Pet Sitting in Winchester
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
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Top rated Winchester pet sitters
“Thank you! My dogs were very happy when I got home , so I know that they were well cared for!”
About: With years of experience caring for pets, I offer reliable and compassionate service for your furry pet. I understand each pet has unique needs and I tailor my care to ensure they feel comfortable and loved. From daily walks to overnight stays, I provide personalized attention and a safe environment. You can trust me to give your pet the best care while you’re away. Your pet will feel right at home in my care! As a stay-at-home mom, pet care fits seamlessly into my daily routine. My flexible schedule allows me to provide personalized care for your pet, whether it’s walks, playtime, or feeding. My children and I enjoy spending time with animals, so we naturally incorporate pet care into our daily activities. I can ensure your pet receives plenty of attention, exercise, and love while also managing household responsibilities. Whether it’s daily check-ins or extended stays, I’m able to offer reliable, loving care that fits into my routine. In my home, I create a pet-friendly environment where pets and my children can interact safely. My kids are involved in daily walks, playtime, and feeding routines, ensuring pets receive plenty of attention and affection. I supervise all interactions to ensure a calm, positive experience for both pets and children. At your home, I maintain your pet’s routine, following your instructions carefully while offering companionship and care. My children are respectful of pets, and I make sure your pet feels safe and loved in any environment.
About: I am a vet tech have been in the field for 20 years I can do any medical situations if needed. Such as diabetic pets etc medications or injections needed. I work full time but I can work around my schedule. We can work it out upon seeing what is needed and what I can do for you and your babies I will not be having any in home pet care at this time. My place is not set up for visitors. Just let me know what is needed and I will see what I can do
About: I’ve taken care of dogs my whole life and always been around them! I have my own pup and am also a dog groomer by day! So I would be more than happy to care care of your pup in any way I can :) I’m currently full time, so Thursday and Fridays are my days available for boarding! We have lots of fenced in land for your dogs to play and have fun! I have a fenced in yard and a very playful pup that would love to play with yours! I can leash walk your dogs around if necessary and kennel if necessary as well!
“Dawn was so sweet and patient with my unhappy kitty and did a great job taking care of her while I was out of town. Highly recommend her to take care of your furry friend.”
About: I have cared for dogs since I was a kid and my babies are truly part of our family. We love all types of dogs and enjoy allowing our dogs to interact with new friends! I am an administrator in the local school district and we have an rarly start. During the week I am available in the evenings and on weekends I spend time at home with my husband, our two kids, and our pups. We have a fenced backyard and an open concept home inside. Because our kids are younger, we have two spare bedrooms that are able to house additional fur babies throughout the week in their own respective spaces.
“So glad I found Kristi and she was able to watch my babies on short notice! She is reliable, has excellent communication, and sent me cute pictures and updates every visit. Usually I don't sleep well and worry about my pets while out of town. This time I actually felt relaxed and didn't worry. I would definitely use Kristi again ?”
About: At age 16 I helped open up Homeland Pet hotel. I worked there 2 1/2 yrs. I was hooked. I have trained my dogs, my family and friends dogs and than helped with police K9s until I retired. I moved to Kentucky to work and be in an internship with a great training facility. In 2018 I moved back to California. I traveled and now I want to stay home and take care of or train your dogs. I take care and train all ages, size and breed of dogs. I have administered medications in all forms and I bath, brush and do nails. I am retired and I have the time and the means to help you and your pets have fun in life. I take my dogs to dog park and beach weekly when I am not camping. I am the person in my family everyone calls when they have a dog question. I am attentive, kind and playful, but I do have boundaries. I communicate very well with dogs and I'm pretty good with humans also. I have a 6 ft fence around my entire yard. I have my property sprayed for fleas and other critters every other month. It's a quarter acre property well maintained. I plenty of space inside for pets and I have several crates in all sizes if needed.
“Great service, quick to respond. Went above and beyond for me drop ins”
“Thank you so much! Love the pics!”
About: I have been a devoted pet caregiver and self owner since the age of 10. I have experience training and care giving for many different type of breeds such as huskies , poodles , jack Russell’s, German shepherds, pit bulls , and more. I always have experience with cats as well and love them just as much. My passion for the genuine care of animals is immense and I would strive to give the best service always. I have been fortunate enough to take some time away from my 9-5 and have had a dire need to pick up a hobby of something I genuinely would LOVE to do. My schedule is completely open to the needs of fur babies! I have one extremely friendly and loving husky who would love to engage with other pets just as much as I would. I have a large fenced backyard for play and gates that block off any potential hazards such as a open road.
