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: Jessica M.
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Jessica M.
from
$40
per night
5.0 out of 5 stars
4 reviews
1 repeat client
10 years of experience
Winchester, VA, 22601

Was gone for about 3 days. Jessica was able to provide me with a morning and afternoon report on how my pets were doing and sent me plenty of pictures. I was so grateful and was able to enjoy my trip knowing that they were in good hands. My 2 cats and pup were so comfortable with her. Definitely recommend and will rebook again!

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Jessica N.
Sitter Profile Image: charlotte g.
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charlotte g.
Star Sitter
from
$40
per night
5.0 out of 5 stars
3 reviews
2 repeat clients
8 years of experience
Winchester, VA, 22601

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.

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Giovanna C.
Sitter Profile Image: Natalie B.
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Natalie B.
from
$55
per night
5 years of experience
Winchester, VA, 22601

About: I work full time at Shenandoah University and am joining Rover to formalize my side hustle, which Ive largely managed through word of mouth thus far. I’ve lived with dogs for about 25 of my 30 years of life - mostly hounds (most recently 2 bassets). And I’ve watched dogs of all sizes, the smallest being a chihuahua mix and the largest a Great Dane. Over the last 5 years or so, I’ve dog sat for friends, family, and connections in the Winchester area. The longest engagement was 6 weeks, but I normally do long weekends or week long jobs. All animals are different and I respect you, their owner, to tell me what’s best for your furry friend. I also will be transparent and over communicate with you so we both can be confident your animals have everything they need. I’m comfortable dispensing medication - including to the really picky ones (I can take a pill/pill pocket and sculpt it pretty much exactly the same shape and size as any mainstream kibble brand). I have experience with puppies and with our senior citizens, who both just need a little extra care and attention. I feel comfortable listening to animals and getting to know their personalities, which are all so different yet equally endearing. If they are trying to say something, though, I feel pretty confident I will notice it - especially after we’ve spent a few hours together. And, if they’re trying to say something and I don’t understand? I’ll reach out just to make sure. I just really, really love animals. I most often watch dogs but have also cared for cats, lizards, bunnies, chickens, and horses (although horses were largely just feeding and brushing/attention). I also have a rescue cat of my own, Luna, who has made me certain I’m equally a dog person AND a cat person. I work 9-5 M-F, and occasionally am tied up on weekends with happenings on campus. I can take an hour lunch (and flex a bit beyond if necessary) to visit the animals for attention and potty breaks. I am single, sober, and genuinely grateful for the work and the company. Animals have so much love to give, and i try to reciprocate that love indiscriminately. Thanks for your consideration and please let me know if I can answer any questions, hop on a zoom call, or speak to any specific needs you find important. No request is too small and I’m grateful for any and all details I can use to keep your animals feeling secure, loved, and cared for in your absence. I work full time at Shenandoah University as an Administrative Assistant in the Office of Global Engagement. My role is in-person on the main campus in Winchester. My routine hours are 9-5 with an hour lunch around 12 or 1. But, there’s a lot of flexibility, especially over the summer when the students are back home. My team is small and I am able to shift my hours when I communicate with them in advance (I.e. I’ll take 2 hours midday but clock in at 8, etc). Outside of work, my schedule largely centers around community and service work. I’m really involved with the recovery community and attend several meetings and events a week, although I can be flexible there too. Most days I’m up no later than 7 am and asleep by 11. But all these things can flex, depending on your and your pets needs. I live alone with a stray-turned-adopted cat named Luna (who I’m preparing to spay, which is part of my need for a more stable second income!). My place has a small fenced area in the back, enough room for a pup to potty but not much more. But I’m also about a half a mile from Jim Barnett Park and I love their walking trails and their dog park. I’d prefer to house sit at your house, but I’m open to certain scenarios if I can ensure your animal is comfortable in my space. Let’s talk about the details!

