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.
“Lawton did a fantastic job watching our dogs. They were happy when we returned and well taken care of. She took them on numerous walks/hikes, played fetch in the yard, and gave our elderly dog extra attention. She took great care of our home as well. She sent daily updates as well Would highly recommend her and plan to use her again”

“Alexandria was a phenomenal pet sitter! We felt completely at ease and were able to fully enjoy our trip knowing our animals were in such good hands. She cared for them as if they were her own—attentive, playful, and always keeping our dog company. It’s clear our pets love her and feel comfortable around her. We’ll absolutely hire her again for any future travel!”

“We were so lucky to find Cynthia!! This was our first time using Rover and we were nervous to ask a stranger to watch our 4 dogs for 10 days, but Cynthia couldn’t have put us more at ease 😊. She sent frequent updates, is a great communicator, and is a sincere caretaker - taking the time to get to know each dog and caring for their individual needs. Cynthia is HIGHLY recommended and GREATLY appreciated!”

“Wonderful experience having Alex and Christine house sit and take care of our little dog. They did a great job, sent messages every day and pictures knowing that we missed our sweet companion. Highly recommend them, you will not be sorry.”

“Ava was a lifesaver and a great sitter for my two pups. I had a dog sitter cancel and she stepped in at the last minute. She was very responsive and sent updates often. I will definitely ask her to sit with my pups again.”

“Thomas was professional and provided excellent care from the first message to his time spent with Owen. It was not your standard "house sitting" since he did not have to stay overnight but provided the help needed while I was away for the day. He came to meet us first so he could learn more about Owen and the things to make their time together go smoothly. Owen had a great time with Thomas playing outside at his house and then was able to get him home safely to sleep in his own bed. I appreciate the care Thomas provided and was so helpful to ensure Owen was comfortable with him. I look forward to having him watch Owen next time.”

About: I typically bring my partner, Eshap. We are both cat and dog lovers! A bit more about us below :) Emily - Cat lover! Grew up with cats and i'm currently still taking care of my babies Dusty and Cloudy (brother and sister) who are almost 18 years old. Dusty has medical issues so I'm comfortable with administering medication if need be. Ive also house and cat sat for several friends and am very familiar with the way kitties like to play, sleep, eat, and interact with humans. Have dog sat for about 8 different clients, and some friends and enjoy taking care of dogs too :) Eshap - I grew up with a total of 4 dogs over the years. I love them all dearly! One loving and loud beagle, one mutt, one sweet and chill dachshund, and one very high-energy silver lab and pitbull mix. Have dealt with puppies all the way to very senior dogs. I love cats and have lived with many over the years with roommates. I have pet sat both dogs and cats over the years, making sure they are loved, played with, fed, and walked. As for house sitting, I am clean and tidy, and am a lover of plants. I will be the one keeping your plants alive and thriving! I have around 15 of my own. Having two peoples schedules allows us to spend more time with your pets! We both work part time, so someone is typically home with them or taking the dog on an adventure :) We follow all guidelines that are given by the pet parent about security, rules of the home, pet care, and whatever else may be requested.
“Wow! This was our first experience with Rover and we were very fortunate to find Jeremy. Everything about the experience was first class. I highly recommend Jeremy, but I selfishly do so with caution. Everyone will want to hire him and he won’t be available for us next time. Definitely a 5 star experience. Jeremy was prompt, communicative, respectful, attentive to our requests, also to the animals, and flexible in his schedule. Thank you Jeremy.”

“Great sitter. Rosemary sent photos and communicated frequently. Most importantly, she seemed to truly enjoy working with Sydney. Our dog can be a little difficult sometimes and we often come back to a dehydrated, depressed pup. She seemed to be in great spirits and that’s a credit to Rosemary. Would definitely recommend!”