“Amazing pet caregiver. Stayed and played with the dogs and followed feeding instructions to a tee. Provide numerous pics and great comments, I would highly recommend her!!”
“Heather was amazing! I’m always a little stressed out to leave my cat home alone but with the checkins and pictures Heather provided, I felt at ease. She went above and beyond to care for my cat while I was out of town. Definitely will rebook.”
About: I make sure to pay extra attention to the needs of dogs to make sure all dogs are well maintained and to make sure there feeling at met. Currently working full time job so sat and sun would be best day. And Friday would have to at 3:00. Thank you so much for your time. I have a fence if needed no grass of yet still working on that stage my dog loves to play with other dogs and he has all med tags up to date
“Honestly, I cannot say enough to do justice to how amazing Joanne is. She goes above and beyond. Our golden lab stayed with Joanne over the holidays while we were out of state and I knew immediately that she was being loved and cared for. Joanne sent frequent photos and videos of all the dog adventures they went on (hiking, bike rides, dog park) as well as sweet photos of them relaxing on the sofa and cuddling. Our dog had some social anxiety around other large dogs previously and Joanne even helped her through that, our dog had many dog friends by the end of her stay which I did not think was possible! I can tell our dog misses Joanne; she is authentic and her love for animals is evident in the care she provides. I am so grateful we have found her.”
“If I could give more than 5 I would. She took such great car, always sent pictures, and was timely in everything. This was our first drop in visit and she came to do a meet and greet to make sure we felt comfortable. Will absolutely use her in the future!”
“I have used Amy 3 times for drop-ins & definitely amazing with my pup ! Especially when it’s last minute, so thank you for that !”
About: I have 4 amazing dogs of my own and I have helped take care of pets for friends, family, and neighbors for as long as I can remember. I am experienced in senior care for dogs as I have my own senior dog who I take care of 24/7. I have volunteered at shelters and have also been a foster care mom for dogs in need of a home until their permanent home. Animals have always been my #1 priority. I work from home so my availability is pretty open. I make my own work schedule so it makes it easier in order for me to be available for pet parents who may need me. I have a fenced in backyard so your pets will have an area to roam around and let out their energy. I also have crates inside the house in case your pet needs to be created.
“Gizelle is punctual and took good care of my Teddy Bear & Lucy I would definitely recommend her!”
About: I’ve had my dogs all my life, from small dogs to big dogs, I love them all. My friends and family always count on me to help out with drop ins or dog walking. I’m currently in an externship for ultrasound and so this is part time for me which allows me to have extra time in the evenings during the week and the full day I have available on the weekends. I care for pets in my home and clients by playing with them and showing them love making sure their water is clean and making sure they get their exercise in!
Loving pet sitters in your neighborhood
The prices below are estimates per visit for 1 cat, including fees. Pricing may vary based on your search.
Search Results
1. Estela A.
“Thank you! My dogs were very happy when I got home , so I know that they were well cared for!”
2. Elsie R.
“I believe Elsie would be perfect for this position, In my personal experience Elsie has always taken care of her pets with the up most care. I believe she would treat any animal in her care as if it were her own.”
3. Bri P.
“I've known Bri since the Spring of 2020. She has always shown great care for and kindness to my fur babies. She also has provided me with emotional support during emergency situations. I always know that my four legged children are going to be well looked after, loved on, and a bit spoiled with her.”
4. Isabel C.
About: I’ve taken care of dogs my whole life and always been around them! I have my own pup and am also a dog groomer by day! So I would be more than happy to care care of your pup in any way I can :) I’m currently full time, so Thursday and Fridays are my days available for boarding! We have lots of fenced in land for your dogs to play and have fun! I have a fenced in yard and a very playful pup that would love to play with yours! I can leash walk your dogs around if necessary and kennel if necessary as well!
5. Dawn B.
“Dawn was so sweet and patient with my unhappy kitty and did a great job taking care of her while I was out of town. Highly recommend her to take care of your furry friend.”
6. Scheavonna L.
About: I have cared for dogs since I was a kid and my babies are truly part of our family. We love all types of dogs and enjoy allowing our dogs to interact with new friends! I am an administrator in the local school district and we have an rarly start. During the week I am available in the evenings and on weekends I spend time at home with my husband, our two kids, and our pups. We have a fenced backyard and an open concept home inside. Because our kids are younger, we have two spare bedrooms that are able to house additional fur babies throughout the week in their own respective spaces.
