Dog Boarding In Windsor

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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: Michelle T.
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Michelle T.
Star Sitter
from
$40
per night
5.0 out of 5 stars
49 reviews
13 repeat clients
10 years of experience
Randolph, Richmond, VA, 23220

Mich was awesome! Our dog felt welcomed and comfortable during her stay. Mich’s dog, Milo, was a good companion/ host. Great back yard. Mich sent pictures and regular updates. Couldn’t have asked for a better experience.

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Michael G.
Sitter Profile Image: Aaren & Jordon D.
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Aaren & Jordon D.
Star Sitter
from
$45
per night
5.0 out of 5 stars
22 reviews
5 repeat clients
6 years of experience
Swansboro, Richmond, VA, 23224

Aaren and Jordan are absolutely amazing, phenomenal pet sitters! From the moment I left Arya in their care, I knew she was in loving and patient hands. They treated her like family, and that meant everything to me while I was away. Their communication was top-tier—they kept me updated consistently with messages and check-ins, which gave me so much peace of mind. On top of that, they were incredibly flexible and accommodating, making the whole experience smooth and stress-free. Arya truly found her second home with them, and there’s no doubt they are now her permanent sitters. I appreciate them more than words can express and can’t thank them enough for the love and care they showed my big girl. 💕🐾

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Brittney T.
Sitter Profile Image: Myrna C.
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Myrna C.
Star Sitter
from
$41
per night
5.0 out of 5 stars
54 reviews
30 repeat clients
40 years of experience
Oakwood, Richmond, VA, 23223

Myrna was great with our dog Archie!! She's very experienced with watching dogs and her house seems like a great environment for dogs to have a great time. I'd highly recommend her!

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Daniel & Alisha S.
Sitter Profile Image: Michaela Z.
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Michaela Z.
from
$45
per night
5.0 out of 5 stars
23 reviews
11 repeat clients
5 years of experience
Upper Shockoe Valley, Richmond, VA, 23223

Michaela was absolutely fantastic with Zephyr and it was so clear he had such a great time with her this weekend! During our stay she sent tons of pictures to keep me updated on what Zeph was up to and was very communicative throughout the whole rover process. We met ahead of time during a meet and greet where Zeph got tons of time to get to know his new aunt Michaela and vice versa and it was clear to see how great she was with handling him from the start. We will absolutely be back and are so happy to have met you! Thanks so much for taking such great care of Zephyr!

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Sindhu S.
Sitter Profile Image: Matt M.
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Matt M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
266 reviews
84 repeat clients
25 years of experience
Northern Barton Heights, Richmond, VA, 23222

Matt was absolutely wonderful our Dalmatian, Juniper! He was also so accommodating when our flight home was cancelled resulting in us picking her up a couple hours later than originally scheduled. I would highly recommend him if you ever need a sitter for your dog, and would not hesitate to book with him in the future.

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Jared M.
Sitter Profile Image: Ross & Ava T.
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Ross & Ava T.
from
$38
per night
5.0 out of 5 stars
74 reviews
19 repeat clients
16 years of experience
Blackwell, Richmond, VA, 23224

Alice came home from a long stay happy, relaxed, and waggy. Grateful to Ross and Ava for their thoughtful care, communication, flexibility, and laid back orientation. We (and by we, I do mean Alice…) will be back!

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Zoe & David C.
Sitter Profile Image: Hilary R.
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Hilary R.
Star Sitter
from
$38
per night
5.0 out of 5 stars
217 reviews
73 repeat clients
20 years of experience
Reedy Creek, RICHMOND, VA, 23225

Hillary was absolutely wonderful watching my pup Zephyr for the day. She sent pictures while Zeph was staying with her and kept me updated on details regarding how he was adjusting and feeling while in her care. It was clear to see how much she cared and prioritized my pups comfort over everything. We will absolutely be coming back and I look forward to zeph staying here again!!! :)

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Sindhu S.
Sitter Profile Image: Stacey M.
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Stacey M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
11 reviews
3 repeat clients
13 years of experience
Fulton, Richmond, VA, 23231

Stacey is so great with my Puppy Poppy! We are still crate, potty and puppy manner training and she was able to keep up with training while we were away. I loved getting updates and pictures throughout the weekend and even was able to keep her an extra night because we were stuck in traffic and wouldn’t get back until later than expected. Poppy had a wonderful time and says she can’t wait until her next stay with her new friends!

