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: Kendra B.
Verified Enhanced Background Check
Kendra B.
Star Sitter
from
$25
per night
5.0 out of 5 stars
48 reviews
12 repeat clients
25 years of experience
North Chesterfield, VA, 23237

Kendra was great! This was Yasha’s second time staying with her in less than a month. Goes to show how reliable she is and how comfortable she makes you feel, leaving your fur baby with her. She truly cares. I appreciate all the photo’s and updates as well. It’s good to know my baby is having a good time while I am vacationing. No more guilt! lol

Profile image
Tawana B.
Sitter Profile Image: Ayme Z.
Verified Background Check
Ayme Z.
Star Sitter
from
$50
per night
5.0 out of 5 stars
606 reviews
176 repeat clients
12 years of experience
Oak Grove, Richmond, VA, 23224

Ayme was great. She came highly recommended and for good reason. We felt very comfortable leaving our dog with her and knew he was in good hands. She was responsive and sent photos of our dog throughout the weekend. Would recommend!

Profile image
Nadia S.
Sitter Profile Image: Eric J.
Verified Enhanced Background Check
Eric J.
from
$26
per night
5.0 out of 5 stars
1 review
1 repeat client
10 years of experience
The Diamond, Richmond, VA, 23220

Eric is the best! I recently had a sitter cancel 6 hours before drop-off -- I thought my vacation was ruined! I immediately put out a Sunday morning last-minute Rover requests for a sitter, with very low expectations that anyone would even respond, much less accept. Within a few minutes, Eric responded and then accepted. He totally saved my vacation! After that, he was extremely communicative, but even better, he was perfect for my highly energetic doggo. He gave long dauly walks and play sessions. I knew that my dog would love having his Bucky as a 24/7 playmate, but I was very concerned that he has cats, since Sheba had never seen a cat before. Since she has a high prey drive, I thought there could be serious problems. Eric, however, seems to have a natural understanding of pets, and he was able to safely introduce Sheba to his cats, and apparently there were no issues. Also, Eric was highly flexible when my return flight was delayed by a day, and quickly agreed to extend the stay. I couldn't have asked for a better experience from start to finish.

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

Matt’s place is my girls favorite place! They get the backyard, the cozy home, and all the friends they could hope for!! They don’t want to come home! Thanks for taking such great care of my crazy girls!

Profile image
Brooke N.
Sitter Profile Image: Michelle T.
Verified Enhanced Background Check
Michelle T.
Star Sitter
from
$40
per night
5.0 out of 5 stars
54 reviews
15 repeat clients
10 years of experience
Randolph, Richmond, VA, 23220

Michelle always does a great job sitting my dog. I had a last minute trip planned and she was able to accommodate. I even had a delayed trip back home and she was very flexible which I appreciated.

Profile image
Chelsy H.
Sitter Profile Image: Jay B.
Verified Background Check
Jay B.
Star Sitter
from
$39
per night
5.0 out of 5 stars
316 reviews
102 repeat clients
30 years of experience
Henrico, VA, 23231

Jay is so great! Left my 5 year old, super energetic lab mix with her and she handled him beautifully! I always worry that he will overwhelm people with his high energy... but Jay had no issues, and I had pictures and updates regularly throughout the entire stay!

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

During July 4th, we planned on going out of town for the weekend. We were impressed with Julie's rover profile and decided to contact her. We were able to meet up with her twice, once so that she could see our dog, and the second time so that Mozzie could check out her place. This was the first time since adopting him over a year ago that were had ever boarded him somewhere, so we were understandably nervous about it, but Julie proved to be a great sitter. She sent us status updates and pictures while we were away, so that we could know what Mozzie was up to. When we came to pick him up, she also helped us with tips and ideas on how to help Mozzie socialize with other dogs. We could definitely tell that Mozzie was in good hands. Definitely recommended!

Profile image
Kathy S.
Sitter Profile Image: Tiffany B.
Verified Enhanced Background Check
Tiffany B.
Star Sitter
from
$50
per night
5.0 out of 5 stars
19 reviews
7 repeat clients
20 years of experience
Swansboro, Richmond, VA, 23225

Tiffany is amazing! This was the first time I boarded my Simba. I was so nervous. However, Simba was very well taken care of. Tiffany kept me updated with texts and pictures. She was professional and caring toward not only Simba but me as well. Simba truly enjoyed his stay. I don’t think he wanted to come home! I will definitely use Tiffany’s services again. If you want a reliable, patient, caring, and professional person to care for your pet, Tiffany is your person!!!