“First time using Rover to find a reliable person to house sit my pups. I’m so thankful for Ryan and this app! She spent time with me before our trip to learn about my pups and their daily routines. We came home to our surprise that Ryan stayed until we got home and talked to us about the pups adventures:). She stayed in contact with me during our trip and kept us informed about them. She was also easy to get ahold of. She is a warm and kind soul and truly cared for our pups. Will definitely ask her again in the future to watch our pups!”

“Lesley was a life saver! We have 2 dogs, a cat, 2 mini donkeys, and a horse and she cared for all of them while we were gone. She even sent pictures of our babies which I love receiving while away from them. She gave them lots of cuddles and love; even if the cat may have forced her to cuddle more than anticipated 😅 we will definitely be reaching out to Lesley again whenever we need someone we can trust to watch our four legged babies!”


“Total peace of mind! It’s hard to find someone you trust with your home and your pets, but Samantha exceeded all expectations. Our dogs were happy and calm when we returned.”


“Bennett did a wonderful job watching my two dogs while my family was on vacation. He bonded with both of them and helped them be comfortable while we were gone. I will definitely ask Bennett to watch my dogs again.”

Winchester pet parents share their Rover experiences
We highly recommend Lawton. She was great with our almost-human :) family member! We received daily updates and photos from her stay with our dog. Moreover, Lawton went beyond just keeping an eye on him and our home - she watered our vegetable garden and set up wire fencing to protect it from the neighborhood squirrels and bunnies without any of this had been specifically asked by us. Thank you, Lawton - you are hired again :)

Lindsey was great with our dog! He can be a little shy and takes some time to warm up, but she was super patient and made him feel comfortable. She kept us updated, took great care of him, and we could tell he was in good hands. We really appreciated how kind and attentive she was, and we’d definitely trust her to watch him again!

Wow! This was our first experience with Rover and we were very fortunate to find Jeremy. Everything about the experience was first class. I highly recommend Jeremy, but I selfishly do so with caution. Everyone will want to hire him and he won’t be available for us next time. Definitely a 5 star experience. Jeremy was prompt, communicative, respectful, attentive to our requests, also to the animals, and flexible in his schedule. Thank you Jeremy.

Tarah did an outstanding job house and dog sitting for us while we were away. From the start, she was dependable, communicative, and clearly cared about making sure everything was taken care of. Most importantly, Jupiter and Elbert were happy, relaxed, and well cared for when we returned home, which says everything. It gave us real peace of mind knowing they were in such good hands. The house was also spotless and well looked after. We truly appreciated Tarah’s kindness, responsibility, and attention to detail, and we would absolutely trust her again in the future. Highly recommend!

Thomas was professional and provided excellent care from the first message to his time spent with Owen. It was not your standard "house sitting" since he did not have to stay overnight but provided the help needed while I was away for the day. He came to meet us first so he could learn more about Owen and the things to make their time together go smoothly. Owen had a great time with Thomas playing outside at his house and then was able to get him home safely to sleep in his own bed. I appreciate the care Thomas provided and was so helpful to ensure Owen was comfortable with him. I look forward to having him watch Owen next time.

Shruti was absolutely wonderful! She took excellent care of my dog and made me feel completely at ease while I was away. She sent frequent updates, photos, and videos, which I really appreciated- it was clear my dog was happy, comfortable, and having a great time. I highly recommend her to anyone looking for a trustworthy and loving caregiver for their pet!

Isabelle did a wonderful job staying with Lily for 6 nights recently. She was sweet, caring and made our time away less stressful. She asked questions if she had any and left our house just as she had found it. We appreciated her caring for Lilly and the photos and text messages. I highly recommend Isabelle and will use her again! Thanks Isabelle for doing such a fabulous job!

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 $49
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 4 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 Jun 2026 was about $49 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 Jun 2026, there are 1,459 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, 90% of Winchester house sitters respond in under an hour.
House sitters in Winchester have an average of 16 years of experience. House sitters with repeat customers have an average of 4 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.













