House Sitting in Winchester

Find a loving house sitter to watch over your pets and your home.

End
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

Top rated Winchester house sitters

Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

1 / 1
Sitter Profile Image: Eve Marie B.
Verified Enhanced Background Check
Eve Marie B.
$98
total per night
5.0 out of 5 stars
17 reviews
4 repeat clients
5 years of experience
Winchester, CA, 92596

Eve is so lovely! Such a nice human and really cared about our bulldog babies, which is all we could ask for while being out of town. She was very attentive towards them, gave them cuddles/attention and stuck to their strict schedule, which has kept them very happy pups. Thank you so much, Eve, and look forward to having you watch them again in the near future!

Profile image
Maeg D.
Sitter Profile Image: Donna L.
Verified Enhanced Background Check
Donna L.
$70
total per night
45 years of experience
Menifee, CA, 92584

About: I’ve been caring for dogs since I was a kid, from bottle-feeding little pups to looking after senior dogs who need extra love and support. I’m experienced with all ages and happy to give your dog the care they need. I currently work remotely part-time for an animal rescue in Brooklyn, which gives me a flexible schedule and plenty of time to focus on your pet’s needs. Pet care easily fits into my daily routine, and I’m available to watch your furry family member most days of the week When I’m caring for your pet in your home, I stick to the routine they know—meals, walks, playtime, and all the little things that make them feel comfortable. I treat your space with respect and make sure your furry friend gets tons of attention, company, and love while you’re away. I’ll send plenty of updates and cute photos so you never have to wonder how they’re doing.

Sitter Profile Image: Darian P.
Verified Enhanced Background Check
Darian P.
$68
total per night
5.0 out of 5 stars
3 reviews
1 repeat client
45 years of experience
Menifee, CA, 92585

My 3 dogs loved Darian! They were so glad they did not have to stay at a kennel or at home alone and that he was there at night. Darian also picked up the mail and took them for walks and gave one dog medication. I would love to have him come back and stay again!

Profile image
Patricia R.
Sitter Profile Image: Kristen C.
Verified Enhanced Background Check
Kristen C.
$70
total per night
5.0 out of 5 stars
57 reviews
25 repeat clients
9 years of experience
Winchester, CA, 92596

Kristin is fantastic. This is the second time we've had Kristen stay with our two beagles and we feel so comfortable knowing that she is taking care of them. She does a great job of communicating and sending photos often so we know all is good back home. Priceless.

Profile image
Jennifer S.
Sitter Profile Image: Havana P.
Verified Enhanced Background Check
Havana P.
$43
total per night
5.0 out of 5 stars
5 reviews
1 repeat client
21 years of experience
hemet, CA, 92545

Havana is incredibly reliable, loves pets, and is just an all around thoughtful, caring person! We trust her completely with our fur baby and we are so grateful to have found her.

Profile image
Christina V.
Sitter Profile Image: Melinda F.
Verified Enhanced Background Check
Melinda F.
$56
total per night
5.0 out of 5 stars
29 reviews
12 repeat clients
10 years of experience
Hemet, CA, 92545

Melinda is a true gem! She helped me out last minute and was so courteous and respectful of my fur kids. She went above and beyond to make sure I felt they were taken care of. Would I use her again? I have used this service a lot and she is the one who will stand out as the best that i have ever had. So friendly, so willing to help, super respectful, and just a cool person to boot. I would highly recommend her to anyone.

Profile image
Susan B.
Sitter Profile Image: Maria Amparo A.
Verified Enhanced Background Check
Maria Amparo A.
$88
total per night
5.0 out of 5 stars
39 reviews
9 repeat clients
30 years of experience
Canyon Lake, CA, 92587

I was anxious about leaving my dog for a week long trip until I saw how excited she was when Maria arrived at our house. I was truly able to relax and enjoy my trip knowing my pup was being spoiled with play and attention. Maria is friendly and professional and provided me with daily updates and photos so I could see my dog was being well cared for. I highly recommend Maria, especially for dogs/pet parents who didn't have good experiences at boarding facilities.

Profile image
Nikole C.
Sitter Profile Image: Shekina E.
Verified Enhanced Background Check
Shekina E.
$56
total per night
5.0 out of 5 stars
6 reviews
2 repeat clients
16 years of experience
Menifee, CA, 92584

Shekina did a great job with our three dogs and three cats. We came back to happy animals and a clean home. Will definitely use her again and highly recommend!

