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.

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Sitter Profile Image: Lawton B.
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Lawton B.
Star Sitter
from
$35
per night
5.0 out of 5 stars
15 reviews
7 repeat clients
10 years of experience
Ballwin, MO, 63011

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

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Brenda M.
Sitter Profile Image: Alexandria B.
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Alexandria B.
from
$40
per night
4.9 out of 5 stars
18 reviews
4 repeat clients
18 years of experience
Town and Country, MO, 63017

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!

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Jasmina H.
Sitter Profile Image: Evelyn W.
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Evelyn W.
from
$40
per night
5.0 out of 5 stars
4 reviews
1 year of experience
Ballwin, MO, 63021

Evelyn was very polite and great with our dog! Would recommend!!

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Nicole L.
Sitter Profile Image: Kelsey R.
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Kelsey R.
from
$40
per night
5.0 out of 5 stars
4 reviews
10 years of experience
Ballwin, MO, 63021

Kelsey took amazing care of our pups, did a great job communicating and went above and beyond. We will definitely book her in the future!

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Tracy B.
Sitter Profile Image: Cynthia S.
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Cynthia S.
Star Sitter
from
$55
per night
5.0 out of 5 stars
60 reviews
24 repeat clients
30 years of experience
Ballwin, MO, 63021

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!

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Lindsay M.
Sitter Profile Image: Alex F.
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Alex F.
Star Sitter
from
$60
per night
5.0 out of 5 stars
147 reviews
46 repeat clients
25 years of experience
St. Louis, MO, 63131

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.

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Charlotte B.
Sitter Profile Image: Kate M.
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Kate M.
from
$50
per night
4.9 out of 5 stars
12 reviews
3 repeat clients
20 years of experience
Ballwin, MO, 63011

I had complete confidence in Kate since our first meet and greet with the pups. She took her time to earn their trust and the whole pack agreed she was the one.

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Amee V.
Sitter Profile Image: Ava & Eve B.
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Ava & Eve B.
from
$50
per night
5.0 out of 5 stars
6 reviews
1 repeat client
30 years of experience
Wildwood, MO, 63040

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.

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Angie S.
Sitter Profile Image: Ashley W.
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Ashley W.
from
$40
per night
5.0 out of 5 stars
6 reviews
3 repeat clients
12 years of experience
Shaw, Ballwin, MO, 63021

Did a great job, very nice.

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Adam A.
Sitter Profile Image: Thomas H.
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Thomas H.
from
$80
per night
5.0 out of 5 stars
8 reviews
3 repeat clients
50 years of experience
Ballwin, MO, 63011

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.

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Jane S.
Sitter Profile Image: Emily & Emily S.
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Emily & Emily S.
from
$56
per night
18 years of experience
Ballwin, MO, 63021

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.

Sitter Profile Image: Jeremy W.
Verified Enhanced Background Check
Jeremy W.
from
$45
per night
5.0 out of 5 stars
42 reviews
18 repeat clients
15 years of experience
Des Peres, MO, 63131

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.

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David B.
Sitter Profile Image: Alisa G.
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Alisa G.
from
$60
per night
5.0 out of 5 stars
17 reviews
5 repeat clients
15 years of experience
Ballwin, MO, 63021

Alisa was able to help lucky last minute and we are very appreciative. Thank you for taking such good care of him and sending pics.

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Megan D.
Sitter Profile Image: Zoe S.
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Zoe S.
from
$25
per night
5.0 out of 5 stars
2 reviews
14 years of experience
Ballwin, MO, 63021

Dogs were happy and the house was in good shape.

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Peggy J.
Sitter Profile Image: ROSEMARY B.
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ROSEMARY B.
from
$44
per night
5.0 out of 5 stars
11 reviews
1 repeat client
30 years of experience
Ballwin, MO, 63011

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!

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Clint M.
Sitter Profile Image: Ryan H.
Verified Background Check
Ryan H.
Star Sitter
from
$25
per night
5.0 out of 5 stars
69 reviews
15 repeat clients
11 years of experience
Fenton, MO, 63026

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!