Sitter Profile Image: Christopher P.
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Christopher P.
from
$55
per night
5.0 out of 5 stars
12 reviews
2 repeat clients
13 years of experience
Winchester, VA, 22601

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!

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Tamara K.
Sitter Profile Image: Michelle S.
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Michelle S.
from
$35
per night
5.0 out of 5 stars
29 reviews
10 repeat clients
43 years of experience
Winchester, VA, 22601

Michelle was so good about keeping me updated about our pets and how everything was going. Very quick to answer my calls and texts. I think the pets really enjoyed her because they followed Michelle to the door when she was leaving. My mind was at complete ease and I would rebook with Michelle.

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Jean T.
Sitter Profile Image: Shannon B.
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Shannon B.
from
$55
per night
5.0 out of 5 stars
4 reviews
5 years of experience
Winchester, VA, 22602

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!

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Denise F.
Sitter Profile Image: Kathy G.
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Kathy G.
from
$75
per night
5.0 out of 5 stars
58 reviews
18 repeat clients
30 years of experience
Winchester, VA, 22601

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.

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Jessica F.
Sitter Profile Image: Judy M.
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Judy M.
from
$35
per night
7 years of experience
Winchester, VA, 22601

About: Caring for animals has been a major part of my life since I was 15, beginning with pet sitting for neighbors and growing into years of hands-on experience with dogs of all breeds, sizes, ages, and temperaments. My family fostered through PetConnect Rescue for five years, where I helped care for and train rescue dogs ranging from small Shiba Chihuahua mixes to larger Boxer Pitbull mixes. I also worked with Animal Au Pair in Loudoun County, gaining experience with large breeds including Great Pyrenees and Saint Bernards. Additionally, I’ve personally rehabilitated an anxious rescue Shiba Inu mix who was initially fearful of people and the outdoors, helping her become more confident, comfortable, and social over time. I’m dedicated to providing patient, reliable, and compassionate care tailored to each pet’s unique needs. Pet sitting will be my full-time focus during summer break between college semesters, allowing me to maintain a very flexible schedule and dedicate quality time to your pets. I’m available to travel to surrounding areas and provide reliable, attentive in-home care to keep your pups comfortable in their familiar environment. I offer flexible visit scheduling throughout the day to ensure your pet receives frequent attention, regular potty breaks, scheduled feedings, and personalized care based on their needs. Crating can also be provided between visits if requested. Longer visits can be arranged for pets who may need additional companionship, exercise, or supervision. I’m happy to provide regular updates and photos throughout the day so you can feel confident and connected while you’re away.

Sitter Profile Image: Suellen W.
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Suellen W.
from
$30
per night
2 years of experience
Winchester, VA, 22601

About: I’ve had dogs my entire life, and got into dog training 2 years ago. I assisted a dog training company with the dogs they would board and care for, and assisted with multiple training outings. I also raised and trained my own service animal. I’m currently working part time, and will focus solely on providing care for your pet and home. They are my number one priority and love to do things with them. I will take them on long walks and do training with them to get their brain going. I’ll make sure their meals are extra tasty and made with love.

Sitter Profile Image: Victoria L.
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Victoria L.
from
$35
per night
4.8 out of 5 stars
6 reviews
23 years of experience
Winchester, VA, 22602

Victoria provided frequent comms and was very responsive. Great job, we will definitely use her again!

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Stu Y.
Sitter Profile Image: Kathryn W.
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Kathryn W.
from
$50
per night
5.0 out of 5 stars
1 review
10 years of experience
Winchester, VA, 22601

Katherine was absolutely great with Donner and Murphy during the storms we had yesterday. Played with them cuddled with them to comfort them. We’ll definitely have back as needed.

