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 M.
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Rachel M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
92 reviews
26 repeat clients
15 years of experience
Windsor, VA, 23487

Rachel took very good care of Fendi. She sent texts and pictures. Fendi has a new boyfriend! Her son! lol she was following him around. lol thanks for taking care of her. 😊

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cicely s.
Sitter Profile Image: Megan M.
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Megan M.
Star Sitter
from
$35
per night
5.0 out of 5 stars
14 reviews
2 repeat clients
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: Shelly S.
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Shelly S.
Star Sitter
from
$40
per night
5.0 out of 5 stars
184 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: 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 takes excellent care of Skipper. She communicates very well and always sends pictures. We are so happy that we found her, and Skipper is too!!

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

I had a last menu catering gig that I had to prepare and Vania came through. I appreciate you and your family with taking care of my baby boy Diezel while I was away handling business . It never goes unnoticed . If I could give 10 stars , I would . Be blessed , always . I highly recommend .

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Desiree D.
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
42 repeat clients
10 years of experience
Suffolk, VA, 23434

10 Stars ✨✨ This was Laila’s first stay with Melody and Matt and they took care of her like she was family. We look forward to her next visit.

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Carla H.
Sitter Profile Image: Abigail T.
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Abigail T.
from
$25
per night
4 years of experience
Windsor, VA, 23487

About: I have had dogs and cats in my life since i was a baby! They have always been my bestfriend! I currently have 1 dog (a golden retriever) and 2 cats. And I’ve house sat for many many fiends for long periods of time. In my eyes i don’t see them as just animals but another member to the family. And that’s how i would treat your fur babies! You should feel comfortable leaving your fur babies in the hands of someone else when life becomes busy or you just need to get away. and i promise I will give your babies all the love and attention they deserve! I work weekdays but i get off early almost everyday with very flexible hours and I’m off every weekend. My work schedule is pretty flexible. I have loads of free time! I have a fenced in yards. My dog is an inside dog (the house belongs to her lol) i have 2 cats that wants to sit on everyone lap. My dog has full access to the house when I’m home and only the downstairs when I’m gone. The cats roam the house as they please but they love to be by my side more than anything! My dog spends so much time outside playing and gets a long walk every day!

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 amazing with my Marley! This was my first time using Rover and I can admit I was a bit iffy about the app. Marley is 8 and has never stayed away from me, outside of my parents keeping her. I am very relieved and glad I found Rachel!! She sent lots of pictures and my mind was at ease for my trip!! Thank you thank you Rachel, Marley will definitely be hanging out again!!

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'Twinkie' A.
Sitter Profile Image: Wesley "Whitney" B.
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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

Wonderful sitter. Responded quickly which really helped me in an urgent situation. Sent tons of pics and I could tell my puppy had a ton of fun. Definitely recommended.

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Kyle M.
Sitter Profile Image: Omaira & Isaac Z.
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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

Prudence was very well taken care of by Omaira and Isaac! They are both very nice people and welcomed Prudence and us warmly when we arrived. I felt that she was safe and loved with them. The pictures made me smile as she looked relaxed and happy! I'd definitely leave her with them again and actually plan to do so!

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Jennifer N.
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

Betty (my corgi) & I both love Lisa and her family. It’s like her second home! So grateful for all the updates and pictures seeing how happy and loved she is while I’m away. ❤️

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Casey M.
Sitter Profile Image: Megan L.
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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 and her family were wonderful from beginning to end. Took loving care of our Marlowe and even helped us out in a pinch. Thank you again for your wonderful service. Will be booking again.

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

Julie and Kenny were awesome! They took the best care of my dog and she loved it there! They sent messages and pictures of her. My dog felt right at home in their place and they treated her like one of the family. She even slept with them at night in their bed! I will definitely have them watch Daisy again! :)

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Robin M.
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 and Alexandria are the best.. they are the only ones i trust to not only sit but love Star like their own. Can't thank them enough!!!!

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Evangelina J.
Sitter Profile Image: Milena B.
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Milena B.
Star Sitter
from
$40
per night
5.0 out of 5 stars
26 reviews
8 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: Lauryn B.
Verified Enhanced Background Check
Lauryn B.
Star Sitter
from
$30
per night
5.0 out of 5 stars
45 reviews
16 repeat clients
12 years of experience
Newport News, VA, 23608

Lauryn is a sweet, caring individual. I couldn't have asked for someone better!! She loved my girls and treated them like her own!! I got pictures and videos every day, which set my heart at ease. I will definitely use her again!! 🥰

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Laura H.
Sitter Profile Image: Amanda B.
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Amanda B.
from
$40
per night
4.9 out of 5 stars
17 reviews
8 repeat clients
30 years of experience
Suffolk, VA, 23434

Amanda loved on my two girls and they got along great with her pup! She sent some photos and updates and was flexible with our changing schedule. Her prices are reasonable, and you can tell she loves animals!

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Sarah H.
Sitter Profile Image: James C.
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James C.
from
$40
per night
4.9 out of 5 stars
49 reviews
14 repeat clients
15 years of experience
Suffolk, VA, 23438

Got pictures showing the girls were relaxed and comfortable. James is a good care giver, he is observant and patient. Definitely would book him again. Communication and timeframes worked out well. My girls have a couple quirks and frrom his feedback everything went well

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Lizabeth W.
Sitter Profile Image: Mckayla F.
Verified Enhanced Background Check
Mckayla F.
from
$35
per night
5.0 out of 5 stars
34 reviews
9 repeat clients
7 years of experience
Portsmouth, VA, 23702

McKayla was great with my two pugs! She sent pictures everyday and I know they had a great time. Will definitely go back to her for boarding again and highly recommend!

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Julia C.
Sitter Profile Image: Armonee H.
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Armonee H.
from
$20
per night
5.0 out of 5 stars
6 reviews
3 repeat clients
11 years of experience
Suffolk, VA, 23434

I can’t say enough good things about my experience with Armonee. My dogs first time with a boarder and she could not have made things easier for him and me. Her communication is top tier with regular texts, photos and concerns. She is caring, gentle and tailors her approach to fit the animals needs, like she did with my special needs senior dog. She treats pets like they are her own and it is obvious from the moment you meet her. I trusted her completely and will be rebooking with her in the future. Highly, highly recommend if you are looking for a safe and loving place for your pet. My dog came home happy, healthy, and clearly well cared for.

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Pamela D.
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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
5.0 out of 5 stars

Rachel was amazing, thoughtful, communicative with pictures of Egg throughout our trip. I highly recommend her as a Rover hire. Also, Rachel kept Egg active with her fenced in yard and when we picked her up she was happy and pooped!

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Alana B.
Boarding
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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.