Profile image
Kelsea N.
Sitter Profile Image: Sierra R.
Verified Enhanced Background Check
Sierra R.
$43
total per night
5.0 out of 5 stars
8 reviews
15 years of experience
Winchester, CA, 92596

Sierra was great!!! I really appreciate the care she provided my pup. She was on time and communicated throughout the day. I will definetly request her again!!

Profile image
Tammy V.
Sitter Profile Image: Skylar S.
Verified Enhanced Background Check
Skylar S.
$63
total per night
5.0 out of 5 stars
53 reviews
9 repeat clients
10 years of experience
Canyon Lake, CA, 92587

We are so grateful to have found Skylar! From the moment she walked in, Kourtney and Khloe warmed right up to her and felt completely comfortable. Skylar is so easy to communicate with and keeps us updated, which really puts our minds at ease. She’s reliable, kind, and you can tell she truly loves animals. Knowing our girls are cared for and loved while we’re away means everything. We are super looking forward to having her help us with our pups again.

Profile image
Michelle S.
Sitter Profile Image: Paige G.
Verified Enhanced Background Check
Paige G.
$63
total per night
4.8 out of 5 stars
11 reviews
3 repeat clients
3 years of experience
Menifee, CA, 92586

Paige communicates very well, was punctual and took good care of our dogs. We wouldn’t hesitate to use her again or refer her.

Profile image
Jason & Stacey O.
Sitter Profile Image: Keiona D.
Verified Enhanced Background Check
Keiona D.
$84
total per night
5.0 out of 5 stars
7 reviews
3 repeat clients
13 years of experience
Winchester, CA, 92596

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.

Sitter Profile Image: Kerrie M.
Verified Background Check
Kerrie M.
$70
total per night
5.0 out of 5 stars
79 reviews
30 repeat clients
10 years of experience
Sun City, CA, 92586

I am so thankful I picked Kerrie to watch my 3 furbabies. No one has ever watched them except family so I was very nervous. Kerrie was wonderful with them, very patient with my timid girl. She sent me updates and pictures daily. She cleaned up the house and vacuumed all the doggie hair up before I got home. After a week my home looked perfect just the way I left it. My pups are so relaxed and happy I know she took good care of them. As long as she’s available we have found a perfect dog sitter. Thank you Kerrie for loving my pups. ❤️

Profile image
Karen B.
Sitter Profile Image: Kaylee Dawn M.
Verified Enhanced Background Check
Kaylee Dawn M.
$98
total per night
5.0 out of 5 stars
6 reviews
17 years of experience
Menifee, CA, 92584

Kaylee was great and Breda loved her and so did we.

Profile image
mary d.
Sitter Profile Image: Mariajose I.
Verified Enhanced Background Check
Mariajose I.
$56
total per night
8 years of experience
Menifee, CA, 92584

About: My love for animals runs deep—I’ve raised three cats from the time they were tiny kittens, and I’m currently training and caring for my energetic puppy, Otis. One of my cats, Lua, is named after the moon in Portuguese, a nod to my love for peaceful, nurturing energy—which I bring into every pet-sitting experience. Pet care fits perfectly into my daily life because I’m home most of the time with my own pets—my puppy Otis and my cat Lua. Caring for them is already part of my everyday routine, from feeding and walks to playtime and cuddles. Since I’m home-based, I have the flexibility and time to give other pets the same level of attention and love. Whether it’s drop-ins or extended stays, I can easily fit pet care into my schedule and treat every animal like family In my home, I create a calm, safe, and pet-friendly environment where animals feel comfortable and cared for. I stick to their usual routines as much as possible—feeding times, walks, play, and rest—so they feel secure and at ease. I also provide lots of love, attention, and gentle supervision to make sure they’re happy and healthy.

Sitter Profile Image: Carisma P.
Verified Enhanced Background Check
Carisma P.
$46
total per night
10 years of experience
Hemet, CA, 92545

About: I've been taking care of people's pets for ten years now and I still enjoy it! I've taken care of 10 dogs, 3 cats, and 2 bunnies for a total of 15 all at one time before. I have also previously taken care of chickens, fish, and lizards! I have watched puppies and I actually have my own senior dog that I care for at home. I am ready to care for your pet family! I am looking for work at the moment, so I have full availability right now! I will update with any changes, but I don't think it should impact my rover schedule. I am a very trustworthy person and I am very respectful of others and their property. If I needed someone to care for my pets I'd choose me, too!