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Jonathan W.
Sitter Profile Image: Carter Z.
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Carter Z.
from
$35
per night
5.0 out of 5 stars
1 review
1 year of experience
Eureka, MO, 63025

Communicated well and took great care of lucky and put home

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Megan D.
Sitter Profile Image: Lesley S.
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Lesley S.
from
$55
per night
5.0 out of 5 stars
23 reviews
6 repeat clients
20 years of experience
Des Peres, MO, 63131

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!

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Sarah Q.
Sitter Profile Image: Samantha S.
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Samantha S.
Star Sitter
from
$38
per night
5.0 out of 5 stars
18 reviews
3 repeat clients
10 years of experience
Fenton, MO, 63026

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.

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Emily W.
Sitter Profile Image: Bennett H.
Verified Enhanced Background Check
Bennett H.
from
$45
per night
5.0 out of 5 stars
29 reviews
6 repeat clients
16 years of experience
Kirkwood, MO, 63122

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.

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Anne V.
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Winchester pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

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 :)

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Vassil P.
House Sitting
5.0 out of 5 stars

Cindy is a gem! She was so sweet and sent so many updates of our pup! We felt comfortable having her stay with our fur baby as soon as we met her. So glad we found her and will definitely be reaching out again!

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Britney M.
House Sitting
5.0 out of 5 stars

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!

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Alyssa B.
House Sitting
5.0 out of 5 stars

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.

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David B.
House Sitting
5.0 out of 5 stars

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!

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Michael J.
House Sitting
5.0 out of 5 stars

Abigail goes above and beyond when taking care of Django. She is amazing. Definitely will use her again. I know Django is safe and loved.

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Tony S.
House Sitting
5.0 out of 5 stars

Alex was amazing. She took care of our dog and cat, both can by a little challenging, and did everything we asked. We would definitely recommend her to anyone needing care for their pets.

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David H.
House Sitting
5.0 out of 5 stars

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.

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Jane S.
House Sitting
5.0 out of 5 stars

Mark is absokutely Great with the dogs. Always provides the best care and leaves the house better than we did. 😀 highly recommend!!

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Shaun M.
House Sitting
5.0 out of 5 stars

Ava is always our go-to person for trusting to watch our pups and home! She uses good judgment and cares for our pets as well as for our home needs.

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Gretchen F.
House Sitting
5.0 out of 5 stars

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!

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JP J.
House Sitting
5.0 out of 5 stars

She was great! She kept me updated all night with lots of pictures. She made sure to give Winston a lot of attention and I could tell he really enjoyed his time with her.

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Kylie M.
House Sitting
5.0 out of 5 stars

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!

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Ev B.
House Sitting
5.0 out of 5 stars

Gabrielle did a fantastic job! My dogs were well cared for. I could tell from the intial meet and greet that she would be a great fit and my dogs would love. I can’t wait to book with Gabrielle again!

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Karyn T.
House Sitting
5.0 out of 5 stars

Kelsey took amazing care of our pups, did a great job communicating and went above and beyond. We will definitely book her in the future!

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Tracy B.
House Sitting
5.0 out of 5 stars

Rosemary was fabulous as a sitter for our pup!! She did all the dog stuff and even helped with package delivery and plant watering!! Very sweet person and cared for the house superbly too.

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Don A.
House Sitting
5.0 out of 5 stars

Lori took great care of our two dogs (and multiple other household tasks). She was a great communicator, very concerned about the dogs well-being, and gave us daily updates and pics. Highly recommended!

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Katie B.
House Sitting
5.0 out of 5 stars

Dogs were happy didn’t seem depressed. Grace took great care of our boys and updated us on how they were doing. Would definitely ask for Grace again and recommend to others. Thank you Grace!

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Randy & Cathy S.
House Sitting
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How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 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. 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.

If you’re searching for a Winchester house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

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.