7. Kristy T.
“So glad I found Kristi and she was able to watch my babies on short notice! She is reliable, has excellent communication, and sent me cute pictures and updates every visit. Usually I don't sleep well and worry about my pets while out of town. This time I actually felt relaxed and didn't worry. I would definitely use Kristi again ?”
8. Tammi (Shigtastic) B.
“Tammi has a true passion for training and caring for dogs. Her and her 3 dogs are very welcoming. Our dog has a great time when he stays with them all; He starts whining with excitement as soon as we turn onto her street!”
9. Cecilia G.
“Great service, quick to respond. Went above and beyond for me drop ins”
10. Taylor G.
“Thank you so much! Love the pics!”
11. Keiona D.
“I have had the pleasure of watching Keiona work hand-in-hand with animals. I have seen the love and passion she gives when caring for her own Husky, Libiya. I have also visited multiple pet shelters with Keiona where she is overjoyed with the interactions she gets with puppies and older dogs alike. I believe Keionas caring, loving, and passionate personality makes her the perfect fit to care for anybody beloved animal.”
12. Jenny D.
“Amazing pet caregiver. Stayed and played with the dogs and followed feeding instructions to a tee. Provide numerous pics and great comments, I would highly recommend her!!”
13. Heather R.
“Heather was amazing! I’m always a little stressed out to leave my cat home alone but with the checkins and pictures Heather provided, I felt at ease. She went above and beyond to care for my cat while I was out of town. Definitely will rebook.”
14. Joseph H.
About: I make sure to pay extra attention to the needs of dogs to make sure all dogs are well maintained and to make sure there feeling at met. Currently working full time job so sat and sun would be best day. And Friday would have to at 3:00. Thank you so much for your time. I have a fence if needed no grass of yet still working on that stage my dog loves to play with other dogs and he has all med tags up to date
15. Joanne B.
“Honestly, I cannot say enough to do justice to how amazing Joanne is. She goes above and beyond. Our golden lab stayed with Joanne over the holidays while we were out of state and I knew immediately that she was being loved and cared for. Joanne sent frequent photos and videos of all the dog adventures they went on (hiking, bike rides, dog park) as well as sweet photos of them relaxing on the sofa and cuddling. Our dog had some social anxiety around other large dogs previously and Joanne even helped her through that, our dog had many dog friends by the end of her stay which I did not think was possible! I can tell our dog misses Joanne; she is authentic and her love for animals is evident in the care she provides. I am so grateful we have found her.”
16. Lindsey V.
“If I could give more than 5 I would. She took such great car, always sent pictures, and was timely in everything. This was our first drop in visit and she came to do a meet and greet to make sure we felt comfortable. Will absolutely use her in the future!”
17. Amy M.
“I have used Amy 3 times for drop-ins & definitely amazing with my pup ! Especially when it’s last minute, so thank you for that !”
18. Brittany C.
“Brittany is absolutely amazing with pets and would make the perfect Rover walker! She truly loves animals and goes above and beyond to ensure they are happy, safe, and cared for. Whether it’s giving extra cuddles, making sure they get their favorite treats, or paying attention to every detail of their needs, Brittany is the kind of person every pet owner dreams of trusting with their furry family members. I couldn’t recommend her more!”
19. Gizelle L.
“Gizelle is punctual and took good care of my Teddy Bear & Lucy I would definitely recommend her!”
20. Rosalinda C.
“I was out for a week and needed a dog handler and Rosalinda was more than happy to take care of my dog for that week providing great playtime and walks, when I got back my dog looked healthy and well taken care of I would definitely recommend her or leave my dog Shiloh with her again.”
How Rover works
1. Search
Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets 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!
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 pet sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Pet Sitting FAQs
Frequently asked questions about Rover
Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Winchester on Rover as of May 2025 was about $25 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.
As of May 2025, there are 316 pet sitters in Winchester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 87% of Winchester pet sitters respond in under an hour.
Pet sitters in Winchester have an average of 15 years of experience. Pet sitters with repeat customers have an average of 6 repeat clients. Experience can vary from pet sitter to pet 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 pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
There are 316 pet sitters in Winchester on Rover, so you’re sure to find the perfect match for your pet! In Winchester, 100% of pet sitters offer daily exercise, 94% offer medication administration, and 94% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass background checks for you and your pet’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
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