two cats who are all great with other animals.

“Christa was excellent! She took my last minute booking and was really flexible with my schedule. She took tons of pictures and kept me updated on everything!! I would definitely recommend her to anyone and I will definitely be a repeat!!”


About: I love both cats and dogs and have had them my whole life! Today, I have a 4-year-old Shiba Inu that I rescued. I was given a Tuxedo cat for my fourth birthday and we got a Husky mix when I was around 10. I fed them and walked and played with them my whole childhood. When I was in college, I started fostering animals— both cats and dogs— for years on end. Some of the animals needed eye drops and oral medication which I helped administer. I even helped my mom adopt one of the cats I fostered! I promise to love and care for your pets as if they are my own! I work remotely from 2-10pm on Tuesdays-Saturdays! I’m best fit for mid-day, morning or late night walks and I am free for all-day/ overnight care on Sundays and Mondays. If I am able to work remotely from your house, I could also potentially work weekdays and weekday night. I can play with your pet and take your dog on long walks! I also have treats and toys at my disposal that I can share (per permission from the owner of course!)

About: I have taken care of Guinea pigs, cats, dogs, fish etc. I have worked with many different breeds and species of animals and an more than willing to learn something new. I have autoimmune disease so I don’t work a typical 9-5. But! That means I have more time to take care of your sweet little fur-babies! 😊 I will make sure your pup feels safe and loved while your are away. I can also check your mail and do some light house cleaning!

About: Hi my name is Jose Alfredo and I can be very laid back and socially outgoing with a fun and friendly personality! I love being around friendly pets and I was a previous cat owner for 4 years. I also share my place with my roommate and his dog of 3 years who I also help care for at times. I have other families who have pets as well and I have been around them long enough to love and know me. I have spent a lot of time around other people's dogs most of my life and have great experience with cats. Being around other people's pets over time has given me the opportunity to know and understand different dog and cat personalities and each ones individually unique needs and traits. Book me and I will walk your dog, feed it, play with it and make sure it has gone to the bathroom. I will tend to your cats' need as well and make sure it's fed, hydrated and help maintain it's litterbox's cleaniliness and given lots of attention! I am also willing to help with small house chores like taking out the trash, bringing the bin to the front, watering your plants or any other simple house duties for no extra charge! At the moment I will go to you to take care of your pet in your home so you don't have to worry about putting your pet in a new environment it's not used to. I will make sure everything in your home is as tidy as before I even arrived. As long as you can provide me with the proper details and instructions about your pets' needs, where things are and how to get in and out of the house, then I promise you everything will be done as requested. As a way of building trust, we will arrange to do a proper meet and greet at your home or a public place like the park. This is so me and your pet can get familiar with each other, earn trust between owner and sitter, and have comfortability and assurance that your pet and home will be in good hands. Thank you for choosing me to care for your pets! I am currently flexible with availability for most days of the week as I do not have any other full time job at the moment. However, I currently am a student studying full-time and sometimes get involved in campus events, extracurriculars, and other student organizations. As long as the requested time works around my schedule then we can make it work! During the spring time I have a class Monday mornings 9:20 - 10:10 AM. Then I have an afternoon class Tuesdays and Thursdays from 1:20 - 2:35 PM. Besides that I can be available before or after those times and whenever I am not spending time on campus. I do prefer to be notified at least 5 days in advance for requests but I am also willing to take up to same day bookings as long as I am completely free for that day. But please do try to reach out and book with me in advance at first if you can. I also prefer to schedule a meet and greet prior to accepting booking requests for new first time clients. But I will be more than happy to work with you so I can make a new furry friend! I play with my roommate's dog every day and feed him or take him outside to potty when the roommate is not around or unable to. I play ball with his dog, tug of war and give him belly rubs. His dog is also very attached to me as I am to him. I hope to form this same kind of relationship with your pet!

“Isabella we as BEST! She communicated from the start and we were able to work out the best schedule. She sent cute pictures and videos of my girls (two cats) every time she visited and kept me up to date on their shenanigans. The girls are happy and healthy. Couldn’t have asked for a better sitter!”

Loving dog sitters in your neighborhood
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Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.


Gabby T.Star Sitter

“Gabby took excellent care of our animals while we had to go out of state. I could tell from her pictures and from how they were acting when we got home that they really enjoyed their time with her. We'd absolutely book Gabby again in the future!”


Meghan H.

“This was our first time using Meghan with our pups while we were on vacation and they loved her! She was responsive, caring, and always sharing photos of how they were doing. I highly recommend her and we will definitely use her again soon!”


Alexandria Y.

“Alexandria is great. She is awesome with our dog.”


Joanna S.
About: I love the joy that dogs add to life and I’m thankful to have the experience in raising and loving on so many! Loving your pet as if it were my own would be priority. I know it can be stressful in finding good help that you can count on so that would be my promise to you. Message me for more details or questions! After recently losing my own dog, I realize a majority of my daily routine involved and was centered around his care. I miss the responsibility and adventures! I would care for your pet in the same way you care for them to reduce stress in environmental change. Love and attention would be what your pet experiences under my care.


Courteney B.
“Love love love her! She kept me updated as we were traveling, always sending pictures and giving very detailed updates on their eating/playing/potty trips, etc. She is always available and flexible and understanding that sometimes plans change! Highly recommend Courteney to anyone needing someone trustworthy to look after their fur babies.”


Bridgette M.

“Bridgette is amazing! I felt like our little pups were in safe hands and well taken care while we were away. We will definitely be reaching out to her again when needed. HIGHLY RECOMMEND!”


Sophia P.
“I can’t say enough great things about Sophia! She is simply amazing in the pet care she gives to my dog, Scout. Her every day standards go above and beyond simply feeding and walking my pup. She is like family to us and I never have to worry about my dog when I leave him in Sophia’s care.”


Steven F.

“Steven showed up on time and even cleaned up a bit of a mess my dogs had made! Will definitely book again when I need a drop in!”


Allison B.
“Allison is very dependable, never calls out or leaves you hanging for a commitment. Allison shows respect to peers, adults and customers. Allison would be perfect for this position with Rovers due to her love of animals. Allison's smile is infectious. Thank you, Janet Miller Marketing Manager Atomic Trampoline Park”


Shaghayegh H.
Star Sitter


“We had a family emergency and had to leave our Dog Piff at home and Shaghayegh was amazing! She really went above and beyond for my family and made sure our dog was taken care off. She let us know before and after she left and always sent pictures everyday! I would 100% use her again!”


Karen & Kyle W.

“Karen does an amazing job with my cat Heidi! Highly recommend. She’s responsive and loves cats and animals. She takes care of my cat like she’s her own.”


Hannah U.

“I love seeing the pictures of my dear kitties when I'm gone. And Hannah was friendly and helpful about taking care of everything in my absence.”


Alex H.

“This was our first experience with Rover and it went very well. We were a little unsure of the process but it turned out pretty easy. We used Alex for drop in visits since we had to take our oldest back to school. He provided us with pictures and good feedback. It was important to us to have someone close and that had a love of animals. We would recommend Alex and will definitely be using his services again.”


charlotte g.
About: I have been caring for friends and neighbors dogs, cats, and small animals since i was 13. I also volunteer at the PWC Animal Shelter! I am an incoming first year college student starting at Shenandoah University in the fall, i currently have a lot of availability all day, every day! I have a clean house and a large dog crate if you would like me to crate your dog, i have a friendly golden retreiver and two cats who are all great with other animals.


Christa K.

“Christa was excellent! She took my last minute booking and was really flexible with my schedule. She took tons of pictures and kept me updated on everything!! I would definitely recommend her to anyone and I will definitely be a repeat!!”


Sophia C.
About: I love both cats and dogs and have had them my whole life! Today, I have a 4-year-old Shiba Inu that I rescued. I was given a Tuxedo cat for my fourth birthday and we got a Husky mix when I was around 10. I fed them and walked and played with them my whole childhood. When I was in college, I started fostering animals— both cats and dogs— for years on end. Some of the animals needed eye drops and oral medication which I helped administer. I even helped my mom adopt one of the cats I fostered! I promise to love and care for your pets as if they are my own! I work remotely from 2-10pm on Tuesdays-Saturdays! I’m best fit for mid-day, morning or late night walks and I am free for all-day/ overnight care on Sundays and Mondays. If I am able to work remotely from your house, I could also potentially work weekdays and weekday night. I can play with your pet and take your dog on long walks! I also have treats and toys at my disposal that I can share (per permission from the owner of course!)


Mary M.
“Mary is amazing with animals!! She loves them. She has a dog of her own that she takes extremely good care of. My Ashton (who takes to nobody) took immediately to Mary. She’s the only one he’ll let pick him up and carry him. She’s patient, loving, knows an animal’s specific queues, is a great trainer, and I’d recommend her a thousand times over to watch your babies! She’s always on time and she always - ALWAYS makes time if I need her on the fly.”


Jose O.
“Jose is a responsible and caring person and especially when it comes to animals. He takes great care of his own cat that he has had for more than two years, but also has taken care of my own. When I got hit with Covid he took the initiative of cleaning the litter box, making sure he had food, and played with him. Alfredo has a great personality and has the perfect energy for pets!”


Alyssa F.

“Alyssa is so amazing with the pups, and I'm very grateful for her professionalism.”


Isabella M.

“Isabella we as BEST! She communicated from the start and we were able to work out the best schedule. She sent cute pictures and videos of my girls (two cats) every time she visited and kept me up to date on their shenanigans. The girls are happy and healthy. Couldn’t have asked for a better sitter!”
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 dogs2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
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.
Dog Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, dog sitters on Rover respond in under an hour.
Experience can vary widely from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when comparing dog sitters available 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
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.
