Dog Boarding Windsor

Find a loving dog sitter to watch your dog overnight at your sitter's home.

Pick up
Search

Windsor, Find top rated dog boarding

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Michelle T.
Verified Enhanced Background Check
Michelle T.
Star Sitter
from
$40
per night
5.0 out of 5 stars
51 reviews
14 repeat clients
10 years of experience
Randolph, Richmond, VA, 23220

Michelle did a wonderful job watching our boy Remy! He can be very shy and nervous in new environments but Michelle made him feel right at home. Loved getting the updates and photos while we were out of town. Highly recommend and will book again :)

Profile image
Hannah O.
Sitter Profile Image: Michaela Z.
Verified Background Check
Michaela Z.
from
$45
per night
5.0 out of 5 stars
25 reviews
11 repeat clients
5 years of experience
Upper Shockoe Valley, Richmond, VA, 23223

Michaela was AMAZING! So sweet and attentive to Violet, and sent lots of updates and pictures throughout the stay, which gave us so much peace of mind. She administered Violet’s medications and special food three times a day with no issues and made everything feel effortless. Michaela was also very easy to schedule with and super responsive with communication. We’re so grateful to have found her and will definitely be booking with her again!

Profile image
Kayla E.
Sitter Profile Image: Myrna C.
Verified Enhanced Background Check
Myrna C.
Star Sitter
from
$41
per night
5.0 out of 5 stars
58 reviews
31 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!

Profile image
Daniel & Alisha S.
Sitter Profile Image: Aaren & Jordon D.
Verified Enhanced Background Check
Aaren & Jordon D.
Star Sitter
from
$45
per night
5.0 out of 5 stars
24 reviews
5 repeat clients
6 years of experience
Swansboro, Richmond, VA, 23224

Aaren and Jordan were such fabulous sitters for my itty bitty 80lbs pittie! They sent several pics and vids throughout his 2day stay which definitely put me as ease. Highly recommend!

Profile image
Sonia M.
Sitter Profile Image: Ross & Ava T.
Verified Enhanced Background Check
Ross & Ava T.
from
$40
per night
5.0 out of 5 stars
76 reviews
19 repeat clients
16 years of experience
Blackwell, Richmond, VA, 23224

Ross and Ava took great care of our old girl. They sent us updates regularly and were flexible on pick up time. We’ll definitely be booking with them again!

Profile image
Katelynn R.
Sitter Profile Image: Matt M.
Verified Enhanced Background Check
Matt M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
275 reviews
84 repeat clients
25 years of experience
Northern Barton Heights, Richmond, VA, 23222

I was so impressed with Matt! He sent updates and pics of my pups and they had a wonderful visit with him. We will definitely be booking with him whenever we stay in Richmond.

Profile image
Elaine R.
Sitter Profile Image: Hilary R.
Verified Background Check
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

Well, I just want to say they did wonderful with 2 dogs that have never had sitters before. They were so happy when I picked them up I knew they did a wonderful job. Unfortunately, one of my dogs is truly I'll, and they handled it wonderfully. Thanks guys. DOG has a vet appointment tomorrow and hopefully we have better enzyme results today. If not, I know they had great care. Thank you so much!

Profile image
Desiree K.
Sitter Profile Image: Raye J.
Verified Background Check
Raye J.
from
$46
per night
5.0 out of 5 stars
204 reviews
88 repeat clients
7 years of experience
Oakwood, Richmond, VA, 23223

Boarding with Raye was great! She was great with communication and making sure to send photos and videos every day. We've already rebooked with her!

Profile image
Lauren D.
Sitter Profile Image: Miguel A.
Verified Enhanced Background Check
Miguel A.
Star Sitter
from
$40
per night
4.9 out of 5 stars
41 reviews
11 repeat clients
7 years of experience
Henrico, VA, 23231

Great hosts! They were very accommodating and had a lovely home for Eddie. I also really appreciated the check in photos and videos to see that my dog was happy and safe. I will definitely book with them again

Profile image
Justin A.
Sitter Profile Image: Stacey M.
Verified Enhanced Background Check
Stacey M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
12 reviews
3 repeat clients
13 years of experience
Fulton, Richmond, VA, 23231

Stacey was the ultimate sitter and I couldn't have asked for a better first experience with Rover! She scheduled time for our dogs to meet in a public area first followed by a tour of her home and yard where Sebastian would be staying. I received photos of how much fun he was having while on my trip, and to be honest I bet he's looking forward to his next stay, what with having a four legged buddy and a wrap-around, fenced-in yard for unlimited zoomies. I can't recommend Stacey enough and will be sticking with her whenever it suits going forward.

Profile image
Lindsay Y.
Sitter Profile Image: Julie W.
Verified Enhanced Background Check
Julie W.
Star Sitter
from
$48
per night
5.0 out of 5 stars
73 reviews
14 repeat clients
30 years of experience
Carillon, Richmond, VA, 23221

Excellen all around! Great communication before and during our trip, with lots of consideration for the dogs’ routines and comfort. Loved all the photos that showed us the dogs were having a great time at “camp” — knowing they were in good hands let us enjoy our trip all the more. Wouldn’t hesitate to book again.

Profile image
Joanna D.
Sitter Profile Image: Kendra B.
Verified Enhanced Background Check
Kendra B.
Star Sitter
from
$25
per night
5.0 out of 5 stars
41 reviews
11 repeat clients
25 years of experience
North Chesterfield, VA, 23237

Kendra was amazing with Tinkerbell. She kept us updated each day which put our mind at ease with this being our first time using Rover. The pictures where the best as we could see in real time how well she was being cared for. Thank you Kendra!

