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: Nikolaas P.
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Nikolaas P.
from
$20
per night
5.0 out of 5 stars
18 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: Robbyn W.
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Robbyn W.
Star Sitter
from
$40
per night
5.0 out of 5 stars
3 reviews
3 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: 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: 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: Jessica B.
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Jessica B.
from
$30
per night
5.0 out of 5 stars
6 reviews
1 repeat client
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: Wanda B.
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Wanda B.
from
$31
per night
30 years of experience
Suffolk, VA, 23434

About: I have cared for a wide range of animals to include lizards, turtles, ferrets, dogs and cats for over 30 years. Senior babies are welcome as well as special needs. I work from home and have flexibility to provide the attention and care a pet may need throughout the day and evening (frequent potty breaks and feedings). I can provide the care that any pet parent requests with reasonable accommodations. Whether it is a special walk or dietary instruction, I can easily provide the care.

Sitter Profile Image: Robert B.
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Robert B.
from
$68
per night
5.0 out of 5 stars
13 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: Chainey L.
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Chainey L.
Star Sitter
from
$28
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
5 years of experience
Wakefield, VA, 23888

About: I’ve owed 4 Labrador retrievers, and still currently have two, one is my duck dog and one’s my old retired boy. I love animals. We enjoy daily walks, and mental stimulation! They get plenty of outdoor time as well as one on one time! I’m currently working as an estimator from home so I have plenty of free time for animals and making sure they get the proper care they need while under my supervision! I have all necessities for animals. I have an out door dog run, I have indoor kennels, I have a designated area inside, I give mental stimulation toys and treats. I make sure the dogs are going outside atleast every two hours insuring the have there energy out and not missing any potty breaks man

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 was great! She came over to walk our dog a couple times to build trust with her, and she sent us lots of pictures and updates! We knew our puppies were in good hands with her!

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Hanna C.
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: DeHaven S.
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DeHaven S.
from
$50
per night
5.0 out of 5 stars
30 reviews
6 repeat clients
10 years of experience
Carrollton, VA, 23314

Dehaven and Ashlee took great care of our dog and our home while we were gone! They were very understanding of our dogs needs and did a great job while we were gone. They were great communicators and kept us up to date on how things were going which was very helpful. We cannot thank them enough!

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Philip N.
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: Armonee H.
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Armonee H.
from
$15
per night
5.0 out of 5 stars
5 reviews
3 repeat clients
11 years of experience
Suffolk, VA, 23434

I would ABSOLUTELY book Armonee again! I was very apprehensive about leaving my dog with someone for the first time, but Armonee kept me updated throughout the entire week and sent photos/videos. Mila was well cared for, and that made it easier for me to enjoy my trip.

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Chandora W.
Sitter Profile Image: Erin J.
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Erin J.
from
$30
per night
5.0 out of 5 stars
11 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: Felicia H.
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Felicia H.
Star Sitter
from
$26
per night
5.0 out of 5 stars
17 reviews
4 repeat clients
5 years of experience
South Norfolk, Chesapeake, VA, 23324

Felicia was amazing! We came home to happy dogs and a clean home. Thank you for everything. We’ll be in touch for another upcoming trip we’ll need your services for!

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Tiffany L.
Sitter Profile Image: Kimberly H.
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Kimberly H.
from
$75
per night
5.0 out of 5 stars
17 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
14 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: Anna Mei D.
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Anna Mei D.
Star Sitter
from
$30
per night
4.9 out of 5 stars
110 reviews
42 repeat clients
13 years of experience
Greater Wythe, Hampton, VA, 23661

Anna is terrific! We have not used Rover before and were a little hesitant with someone staying in our home when we plan on going on vacation. Several weeks before our trip, Anna Mei came to our house and spent about 2 hours with us and our dogs. That was a great way for us to get to know each other and see how comfortable our dogs were with her and she with our dogs. At her suggestion, we spent one night in a hotel as a trial run while she stayed with our dogs. Everything went really well, and she kept us updated on what was going on. She definitely earned our trust, and we are relieved that we found a reliable sitter for when we are on our vacation. We will definitely request her again. Thanks Anna!

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David B.
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: Kari H.
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Kari H.
from
$60
per night
5.0 out of 5 stars
19 reviews
3 repeat clients
15 years of experience
Deep Creek South, Chesapeake, VA, 23323

Kari was AMAZING!!!! She let me know when she got to my house and sent me soooo many pictures of my fur babies as if I was there which I appreciate more than anything! One of my dogs was scratching a lot so she let me know and gave her some benadryl to help. Kari is seriously the best and I will definitely be using her again!

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Paige W.
1 / 1
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Over 4
pet parents in Windsor have booked house sitting

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 Windsor is $40

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 $40 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 359 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, 88% of Windsor house sitters respond in under an hour.

House sitters in Windsor have an average of 17 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.