House Sitting in Windsor

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

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Top rated Windsor 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: Kelly H.
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Kelly H.
Star Sitter
from
$45
per night
5.0 out of 5 stars
49 reviews
15 repeat clients
30 years of experience
Suffolk, VA, 23434

Kelly is hands down the best pet sitter in the area. She goes above and beyond for the pets, & her pics are the best! I can tell my boys (a Corgi who's very vocal, and a Hound Dog) love her very much and they don't even pout when we return from a trip anymore!

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JoAnna M.
Sitter Profile Image: Robbyn W.
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Robbyn W.
Star Sitter
from
$40
per night
5.0 out of 5 stars
3 reviews
4 repeat clients
3 years of experience
Suffolk, VA, 23434

I can’t say enough good things about Robbyn. Jackson immediately connected with her, and he was more relaxed than I’ve ever seen him for a high energy puppy. She kept the place spotless, communicated regularly, and sent plenty of photos so I always knew he was doing well. I’m truly grateful for the care she provided, and I will definitely be booking with her again.

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Shani T.
Sitter Profile Image: Nikolaas P.
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Nikolaas P.
from
$20
per night
5.0 out of 5 stars
21 reviews
6 repeat clients
15 years of experience
Franklin, VA, 23851

Nikolaas was an amazing dog sitter to our two pups. Our boys can get anxious without us, but they loved him. He was super communicative, sent lots of updates and pictures, and I felt much more at ease leaving home. We will definitely book him in the future.

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Ellen D.
Sitter Profile Image: Armonee H.
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Armonee H.
from
$20
per night
5.0 out of 5 stars
11 reviews
4 repeat clients
11 years of experience
Suffolk, VA, 23434

Armonee was great! She communicated a lot with us, keeping us updated with how all of the animals were doing, which was very comforting as this was our first time having her sit for us. She followed the animals' schedules and coordinated very well between other clients and us. We are already booked with her again!

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Breanna V.
Sitter Profile Image: Jessica B.
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Jessica B.
Star Sitter
from
$32
per night
5.0 out of 5 stars
10 reviews
2 repeat clients
20 years of experience
Suffolk, VA, 23434

Jessica did a great job caring for our pets. She provided an update with pictures daily and was always available to chat. Thank you for taking such great care of our girls!

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Alexis B.
Sitter Profile Image: Chainey L.
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Chainey L.
Star Sitter
from
$28
per night
5.0 out of 5 stars
7 reviews
3 repeat clients
5 years of experience
Wakefield, VA, 23888

So pleased! Chainey communicates frequently, is responsive, is great with our dogs and home looked in better shape when we got home than when we left 😆

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Leigh A.
Sitter Profile Image: Ashley R.
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Ashley R.
from
$26
per night
20 years of experience
Suffolk, VA, 23435

About: Hi! My name is Ashley, and I have been around animals my entire life. I have experience caring for small, medium, and large dogs with a variety of personalities and energy levels. Whether your pet loves long walks, playtime, or simply having company, I am happy to provide the care and attention they need while you’re away. I am also comfortable around cats and understand that every pet has their own routine and preferences. I know how important it is to find someone you trust with your furry family members, and I will treat your pets with the same care, patience, and affection that I would give my own. I look forward to meeting you and your pets! My availability is Wednesday evening through Sunday evening each week. I am available for walks, drop-in visits, and pet sitting during that time and will do my best to accommodate your pet’s routine and needs. I don’t currently have a pet in my home, but I have spent my life around dogs and have experience caring for pets with different personalities, sizes, and energy levels. I understand how important routines are for animals, and I strive to provide a safe, loving, and comfortable environment while they are in my care.

Sitter Profile Image: Alexa N.
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Alexa N.
from
$20
per night
5.0 out of 5 stars
2 reviews
5 years of experience
Suffolk, VA, 23435

Alexa was wonderful with Rocky and Laika. She was available with short notice and treated them so well. She communicated incredibly well and was very respectful of our space. I would have her come back and help out with the dogs any time.

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Erin W.
Sitter Profile Image: Chloe B.
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Chloe B.
from
$45
per night
5.0 out of 5 stars
5 reviews
1 repeat client
14 years of experience
Suffolk, VA, 23434

About: I have a 14 yr old Chihuahua and occasionally a 3 yr old rotwieler. I am familiar with diets and special care that any dog or pet may need. I spend a lot of time outside on hikes or just taking walks. I will provide you fur baby with plenty of games and stimulation. I consider my dog my whole world and I know how important it is that they are left in a safe and caring environment while you are away. There is plenty of space

Sitter Profile Image: Sijie Y.
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Sijie Y.
from
$50
per night
10 years of experience
Suffolk, VA, 23434

About: I have ten years of experience caring for dogs and cats including walking feeding bathing senior care medication routines and calm reliable companionship daily needs😊 I work mornings from eight to twelve and am available afternoons evenings and weekends for walks drop ins boarding playtime feeding and attentive care daily.🥰 I follow owner instructions closely maintain clean spaces monitor behavior carefully provide updates secure leashes doors and routines and prioritize safety comfort and stress free care always.🩷

Sitter Profile Image: Robert B.
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Robert B.
Star Sitter
from
$68
per night
5.0 out of 5 stars
14 reviews
3 repeat clients
15 years of experience
Suffolk, VA, 23434

Robert spent a weekend caring for our fur babies. We had a meet and greet prior to his stay and he did a thorough assessment of our animals needs to make sure he provided top notch care. Over the weekend he sent pictures and updates. I knew my fur babies were well-taken care of.

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Anastasiia T.
Sitter Profile Image: DeHaven S.
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DeHaven S.
from
$50
per night
5.0 out of 5 stars
30 reviews
7 repeat clients
10 years of experience
Carrollton, VA, 23314

DeHaven took the BEST care of our two pups and provided frequent updates. We truly appreciate not having to worry about our furr kids while we are away. Highly recommend for any future sits!!!

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Devon C.
Sitter Profile Image: Erin J.
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Erin J.
from
$30
per night
5.0 out of 5 stars
13 reviews
1 repeat client
30 years of experience
Portsmouth, VA, 23704

Erin was amazing! She was very easy to communicate with to set up the booking, asked plenty of questions to make sure Diablo and I were taken care of, and sent me picture and video updates of them enjoying each other's company. If possible, I will book her again in the future!

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Spencer W.
Sitter Profile Image: Angie S.
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Angie S.
from
$85
per night
5.0 out of 5 stars
21 reviews
11 repeat clients
40 years of experience
Suffolk, VA, 23434

Angie bailed us out with last minute booking. She was responsive and caring. Bella and Rocco were well cared for while we were away. We will book with her again.

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Gina N.
Sitter Profile Image: Anna Mei D.
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Anna Mei D.
from
$35
per night
4.9 out of 5 stars
113 reviews
42 repeat clients
16 years of experience
Greater Wythe, Hampton, VA, 23661

Anna was awesome!! She was professional and she definitely knows how to interact with animals. She was great with our dogs Yoda and Marvin and she sent us photos and videos which kept us at ease as well. She is very trustworthy and we will definitely be using her for future housesitting visits!!

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Michael N.
Sitter Profile Image: Felicia H.
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Felicia H.
Star Sitter
from
$26
per night
5.0 out of 5 stars
21 reviews
4 repeat clients
5 years of experience
South Norfolk, Chesapeake, VA, 23324

I have booked with Felicia three times now, and she has consistently provided a great experience. What stands out most is her attention to detail; she asks a lot of questions upfront to make sure she fully understands my dog's routine and comfort levels. It’s clear she wants to get everything exactly right, which gives me a lot of peace of mind while I'm away. She is reliable, communicative, and truly cares about the well being of the animals in her care. I highly recommend her if you’re looking for someone thorough and attentive!

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Mari R.
Sitter Profile Image: Kimberly H.
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Kimberly H.
from
$75
per night
5.0 out of 5 stars
19 reviews
4 repeat clients
20 years of experience
Portsmouth, VA, 23703

Kim has been amazing throughout my time away from my dogs. Kept them on their schedule, made adjustments when my travel plans unfortunately got changed. I will definitely be rebooking with her in the future.

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Rebecca S.
Sitter Profile Image: Emmanuel S.
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Emmanuel S.
Star Sitter
from
$40
per night
5.0 out of 5 stars
15 reviews
5 repeat clients
10 years of experience
Norfolk, VA, 23508

Emmanuel was an amazing pet sitter! He watched my 5 fur babies while I was gone for a week and they got along with him so well! He was very attentive to my fur babies and he enjoyed time spent with them! He treated them like they were his own. He was very communicative, providing me daily updates with adorable pictures and videos! He even got my antisocial cat to warm up to him and interact with him, which was a 1st! He also did a great job keeping the place clean while caring for the fur babies. I feel like my pets definitely lucked out with having an amazing sitter and new friend! I would highly recommend booking Emmanuel as your next pet sitter!

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Frantaisia R.
Sitter Profile Image: Zaine M.
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Zaine M.
from
$45
per night
5.0 out of 5 stars
2 reviews
2 years of experience
Courtland, VA, 23837

Very reliable and great with our dogs!

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Sarah P.
Sitter Profile Image: Daniela U.
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Daniela U.
from
$100
per night
5.0 out of 5 stars
8 reviews
1 repeat client
9 years of experience
Suffolk, VA, 23437

About: I have many years of experience caring for both dogs and cats. I have a senior dog that I adopted in 2015 and in 2020 I helped raise a puppy from 8 weeks old. They were both raised with kittens as well. Through these experiences, I have learned how to care for different animals of different age groups. I currently work 9 am-5pm Monday through Thursday so I am available after 5pm those days. On Fridays, I am available from 8 am-1pm. I am available all day Saturdays and Sundays. I have a spacious apartment that is pet friendly and equipped with two dog parks and a lake with plenty of walking area. My pets are friendly and love play dates with new friends!

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  2. 2. Meet & Greet

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  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 Windsor is $42

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 Windsor 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 Windsor on Rover as of Jun 2026 was about $42 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 Windsor 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 1,250 house sitters in Windsor. 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 Windsor house sitters respond in under an hour.

House sitters in Windsor have an average of 15 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 Windsor.

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. Windsor 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.