Profile image
Tracy T.
Sitter Profile Image: DAMACIA J.
Verified Enhanced Background Check
DAMACIA J.
Star Sitter
from
$28
per night
5.0 out of 5 stars
318 reviews
86 repeat clients
30 years of experience
North Chesterfield, VA, 23236

I am more than pleased with the ❤️ and care DAMACIA provided for my 3 months puppy. I would recommend her and we will be going back. Was a little nervous at first, but she reassured me he would be fine even around other Fur Babies.

Profile image
Cheryl B.
Sitter Profile Image: Tiffany B.
Verified Enhanced Background Check
Tiffany B.
Star Sitter
from
$49
per night
5.0 out of 5 stars
17 reviews
7 repeat clients
20 years of experience
Swansboro, Richmond, VA, 23225

Tiffany was awesome, she took Roxie very last minute with open arms. She sent me pictures throughout the duration & kept me updated. I felt very comfortable & will definitely be back.

Profile image
Tana J.
Sitter Profile Image: Deven & Tyreek C.
Verified Enhanced Background Check
Deven & Tyreek C.
Star Sitter
from
$40
per night
5.0 out of 5 stars
27 reviews
13 repeat clients
15 years of experience
North Chestefield, VA, 23237

We had an amazing experience boarding our dog with Deven and Tyreek from start to finish! They treated Riot just like their own; he was happy, comfortable and loved! Their communication was excellent, especially the frequent updates they sent with pictures and videos to show us how much fun Riot was having. We (Riot included) are grateful for the care they provided and would absolutely book them again in the future!!

Profile image
Tenae W.
Sitter Profile Image: Emily H.
Verified Enhanced Background Check
Emily H.
Star Sitter
from
$48
per night
5.0 out of 5 stars
134 reviews
57 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!

Profile image
Renée C.
Sitter Profile Image: Elizabeth H.
Verified Enhanced Background Check
Elizabeth H.
from
$35
per night
5.0 out of 5 stars
11 reviews
20 years of experience
Westlake Hills, Richmond, VA, 23225

Libby was a lifesaver for us. She took care of our geriatric Golden for three days while we were away, then stepped up for an additional four days at the last moment due a a medical emergency, even buying addition food and supplements as needed. She is clearly a dog lover, and our Golden was very comfortable and well cared for with her and her two dogs. Excellent communication and lots of photos completely set our minds at ease at a time when we didn’t need any additional worries. We even got a thorough report-card and little polaroid of our Golden when we picked her up. I can’t say enough good things about Libby. Your dog would be very lucky to have her as a sitter.

Profile image
Daniel L.
Sitter Profile Image: Abby M.
Verified Background Check
Abby M.
Star Sitter
from
$38
per night
5.0 out of 5 stars
282 reviews
98 repeat clients
14 years of experience
Chester, VA, 23831

Abby was a wonderful sitter for my two large Dobermans. The oldest has cancer and the youngest, I admit, is a spoiled handful. Abby was knowledgeable in the handling of both. I recommend her highly.

Profile image
Olyn W.
Sitter Profile Image: Kristine H.
Verified Enhanced Background Check
Kristine H.
from
$43
per night
5.0 out of 5 stars
3 reviews
20 years of experience
Central Office, Richmond, VA, 23219

Kristine was fantastic! Reliable and great communication. Loved the photo updates. Cats are very relaxed and happy. Would not hesitate to book again!

Profile image
Jane P.
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 was fantastic! She sent updates and pictures everyday. Nellie had the most fun with Laura and her family. I loved how they really adopted Nellie into the family for the week!

Profile image
Natasha S.
1 / 1
View more sitters

The median cost per night for dog boarding in Windsor is $45

Dog parents share their Rover experiences - Windsor

1 / 1
5.0 out of 5 stars

Raven did an amazing job watching my dog! She took the best pictures! When I picked up my dog and put her in the car to go home, she put her paws up on the seat and looked back longingly at Raven’s house as we drove away like she didn’t want to leave!

Profile image
Ryan J.
Boarding
5.0 out of 5 stars

Booked last minute with Tiffany B. she accepted my Pup and also taught her some manners In the process lol. Overall experience was great, I will definitely be rebooking.

Profile image
Jason K.
Boarding
5.0 out of 5 stars

Ross and Ava are fabulous sitters! This was my dog’s first time staying with them and their sweet dog, George, and I was wondering if Reggie would want to come home with me after being taken care of so well! 😊 Ross & Ava were great with providing updates and also being mindful of the heat for walks. Finding a sitter can be such a stressful process but Ross & Ava were great with coordinating a meet and greet beforehand and putting my mind at ease. Your pet will be in great hands!

Profile image
Andrea M.
Boarding
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.

Profile image
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 !

Profile image
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.

Profile image
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!

Profile image
Savannah L.
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! !

Profile image
Deborah R.
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!!

Profile image
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.

Profile image
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!

Profile image
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!

Profile image
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!

Profile image
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.

Profile image
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.

Profile image
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.

Profile image
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.

Profile image
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!

Profile image
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.

Profile image
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.

Profile image
Jake M.
Boarding
1 / 1
Find pet care near you

Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 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.

How Rover works

  1. 1. Search

    Browse profiles of sitters near you who offer dog boarding
  2. 2. Meet & Greet

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Sitters in Windsor average 12
repeat dog boarding clients

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge