House Sitting in Winchester
Find a loving house sitter to watch over your pets and your home.
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Top rated Winchester house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Zoe did a wonderful job caring for my foster. She showed up on time and communicated with me throughout the day and even sent pictures putting my mind at ease. I felt very secure knowing my foster was being well cared for! I will definitely be using Zoe again!”
“I was very nervous about leaving my pets. Juliana was wonderful with them. From the meet and greet until I returned from my trip I had no worries. She sent me pictures everyday and I could see they were happy and loving her! I'd definitely have her care for my pets again!”
“Our 130# Newfoundland and cat were well taken care of. Communication was great, even using a different app since we were in Europe. Would not hesitate to use Charlotte again, she cared for our animals like they were hers.”
“Joshua was right on time and did an excellent job caring for and spending the night with our energetic 7 month old yellow lab puppy! Chessie just loved him! We definitely will have him back when the need arises!”
“Linda was a life-saver and took such great care of our pets and house so we could attend to a last minute family emergency. She did a fantastic job and we will definitely use her again in the future.”
About: I have had dogs my whole life and I have had a cat for the last 7 years. I am very good with animals and I love them very much. I have also babysat my own dogs when my parents go away as well as my aunts cats, and my neighbors dogs and cats. Since I've had many animals in my life, I know how to take care of them and I know how to tell what they need. I am in college but have many hours throughout the days that I am available and I am also free most nights (though I would need notice incase I make plans with friends) I am available all day on Mondays, available from 11-2 and after 5:30 on Tuesdays and Thursdays and available all day besides 2-4 on Wednesdays and Fridays. I am also available all day on weekends I would just need to know in advance due to plans. I will offer your pet lots of love and will do whatever is best for your pet! I can easily crate your dog and I love long walks and would be happy to go on one with your pet.
About: I have taken care of friend’s dogs for the past year! This has included cleaning up after them, walking and feeding them. I find joy in being able to look after and care for any dogs that might be in need of a friend! I am currently a college student that is starting Spring season! I am good for early mornings as well as visits during the day and night! I care for pets by maintaining their regular routines, including feeding, walks or potty breaks, playtime, and lots of attention. I follow all care instructions closely, prioritize safety, and provide updates with photos so owners feel confident their pets are in good hands.
About: I've been around dogs and cats since an early age, and quickly establish rapport with them. I've always taken good care of my pets, and will take good care of yours. I specialize in hour long visits, giving your dog time to exercise and relax. I can take them to the rec fields, to the river, or on hikes. I work remotely, and can fit pet care in when needed. I live near Old Town and can quickly reach properties in the surrounding area. Caring for an animal goes beyond filling a bowl or taking a walk. That's why I enjoy building rapport with animals, so they feel happy and safe.
“Julia is wonderful with our cat! We always know he is in good hands. When we come home, it's like we never left. Julia always keeps us up to date with photos and videos which is really nice when we're missing him. Thanks so much!”
“She was amazing! Came on time, follow all the instructions with my little puppy. Send me the updates and photos of Poet. Puppy was happy and safe when I came back home. Her prices are very affordable. You can feel that she loves the animals. Highly recommend Christopher!”
“Shannon was great with our dog for a 2 night house sitting. She was excellent with communication and gave us updates and pictures while we were gone. She left our home in great condition, and we would definitely use her again!”
“Kathy is a true gem. We had complete peace of mind while she house sat our three Lab rescues. Kathy is dependable, communicative, and takes care of your house and pets like they are her own. We will absolutely be booking her again.”
About: I’ve taken care of all dogs and cats for most of my life. I used to work at an animal shelter and absolutely adored it! I can do anything and everything you would like me to do! I can provide overnights, drop in’s, and dog walking throughout the day. I work 1pm-11pm Wed-Sat every week. I could come for overnights after I get off. I would much rather do a visit or overnight at your own home if that is any way possible as it would make the dog much more comfortable.
“Mary was wonderful! She took care of Pippa for a week! I will definitely be asking her back. She kept me posted with pictures and videos. When the power flickered and caused the AC to go out, she tried troubleshooting, and then dealt with the electrician and HVAC tech. I felt very good wirh Mary yaking care of that and Pippa too!”
“Alex was fantastic. Very knowledgeable about dog behavior and very diligent with sending us updates of our pups. She also took very good care of our house. We would definitely recommend Alex and plan to use her again.”
“Brent was great with our two dogs (65lbs, and 15lbs). He also took great care of our home. He sent lots of pictures and videos throughout the trip. We plan to hire him in the future.”
“Alyssa was an awesome sitter! My dog can be shy around new people and she did an amazing job getting my dog to warm up to her and she was excellent with sending updates and pictures! Will definitely use her again!!”
“Jennifer was a doll! She was so kind and caring. She even sent pics of our babies while we were on vacation and kept in touch with us. We can’t wait to call on her for next time!”
Over 484 pet parents in Winchester have booked house sitting
Winchester pet parents share their Rover experiences
Could not be more pleased with the compassionate care our dogs received while we were out of the country on vacation! I am the animal worrier of the family and felt very much at ease while away. We returned to a home of happy puppies! Thank you so very much for providing top notch care!
Julie is an excellent pet and house sitter. She’s very competent, reliable, and attentive, and we never had to worry about anything while we were away. Knowing our home and pets were in such good hands gave us real peace of mind. We would absolutely recommend her and happily use her again.
Mary was outstanding! She pet and house sat for me while I was out of the country for 10 days. Coming home to a clean, maintained house and my happy pup made my trip a success! Mary has great communication skills, very thorough & understanding. She met and exceeded my expectations. Job well done and appreciated! Thank you, Mary!
She was amazing! Came on time, follow all the instructions with my little puppy. Send me the updates and photos of Poet. Puppy was happy and safe when I came back home. Her prices are very affordable. You can feel that she loves the animals. Highly recommend Christopher!
Kathy G was awesome with our pups while we were gone. She sent updates, pictures and more every day which really kept us from worrying about our fur babies! She also left us a clean house and kept up on the dog items that needed washing. We will definitely call Kathy G again!
What an absolute Doll Tearia is… she did a fantastic job with our babies today… she put the thunder hood and thunder shirt on one of my Goldens during the storm. She was on time and the house was perfect when we got home. She left a lovely note and we will definitely be calling her in the future! Top notch!
Kim is an incredible human, and our first choice with who we will trust with our home and our pets while we are away. She is excellent at giving updates and sending pictures, she is on time, she is kind, trustworthy, and she clearly loves her work. Thank you, Kim!
Ashley did an outstanding job of taking care of our Pupper while we gone for the weekend. She gave detailed updates throughout those couple of days and sent us photos! I highly recommend her services if you need someone professional, responsible and will take of your pups like her own.
How Rover works
1. Search
Read verified reviews and choose a house 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 house and 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!
The median cost per night for house sitting in Winchester is $50
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 house 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.
Sitters in Winchester average 3 repeat house sitting clients
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Winchester on Rover as of Mar 2026 was about $50 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
As of Mar 2026, there are 316 house sitters in Winchester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 86% of Winchester house sitters respond in under an hour.
House sitters in Winchester have an average of 14 years of experience. House sitters with repeat customers have an average of 3 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Winchester.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Winchester house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house 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 house 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 house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.
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