Dog Boarding in Windsor, VA

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Top rated Windsor dog boarders

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: Rachel C.
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Rachel C.
Star Sitter
from
$30
per night
4.9 out of 5 stars
97 reviews
38 repeat clients
7 years of experience
windsor, VA, 23487

Rachel was great with communication for pre drop off, drop off, during stay and pickup. I was able to bring my pup over for a meet and greet with her and her dogs prior to the boarding. Has a great sized yard and friendly dogs. She sent video updates everyday which I loved. I would recommend and will be using her again in the future!

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momo j.
Sitter Profile Image: Megan M.
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Megan M.
from
$35
per night
5.0 out of 5 stars
13 reviews
1 repeat client
15 years of experience
Suffolk, VA, 23434

Megan was amazing I recently boarded my rescue Prince for the first time, and I couldn’t have asked for a better experience! Megan took such amazing care of Prince during his two-night stay. She went above and beyond—sending me some of the best photos and videos I’ve ever had of him, including clips of him playing and socializing with larger dogs (which was a first for him!). It meant so much to see him having that kind of fun and confidence. Megan also kept me updated with daily “doggy report cards” and personalized notes, which were such a thoughtful touch. When I picked him up, it was clear he had an incredible time—he was almost sad to leave! He even made a new best friend with her dog, Kava. I’m so grateful for the care and attention Megan gave, and I will absolutely be booking with her again. Truly a 5-star experience from start to finish!

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Nicole B.
Sitter Profile Image: Milena B.
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Milena B.
Star Sitter
from
$40
per night
5.0 out of 5 stars
25 reviews
7 repeat clients
8 years of experience
Carrollton, VA, 23314

She was great with Milo. Milo doesn't usually get along with oher dogs, but got along great with her dog. I felt totally comfortable leaving Milo with her.

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Christy B.
Sitter Profile Image: Shelly S.
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Shelly S.
Star Sitter
from
$40
per night
5.0 out of 5 stars
183 reviews
56 repeat clients
30 years of experience
Suffolk, VA, 23437

My dogs LOVE going to Shelly's. She pays a lot of attention to them and they come home exhausted. Shelly is very accommodating and always reachable. Great experience.

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Laura R.
Sitter Profile Image: Melody & Matthew D.
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Melody & Matthew D.
Star Sitter
from
$35
per night
5.0 out of 5 stars
82 reviews
41 repeat clients
10 years of experience
Suffolk, VA, 23434

For being a first time user and having my dog watched for the first time, I'm absolutely overly satisfied with the services we received! Communication was there, the process of meeting and greeting was smooth and easy, pictures were sent to me throughout my vacation(I LOVED), and just having the overall feeling that my dog was okay safe and well taken care of was a big PLUS for me being on vacation on the other side of the world! I could sit here and write a whole paragraph or more on all of the positive and my experience but, I will keep it short and say I just HIGHLY RECOMMEND! Thank you again for your services!

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Vincent F.
Sitter Profile Image: Robert B.
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Robert B.
from
$40
per night
5.0 out of 5 stars
13 reviews
3 repeat clients
15 years of experience
Suffolk, VA, 23434

Robert and Taylor took amazing care of my young pitbull. They are very kind and friendly and really care about the well being of my baby. I will definitely be booking with them in the future.

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Limaris V.
Sitter Profile Image: Kimberly K.
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Kimberly K.
Star Sitter
from
$42
per night
5.0 out of 5 stars
23 reviews
8 repeat clients
35 years of experience
Western Branch South, CHESAPEAKE, VA, 23321

Kimberly and her boys were amazing. We don’t vacation often because we don’t like leaving our beloved Ollie, Kimberly has changed that. She was very informative and flexible. She kept us updated and made sure Oliver was comfortable. Can’t wait to book again

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Lasonya L.
Sitter Profile Image: Jessica K.
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Jessica K.
Star Sitter
from
$35
per night
5.0 out of 5 stars
103 reviews
32 repeat clients
20 years of experience
Smithfield, VA, 23430

Jessica and her family Treat our 3 boys like their own when they are there. Great communication and pictures of the boys are always a great touch too! Highly Recommend!