Sitter Profile Image: Jessica V.
Verified Enhanced Background Check
Jessica V.
$38
total per night
5 years of experience
Hemet, CA, 92545

About: I’ve taken care of dogs since i could walk so i know how much patience and love they need and i will most definitely provide those things for ur pets. im also experienced with dog walking and bathing. i am currently unemployed so i will have all the time for ur pups or kitties :). they will be taken care of all day and night 24/7. I have a fenced yard (front and back) and one very friendly pup that will keep your pups company and i can crate them if needed.

Sitter Profile Image: Danielle H.
Verified Enhanced Background Check
Danielle H.
$67
total per night
10 years of experience
Homeland, CA, 92548

About: I put a lot of time and focus into caring for my fur babies for majority of my life. I’ve put time into caring for many others as well who trusts me to foster their pups over time while they are away on vacation or deployed. Let me care for yours too. Currently able to do early morning and mid day / evening walks when the weather cools down a little. Night time walks are possible but I will be accompanied by someone most nights. I have two fur babies of my own. One is kennel trained and the other is like a service dog. We free feed our pets and they go on at least a half mile to a mile walk every day to every other day when the weather is cool enough. I take the pets out or let them out every two to four hours so they can go potty. Water is ALWAYS accessible!

Sitter Profile Image: Kaylee S.
Verified Enhanced Background Check
Kaylee S.
$35
total per night
5.0 out of 5 stars
4 reviews
1 repeat client
5 years of experience
Hemet, CA, 92543

Very professional!

Profile image
Dr. Anne S.
Sitter Profile Image: Rachel L.
Verified Enhanced Background Check
Rachel L.
$88
total per night
5.0 out of 5 stars
3 reviews
7 years of experience
Menifee, CA, 92584

About: I have tons of experience working with all kinds of pets, from dogs and cats to bunny’s and chinchilla’s. I have previous experience working at a pet resort where I looked after dogs, cats, as well as horses while owners were away. I also have experience working in a doggy daycare with both small dogs and large dogs. In addition to this I also have experience working at a pop-up veterinary clinics where we helped dogs and cats. I have worked with dogs and cats of all ages and sizes and feel comfortable working with dogs that may be dog reactive. If needed I am also able to give your pet medication orally. My availability it’s pretty open, I am able to help take care of your pet(s) Wednesday through Sunday at whatever time that you will need! I am able to take your pets outside to use the bathroom and play, and can also crate your dog(s) when I'm not there if that's what you're most comfortable with. I will also make sure your pets have food and water available.

1 / 1
View more sitters

Over 201
pet parents in Winchester have booked house sitting

Winchester pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Sierra is amazing!! I was able to book her last-minute as my family was going out of state for the weekend (0/10 recommend BTW. Please don’t do it if you can help it). We have 2 young dogs - a cane corso and a frenchie, and believe it or not, the CC is the people lover out of the two! My Frenchie is usually the one who’s only comfortable around us, and even then, she’ll only be nice to some of us. Sierra had both dogs cuddling and loving on her from Day 1! She made sure both were fed, watered, and loved on from morning until night/bedtime and sent multiple pictures of them throughout each day. She kept in constant contact with me as well. Highly recommend!!

Profile image
Tehani A.
House Sitting
5.0 out of 5 stars

Makaila was amazing and my girls loved her! She sent updates throughout the day and treated my puppies as her own.

Profile image
Karrisa S.
House Sitting
5.0 out of 5 stars

I cannot explain the peace of mind having her at my house with my panicky dog during fireworks gave me. My dogs absolutely loved her. I could not be happier, she deserves every single one of these 5 stars.

Profile image
Mary C.
House Sitting
5.0 out of 5 stars

There aren't enough good words in the world to describe Diane! We have a difficult dog that also needed medication and special attention. She not only stayed here and kept her company, but she did the following without even being asked: •Trained our dog •Walked her multiple times per day •Played with her constantly •Sent constant photos, videos, texts and updates •Kept a written schedule of her medication •Put a shelf and all of the contents back after our dog knocked it down •She even cleaned the house before we got home! She is honestly worth twice the rate she charges. I will never use another pet sitter in the area. She made our vacation so much more enjoyable because we knew our dog was in amazing hands.

Profile image
Tera K.
House Sitting
1 / 1
Find pet care near you

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 $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 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 Feb 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.

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 Feb 2026, there are 1,172 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, 85% 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.