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Pamela T.
Sitter Profile Image: Linda K.
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Linda K.
from
$60
per night
5.0 out of 5 stars
114 reviews
45 repeat clients
18 years of experience
Winchester, VA, 22602

About: (Formerly Kamp Kelley) I have been fostering small dogs for a rescue group in No. VA. for the last 9 years (my aching back doesn’t allow me to work with dogs larger than 20 lbs)--prior to that I fostered cats and kittens. I has experience with many types of small dogs—especially Shih Tzu’s and Llasa Apso’s, but also Yorkshire Terriers, Basset Hounds, Pom's, Toy Poodles, etc. My expertise is in rescuing and caring for senior and special need dogs. Since I have a dog-friendly house and a large-fenced yard (1/4 acre) for them to run and play in, I decided to become a dog-sitter 5 years ago. I believe in loving and treating your fur-baby like my own! We keep her home and yard dog proof so your little angel will be in a safe, relaxed, dog-friendly, and loving environment! Because I am retired, my schedule is very flexible. I'm retired and except for occasional trips to the store, bi-weekly Bridge games. monthly book group and a occasional meeting, I'm home ALL THE TIME. At this point, I am accepting only ONE dog at a time EXCEPT if there are 2 dogs from the same household. Same for cats. I have a large, fenced yard that can be separated off. I have lots of dog equipment. For example large crates if your dog is used to being crated, bowls, beds and cushions, a big bed for them to share with me, jackets, leashes, kongs and lots of love and affection. Same for cats--EXCEPT, I let them out only on the back deck (enclosed).

Sitter Profile Image: Mary M.
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Mary M.
from
$50
per night
5.0 out of 5 stars
12 reviews
6 repeat clients
2 years of experience
Winchester, VA, 22601

Mary was so great with my three legged dog and my cat. She was communicating with me the entire time I was away, along with pictures and updates. I was able to enjoy my weekend because I wasn't worrying about my fur babies back home the entire time. Would recommend to a friend ✨️

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Briana W.
Sitter Profile Image: Haley Z.
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Haley Z.
from
$55
per night
5.0 out of 5 stars
137 reviews
45 repeat clients
17 years of experience
Stephens City, VA, 22655

Haley is great! I could tell our dogs were well loved and cared for when we returned home. She was always available to communicate with and sent daily updates. We will definitely request her to watch our dogs again in the future and highly recommend her to others.

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Dana F.
Sitter Profile Image: Julia Z.
Verified Enhanced Background Check
Julia Z.
from
$60
per night
4.9 out of 5 stars
20 reviews
6 repeat clients
5 years of experience
Winchester, VA, 22601

She was so patient with our big dog and even played ball with him. It was so comforting to know our dog was being cared for as if we were there.

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Emalou D.
Sitter Profile Image: Ruby K.
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Ruby K.
from
$40
per night
5.0 out of 5 stars
1 review
10 years of experience
Winchester, VA, 22602

Ruby was excellent. She was flexible and responsible. She followed instructions and kept us updated. Thank you Ruby!

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Angela E.
Sitter Profile Image: Alex M.
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Alex M.
from
$80
per night
5.0 out of 5 stars
3 reviews
1 repeat client
15 years of experience
Winchester, VA, 22601

About: I have owned and trained dogs most of my life, grew up on a farm with all types of pets and find it second nature to treat them like family. I currently work from home and have a very flexible schedule. I can house sit, drop in or stay with your pet as long as you need someone. My dog has a fenced in yard and is at day care for socialization M-F so I can have my full attention on your dog. I currently work from home part time so I have plenty of time for your pet! I am awake early and have a flexible schedule to fit yours. I make sure you and your pet are comfortable with me and follow instruction when caring for your pet. You know your pet best and I want them to be happy and content with me.

Sitter Profile Image: Jennifer L.
Verified Enhanced Background Check
Jennifer L.
Star Sitter
from
$50
per night
5.0 out of 5 stars
30 reviews
9 repeat clients
10 years of experience
Cross Junction, VA, 22625

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!

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Kim C.
Sitter Profile Image: Sierra C.
Verified Enhanced Background Check
Sierra C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
9 reviews
3 repeat clients
7 years of experience
Boyce, VA, 22620

Sierra took amazing care of my pups at my house while I was out of town for a few days!

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McKenna C.
Sitter Profile Image: Stefany P.
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Stefany P.
from
$60
per night
3.7 out of 5 stars
3 reviews
5 years of experience
Winchester, VA, 22602

About: Life is Good with pets! I have been providing professional pet care services for dogs for over 5 years. I have always had different dogs in my life from childhood to adulthood. I’ve seen how happy my own pet is from taking him on regular walks and I am excited to provide this same experience for other pets. I have a large, fenced yard in a semi-rural neighborhood, and I enjoy taking dogs on nice long walks. Pets are allowed on furniture to snuggle and I am also happy to crate train pets, if preferred. I am currently working from home, so I have most of my time to give attention and love to your pet. I am happy to provide these services at all times. I have plenty space and a fenced yard for your pet to play or simple go on potty breaks, if needed. The services requested will be depending on the customers offer :)

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Over 507
pet parents in Winchester have booked house sitting

Winchester pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Kristine is a warm and caring individual and my dogs picked up on that immediately. She was fantastic with our three German Shepherds. She took great care of our dogs and our home while we were away. She was respectful of our property, cleaned up after herself and the dogs, and went above and beyond by mopping up after a rainstorm and even throwing linens in the wash before we returned. It gave us so much peace of mind knowing everything was being handled so thoughtfully. Great communication, too. I would absolutely book Kristine again and highly recommend. Kristine, if you’re reading this, thank you so much for putting up with all the shedding, the Shepherds were dropping their coats like crazy.

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Alesha R.
House Sitting
5.0 out of 5 stars

Katherine was absolutely great with Donner and Murphy during the storms we had yesterday. Played with them cuddled with them to comfort them. We’ll definitely have back as needed.

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Pamela T.
House Sitting
5.0 out of 5 stars

Charlotte came for the day to get to know Finn, our little dog, before coming to stay over in a few weeks time. We left for the day and when we returned Finn was sitting next to her on the sofa looking content and happy:) Charlotte is a calm and friendly person who understands pups very well. :)

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Carly G.
House Sitting
5.0 out of 5 stars

Shannon was amazing. Our little guys loved being with her. Def will be using her again. Her communication about what the dogs were doing was great. Highly recommend

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Melissa S.
House Sitting
5.0 out of 5 stars

Ruby was excellent. She was flexible and responsible. She followed instructions and kept us updated. Thank you Ruby!

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Angela E.
House Sitting
5.0 out of 5 stars

Bailey loves when Riona visits! She takes such good care of her and sends pictures that shows she’s comfortable with her. Thank you!

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Cynthia M.
House Sitting
5.0 out of 5 stars

Julianna provided excellent services taking care of Shadow and Finn. She established a sound relationship with both dogs and they didn't seem to have missed us while we were on vacation. That was the objective and it was met in all regards. Great work!

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Walter K.
House Sitting
5.0 out of 5 stars

Katie had excellent communication throughout our trip and handled everything so well. Our dogs have a large size difference and she took care of them well. Highly recommend.

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Destiny B.
House Sitting
5.0 out of 5 stars

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!

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Donna C.
House Sitting
5.0 out of 5 stars

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!

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Betty C.
House Sitting
5.0 out of 5 stars

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!

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Beth S.
House Sitting
5.0 out of 5 stars

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!

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Tamara K.
House Sitting
5.0 out of 5 stars

Alexsys is amazing. Oscar loves her and I feel like he's well taken care of when I have to leave him at home.

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Bob C.
House Sitting
5.0 out of 5 stars

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!

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Cindy W.
House Sitting
5.0 out of 5 stars

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!

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Amy S.
House Sitting
5.0 out of 5 stars

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!

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Heather W.
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 $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 Jun 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 Jun 2026, there are 303 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.