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Jessica R.
Sitter Profile Image: Raye J.
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Raye J.
from
$46
per night
5.0 out of 5 stars
200 reviews
86 repeat clients
7 years of experience
Oakwood, Richmond, VA, 23223

I so appreciate the time Chip spent with Raye ! She took him on walks and integrated him into the dog pack very thoughtfully. Lots of pictures and videos!

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Christine D.
Sitter Profile Image: Miguel A.
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Miguel A.
Star Sitter
from
$40
per night
4.9 out of 5 stars
39 reviews
11 repeat clients
7 years of experience
Henrico, VA, 23231

Pretzel had a great time! She got lots of attention and playtime and came home and immediately went to sleep because she was so exhausted from all her fun.

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David B.
Sitter Profile Image: Alexandra O.
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Alexandra O.
from
$45
per night
5.0 out of 5 stars
71 reviews
24 repeat clients
15 years of experience
Westover Hills, Richmond, VA, 23225

Dewi and I have had a wonderful first experience boarding with Alex! I was out of the country for two weeks, but always could tell form the updates, photos and videos that my gentle old man was in the best of care. Especially loved seeing him get special attention on his 15th birthday! Alex has much experience with all types of dogs, and it shows. Very professional. Thank you so much!

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Elizabeth K.
Sitter Profile Image: Kendra B.
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Kendra B.
Star Sitter
from
$25
per night
5.0 out of 5 stars
38 reviews
8 repeat clients
25 years of experience
North Chesterfield, VA, 23237

Kendra did amazing Niko!! She let us know how he did every single day with a detailed explanation which made me feel super comfortable. She kept my mind at ease. Will forever be going to Kendra ❤️

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Dahlia & Jalen B.
Sitter Profile Image: DAMACIA J.
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DAMACIA J.
Star Sitter
from
$28
per night
5.0 out of 5 stars
315 reviews
84 repeat clients
30 years of experience
North Chesterfield, VA, 23236

Highly recommend. Damacia took care of Teddy very well.. Teddy attached to her as a family member. She updated every day with his picture. Thanks Damacia 🥰

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Alwin R.
Sitter Profile Image: Julie W.
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Julie W.
Star Sitter
from
$48
per night
5.0 out of 5 stars
70 reviews
12 repeat clients
30 years of experience
Carillon, Richmond, VA, 23221

Julie is awesome! She went way above and beyond what I expected and made huge efforts to make Ginger (my high-energy Harrier) comfortable in her home. I love that she used positive reinforcement to keep Ginger inline instead of negative feedback. Ginger even escaped from her house and thank goodness Julie was able to call her back. Julie sent tons of updates via video and pictures keeping me well informed of everything going on during her stay. Ginger had ZERO separation anxiety when I picked her up and brought her back to my house. She normally has very extreme separation anxiety and I was out of town for a long time, so this was a HUGE relief for me (and Ginger I imagine as well!) Having Ginger stay in a loving home environment was so much better for her than the typical dog boarding environments. I feel like I picked up Ginger from an extended sleepover, not an exity filled environment typical to boarding. I highly recommend Julie to watch your pet!!! Your little one will feel so loved and welcomed. Julie is awesome!!!

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Liz F.
Sitter Profile Image: Emily H.
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Emily H.
Star Sitter
from
$48
per night
5.0 out of 5 stars
130 reviews
56 repeat clients
6 years of experience
Chimborazo, Richmond, VA, 23223

I feel so confident taking my older dogs to Emily. I know she'll give them lots of love and make sure they're comfortable and content. So happy to have found her!