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Randal R.
Sitter Profile Image: Lisa R.
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Lisa R.
Star Sitter
from
$50
per night
5.0 out of 5 stars
341 reviews
120 repeat clients
10 years of experience
Suffolk, VA, 23432

Lisa took wonderful care of our dog! She was attentive and kind, and she sent me frequent updates on how he was doing. I highly recommend Lisa!

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Mollie B.
Sitter Profile Image: Jackie & Kevin K.
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Jackie & Kevin K.
Star Sitter
from
$35
per night
4.8 out of 5 stars
79 reviews
28 repeat clients
20 years of experience
Saunders, Newport News, VA, 23601

Well this was our Kobe first experience with Jackie or anybody since Covid came into our lives. Jackie made the process smooth and informative for us to know how our dog was doing we really appreciate that too so we thank you. She return our to us with good attitude and clean as he came there. So if anybody looking for an outstanding dog sitting Jackie is your best choice. We thank you again and will be using your service in the near future.

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James G.
Sitter Profile Image: Vania H.
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Vania H.
Star Sitter
from
$38
per night
5.0 out of 5 stars
59 reviews
24 repeat clients
20 years of experience
Suffolk, VA, 23434

The best she did everything to accommodate my Trudy. She also went out her way to be available at the time I arrived from airport even though my flight was delayed. People don't understand how hard it can be planning a vacation or getting away when you have a pet, Vania was a lifesaver and Trudy enjoyed her stay as well.

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Gabrielle M.
Sitter Profile Image: Julie & Kenneth N.
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Julie & Kenneth N.
from
$35
per night
5.0 out of 5 stars
150 reviews
58 repeat clients
10 years of experience
Norfolk, VA, 23505

I knew when I met Julie that this home was the right choice for our pup. There is nothing better than knowing your furry family member is in a good and loving environment while you're out of town. We could not have been happier and will use her and Kenneth again!

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Julie H.
Sitter Profile Image: Maria & Matthew R.
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Maria & Matthew R.
Star Sitter
from
$38
per night
5.0 out of 5 stars
51 reviews
10 repeat clients
30 years of experience
Great Bridge, Chesapeake, VA, 23322

This was our second time with María and Matthew, and once again they were fantastic! I feel so at ease knowing my fur baby is in such loving and reliable hands. Highly recommend!

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Sandra J.
Sitter Profile Image: Lauryn B.
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Lauryn B.
Star Sitter
from
$30
per night
5.0 out of 5 stars
45 reviews
15 repeat clients
12 years of experience
Newport News, VA, 23608

Lauryn was an incredible sitter! She accommodated all of my dogs’ needs and likes. She took care of my boys, Ace and Adonis, as if they were her own. I loved that she sent pictures and videos of them every day. It was such a bonus and put my mind at ease to see them having fun while I was away. I highly recommend her and we will be back! 🐾😊 Thank you Lauryn!

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Arianna G.
Sitter Profile Image: Gail T.
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Gail T.
Star Sitter
from
$35
per night
5.0 out of 5 stars
60 reviews
34 repeat clients
50 years of experience
Portsmouth, VA, 23707

Gail was wonderful with Joy. I received pictures of Joy and a text on how Joy was doing. This was my 1st time using Gail and I was very happy with her care for my fur bady. I would recommend Gail service and I definitely will be coming back to her. Thank you so much!!

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NaT H.
Sitter Profile Image: Omaira & Isaac Z.
Verified Enhanced Background Check
Omaira & Isaac Z.
from
$30
per night
5.0 out of 5 stars
139 reviews
32 repeat clients
20 years of experience
Newport News, VA, 23608

This is the 2nd time that Omaira and Isaac have taken care of my babies. Once again, they seemed very well taken care of. I felt guilty leaving them for so long, but they sent me many pics and videos of my dogs having fun to make me feel better. When I picked them up they looked very healthy. I can tell that they had a good experience at Omaira & Isaac's because when I took them out for a walk, they were more friendly with other people and dogs then they usually are. Even their grandma couldn't believe their good behavior! Thanks again guys!