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Renée C.
Sitter Profile Image: Nadia J.
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Nadia J.
Star Sitter
from
$60
per night
5.0 out of 5 stars
32 reviews
14 repeat clients
10 years of experience
Randolph, Richmond, VA, 23220

Nadia took great care of my 11-year-old dog Nike. She sent pictures every day of her activity and my dog seems so happy to be among other dogs, which was surprising to me. I would definitely use her again. Nike was in good hands the entire time.

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Pamela B.
Sitter Profile Image: ashley g.
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ashley g.
from
$26
per night
5.0 out of 5 stars
29 reviews
10 repeat clients
7 years of experience
Oak Grove, richmond, VA, 23224

Ashley was absolutely amazing with Onyx over the Christmas and New Year’s holiday! She kept me updated with pictures and messages throughout my time away, which gave me so much peace of mind. Onyx loved playing with her kids and looked so adorable cuddling with everyone, it was clear he felt right at home. When Onyx struggled a bit at night and was barking, Ashley was incredibly patient and kind. She reached out to ask for advice and even allowed calming treats to be dropped off while I was away, which I truly appreciated. She followed all of my special instructions perfectly, including giving him his Christmas presents on Christmas Day and feeding him a special holiday meal. I’m so grateful for the love and care she showed Onyx and would absolutely trust her again. Highly recommend Ashley to anyone looking for a reliable, compassionate sitter!

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Keyira F.
Sitter Profile Image: Jeffrey H.
Verified Enhanced Background Check
Jeffrey H.
Star Sitter
from
$33
per night
5.0 out of 5 stars
94 reviews
22 repeat clients
34 years of experience
The Fan, Richmond, VA, 23220

Jeremy took care of my dog Parker while I was out of the country for a week. I felt Parker was in excellent hands and seemed happy and rested when I got back! Jeremy was super communicative leading up to Parker’s stay as well as during it sending lots of fun videos of their strolls around the neighborhood. Would definitely use Jeremy again!

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Keri L.
Sitter Profile Image: Elexiss A.
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Elexiss A.
from
$40
per night
7 years of experience
Richmond, VA, 23224

About: Although I don't have a pup of my own , I've loved dogs since I could walk! My grandmother and Aunt always kept their dogs around me and they became my best friends. Over the years I've cared for the pups of my friends and family. I currently work full time as a Licensed massage therapist. Weekdays are my busiest and weekends are typically when I'm free the most. I’m the perfect person to take care of your pups during your weekend getaways! I live on Bainbridge st but I know of plenty of safe spaces and trails to walk nearby. My apartment is dog friendly and I will have plenty of places to walk and play with your pup. I don't have any children or other pets , so your pet will get all my love and attention!

Sitter Profile Image: Laura C.
Verified Enhanced Background Check
Laura C.
Star Sitter
from
$28
per night
5.0 out of 5 stars
8 reviews
2 repeat clients
16 years of experience
Richmond, VA, 23236

Laura had my dog nova for a week.Great with keeping you updated on your pet.Nova had a blast will definitely use Laura again.My dog was sad to go home that’s how much fun she had

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Wini P.
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Windsor dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Amazing stay! Our girl Logan had the best weekend. Would recommend to anyone needing a dog sitter in RVA.

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Jake L.
Boarding
5.0 out of 5 stars

Allison is the best! This is the second time we’ve used her and she’s nothing short of wonderful. She lives on our baby like they’re her own and she updated us so consistently that we felt like he was with us. I’ve used sooo many dogsitters in the past having had dogs my whole life & none compare to her level of service !

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Madison R.
Boarding
5.0 out of 5 stars

Myrna was great with my pup. Super responsive, lots of great pictures, and I don’t think my dog wanted to leave! Highly recommend.

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Aidan M.
Boarding
5.0 out of 5 stars

Zach was great! He made sure Hank got plenty of love and exercise! Hank’s extra needy but they seemed to have a great time. Thank you!

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Savannah L.
Boarding
5.0 out of 5 stars

Decker had so much fun staying with Raye! She loves other dogs and they provided a safe place for her to play all day. We received plenty of pictures and updates and she came home a tired, happy pup.

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Brittany Y.
Boarding
5.0 out of 5 stars

Lilly took good care of Luca! She texted me with updates and photos every day. Highly recommend Lilly! !

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Deborah R.
Boarding
5.0 out of 5 stars

Ross was kind and communicative during my dog’s stay. My dog seemed comfortable there, and I think she got along well with George. Pickup and drop off were smooth, and overall it was a positive experience.

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Maria M.
Boarding
5.0 out of 5 stars

We are so grateful for all the love Aaren & Jordon gave to Dexter while we were out of town! They treated Dex like he was their own and we feel so lucky to have found them. 10/10 recommend!!

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Jen R.
Boarding
5.0 out of 5 stars

Bauer had a great time and Emily was an amazing caretaker - we couldn't recommend her more. Simply A+ at every level and kept us informed with pictures and notes daily.

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Joseph Z.
Boarding
5.0 out of 5 stars

Hilary was great! She sent pictures and updates and Annie came back home happy. We will definitely use her again!

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Ellen T.
Boarding
5.0 out of 5 stars

Kaitlyn is a great sitter! Cash loved her and felt right at home with her. She sent me lots of pictures and was responsive when I wanted to check in. I will book her again!

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Brittney H.
Boarding
5.0 out of 5 stars

Christine was Great! Franci had smiles on all of her pictures and seemed to have a lot of fun! Thanks Christine!

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Sandra F.
Boarding
5.0 out of 5 stars

Morgan was amazing, and it seems like Ruby had so much fun with her and her dog. Morgan sent plenty of pictures and updates. She was very understanding and communicative when I had stressful return flight delays and cancellations. I’ll definitely rebook her next time I travel and need to leave my pup behind.

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Lindsay M.
Boarding
5.0 out of 5 stars

Great sitters. They took excellent care of my senior dog, kept me informed, and clearly cared about my pet. Highly recommend.

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shari g.
Boarding
5.0 out of 5 stars

I knew during the drop off that my Cocoa would be well taken care of and I was not disappointed. She also gained some new friends.

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Sabrina H.
Boarding
5.0 out of 5 stars

Taylor is a great sitter! She took great care of Diego and provided plenty of updates when we were out of town.

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Claire H.
Boarding
5.0 out of 5 stars

Ashley was absolutely amazing with Onyx over the Christmas and New Year’s holiday! She kept me updated with pictures and messages throughout my time away, which gave me so much peace of mind. Onyx loved playing with her kids and looked so adorable cuddling with everyone, it was clear he felt right at home. When Onyx struggled a bit at night and was barking, Ashley was incredibly patient and kind. She reached out to ask for advice and even allowed calming treats to be dropped off while I was away, which I truly appreciated. She followed all of my special instructions perfectly, including giving him his Christmas presents on Christmas Day and feeding him a special holiday meal. I’m so grateful for the love and care she showed Onyx and would absolutely trust her again. Highly recommend Ashley to anyone looking for a reliable, compassionate sitter!

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Keyira F.
Boarding
5.0 out of 5 stars

Evie was understanding when we had to cut our trip short, shortening the boarding time needed. She was flexible as I notified her on a daily basis that we would not be starting that day. When we dropped Brady off, we were happy to see that Evie lives in a well kept house in a safe neighborhood. She took really good care of Brady, giving him daily supplements, feeding him twice a day and taking him out for walks and plenty of bathroom breaks. Brady even got along with her friendly dog, named Cupid. She shared photos and a video of them playing. She's among the best boarders we've had on Rover.

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Sunil T.
Boarding
5.0 out of 5 stars

Ramiza is our go to! She is responsive, flexible, and extremely understanding! I cannot recommend her enough for care for your pets.

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Jake M.
Boarding
5.0 out of 5 stars

Thank you so much for watching Jesse! I received prompt responses and lots of photos and Jesse seemed to really enjoy his time with Madison and Winnie!

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Pauline A.
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!

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.

Dog Boarding FAQs

Frequently asked questions about Rover

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.

Typically, dog boarding sitters on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your dog in no time!

Experience can vary widely from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when comparing sitters available 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

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.