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Catherine H.
Sitter Profile Image: Megan L.
Verified Enhanced Background Check
Megan L.
Star Sitter
from
$37
per night
5.0 out of 5 stars
106 reviews
43 repeat clients
5 years of experience
Portsmouth, VA, 23703

Megan took care of my Wilson for two weeks and I’m so thankful I found her! Her and her family took such good care of my boy and I was so appreciative of her daily updates and photos. Thank you Megan and we will see you again!

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Amy W.
Sitter Profile Image: Nathan & Alexandria B.
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Nathan & Alexandria B.
from
$40
per night
5.0 out of 5 stars
25 reviews
8 repeat clients
26 years of experience
Suffolk, VA, 23434

Nathan was amazing with our golden retriever, Rosie, while my family and I were away on a trip. He was incredibly attentive and caring throughout her stay, making it extra special with toys, space to play, and daily activities to keep her entertained. His kids loved her and took great care of her as well, which was so heartwarming. Nathan kept me updated daily with photos and messages, giving us peace of mind. I highly recommend Nathan to anyone looking for someone who will truly treat their pets like family!

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Kassandra R.
Sitter Profile Image: Chainey L.
Verified Enhanced Background Check
Chainey L.
Star Sitter
from
$26
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: Wesley "Whitney" B.
Verified Enhanced Background Check
Wesley "Whitney" B.
from
$50
per night
5.0 out of 5 stars
14 reviews
3 repeat clients
35 years of experience
Windsor, VA, 23487

Tremendous, my puppy Bryson got plenty of exercise and attention. Honestly I think he was happier here than at home. Wesley sent pictures of Bryson playing with her puppies, so I didn’t miss him too much. Highly recommend, will employ again.

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Dan S.
1 / 1
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Over 109
pet parents in Windsor have booked dog boarding

Windsor dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Rachel was absolutely amazing! I have never used Rover or a pet sitter before and she was so helpful, knowledgeable, and just genuinely nice. Milo was spoiled and loved and I got plenty of updates, she is great with communication. Will be using her again!

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Kimberly S.
Boarding
5.0 out of 5 stars

This is the second time that Rachel has kept our 2 dogs for a week. Rachel is very easy to communicate with and kept me updated throughout the week. We highly recommend Rachel and will continue to use her services in the future if the need arises!

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Kyle H.
Boarding
5.0 out of 5 stars

Rachel is great with Katie. Katie and her dogs got along well. Rachel is very helpful and provides lots of pictures and communication

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Carol F.
Boarding
1 / 1
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How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs 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 dog boarding in Windsor is $38

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 dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.

  • World-class support

    We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.

Sitters in Windsor average 9
repeat dog boarding clients

Dog Boarding FAQs

Frequently asked questions about Rover

As of Jun 2026, the median cost of dog boarding in Windsor is $38 per night, including service fees. Boarding your dog for one week typically costs $266. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Windsor dog boarding rates can be found as low as $31 to as high as $55 per night.

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

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

As of Jun 2026, 320 sitters provided dog boarding in Windsor. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple sitters about your booking. Typically, 96% of Windsor dog boarding sitters respond in under an hour.

Sitters who provide dog boarding in Windsor have an average of 16 years of experience. Dog boarding sitters with repeat customers have an average of 9 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Windsor.

Rover makes it easy to find Windsor dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:

  • Dogs of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their sitter’s pets

There are 320 dog boarding sitters in Windsor on Rover, so you’re sure to find the perfect match for your dog! In Windsor, 97% of sitters offer daily exercise, 100% offer medication administration, and 97% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your 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 dog boarding 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 dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.