Profile image
Jewel K.
Sitter Profile Image: Dylan H.
Verified Enhanced Background Check
Dylan H.
Star Sitter
from
$40
per night
5.0 out of 5 stars
558 reviews
207 repeat clients
20 years of experience
Chester, VA, 23831

Do not hesitate to book with Dylan and Alex! You will not regret it. It is such a blessing to find someone who will take care of your babies while you’re away. I knew that Lucy was in great hands and it gave me the peace of mind that I needed while I was away. Lucy had such a wonderful time and was completely exhausted from all of the play time. I am going to make Dylan and Alex my official boarding for all of my trips planned until December. Thank you gentlemen!

Profile image
Annette M.
Sitter Profile Image: Hilary R.
Verified Background Check
Hilary R.
Star Sitter
from
$38
per night
5.0 out of 5 stars
219 reviews
75 repeat clients
20 years of experience
Reedy Creek, RICHMOND, VA, 23225

Hilary and her family took great care of our pup for a 10 day stay while my husband and I were traveling. We received daily pictures and messages, so we knew how our pup was doing. We will definitely book again!

Profile image
Idris S.
Sitter Profile Image: Amy M.
Verified Background Check
Amy M.
Star Sitter
from
$35
per night
5.0 out of 5 stars
587 reviews
231 repeat clients
6 years of experience
Glen Allen, VA, 23060

Amy was great, she kept me informed and sent me daily pictures, my dogs always looked happy , they had a great time, and met new friends! Thank you so much Amy!

Profile image
Laura S.
Sitter Profile Image: DAMACIA J.
Verified Enhanced Background Check
DAMACIA J.
Star Sitter
from
$28
per night
5.0 out of 5 stars
326 reviews
90 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 🥰

Profile image
Alwin R.
Sitter Profile Image: Cindy T.
Verified Enhanced Background Check
Cindy T.
from
$42
per night
5.0 out of 5 stars
311 reviews
84 repeat clients
20 years of experience
north chesterfield, VA, 23235

Cindy was amazing at caring for my two dogs, Loki and Tashi. Dogs have a sixth sense of humans and as soon as they entered her home they were excited and happy. Cindy sent us photos of our dogs which was an adorable touch. For once, my husband and I were relaxed and were able to enjoy our outing without worrying about our dogs. We were disappointed that our dogs were not that excited to see us when we picked them up. That meant they had a great time at Cindy's. So much so that they crashed shortly after we got home. They were exhausted from their exciting day with Cindy and her adorable daughter. We are so delighted to have found Cindy.

Profile image
Midori H.
Sitter Profile Image: Zach K.
Verified Background Check
Zach K.
from
$45
per night
5.0 out of 5 stars
11 reviews
4 repeat clients
9 years of experience
Reedy Creek, Richmond, VA, 23225

First time having my dog watched by Zach he did everything I asked of him and more and on top of that was extremely friendly and kind! My dog had an accident or two didn't, cause a issue about it while I was for business I would definitely recommend leaving your dog with him

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

This was my first time leaving my dog at someone's house and he LOVED his time with Raye and Ollie! Raye sent me pics throughout his stay and took him on some adventures! I will definitely be using her again, thanks Raye!!

Profile image
Anne M.
Sitter Profile Image: Donetta N.
Verified Enhanced Background Check
Donetta N.
Star Sitter
from
$50
per night
5.0 out of 5 stars
71 reviews
14 repeat clients
10 years of experience
Richmond, VA, 23223

Donetta is the absolute best! She provided regular updates with photos over the course of my pup’s stay. She creates an environment that made my pup feel right at home. I could tell that Fiona had a great time because she came home completely exhausted. Donetta was also flexible when I needed to extend the reservation and additional night. Thank you so much. Highly recommend! Will definitely book again!

Profile image
Dominique W.
Sitter Profile Image: Sheri J.
Verified Background Check
Sheri J.
from
$40
per night
5.0 out of 5 stars
100 reviews
31 repeat clients
7 years of experience
Richmond, VA, 23229

Sherri is very caring and honest. I was happy that Maggie was in good hands for 1 1/2 days. Highly recommended. She has a heart of an angel. I am disappointed that she is moving to another state.

Profile image
anna r.
Sitter Profile Image: Dawn B.
Verified Enhanced Background Check
Dawn B.
Star Sitter
from
$44
per night
5.0 out of 5 stars
264 reviews
90 repeat clients
20 years of experience
Huguenot, Richmond, VA, 23235

Dawn was fantastic! She was very responsive and accommodating to our moving schedule. Sent lots of updates and photos. Jackson came home happy and enjoyed his stay.

Profile image
Lisa P.
Sitter Profile Image: Abby M.
Verified Background Check
Abby M.
Star Sitter
from
$40
per night
5.0 out of 5 stars
293 reviews
106 repeat clients
14 years of experience
Chester, VA, 23831

Abby was accommodating for a meet and greet, which I greatly appreciated; Oliver gets scared when I drop her off to stay with a stranger. Abby provided daily pictures and updates on how Oliver was doing and she came back very happy. I would use Abby again to pet sit.

Profile image
Emily B.
Sitter Profile Image: Kourtney D.
Verified Enhanced Background Check
Kourtney D.
Star Sitter
from
$45
per night
5.0 out of 5 stars
90 reviews
20 repeat clients
17 years of experience
North Chesterfield, VA, 23234

Kourtney was awesome with our baby girl Daisy Mae! We were pretty nervous because Daisy is just under 2 years old and had never been boarded or babysat. Kourtney was great, providing updates every day and we can tell Daisy was well taken care of. Thanks Kourtney!

Profile image
Kris M.
1 / 1
View more

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

Triston watched over our two dogs while we went on vacation for a week and we couldn’t be more pleased with the experience we had! Triston has a genuine compassion towards animals that we immediately felt when meeting him. He preferred knowing daily habits and schedules which we really appreciated. We will definitely be reaching back out to Triston again in the future!

Profile image
Spenser C.
Boarding
5.0 out of 5 stars

Aaren and Jordon were great! Very communicative throughout the week and pepper was very well taken care of!!

Profile image
Andrew K.
Boarding
5.0 out of 5 stars

Chris was patient with my Rottie, especially since he’d only stayed with a boarder before. He adjusted when my dog wasn’t eating normally, which I really appreciated. The photo updates from their walks showed how happy and comfortable he was.

Profile image
Martina T.
Boarding
5.0 out of 5 stars

Raye is a dog whisperer! She was a wonderful caretaker for our elderly companion. Our dog rarely switches his scenery up outside of our home so it was comforting seeing him adjust so easily with Raye - who ensured his safety and comforbitjty including a few extra needs of his because of his age. We received daily updates and was able to enjoy our time away while our dog enjoyed new friends at Rayes house. We give doggy adventures above 5 stars and will be back again. Thank you!

Profile image
Elena M.
Boarding
5.0 out of 5 stars

I couldn’t have asked for a better dog sitter! From the very beginning, I felt completely confident that my dog was in loving and capable hands. Tiffany provided excellent care, attention, and affection, and it was clear that my dog was happy, comfortable, and well cared for. She was reliable, responsible, communicative, and attentive to every detail. I especially appreciated the updates and knowing that my dog was being treated like family while I was away. Her genuine love for animals really showed. I highly recommend her to anyone looking for someone they can trust completely with their beloved pet. I will definitely use her again! 🐾❤️ Thank you for taking such wonderful care of my fur baby!

Profile image
Grace T.
Boarding
5.0 out of 5 stars

As always, the absolute best. Ross and Ava take wonderful care of Layla whether it’s a last minute booking or far in advanced. HIGHLY RECOMMEND

Profile image
Whodey A.
Boarding
5.0 out of 5 stars

Myrna took great care of our dog and he seemed very happy. He had lots of outdoor time and went to the dog park.

Profile image
Tess P.
Boarding
5.0 out of 5 stars

Lilly was attentive, sweet, and communicative. She was also super flexible when we had to adjust our pick up time. Our pup deals with some anxiety so having someone who could make her feel comfortable was a huge plus! Would gladly book with Lilly again!!!

Profile image
Susana B.
Boarding
5.0 out of 5 stars

Hilary and her family were very kind with our pup. They walked him everyday, sometimes two or three times a day. Hilary is communicative and followed our directions for our dog. We were on vacation for a week and she sent photos and videos.

Profile image
Jennifer Lee N.
Boarding
5.0 out of 5 stars

Ashley came through with a last minute request for our puppy. Really appreciate the communication before and during the stay, and pics! Our puppy had some particular needs (as all puppies do) and she took really good care of her. Thanks so much Ashley!!!

Profile image
Amzi J.
Boarding
5.0 out of 5 stars

Morgan has taken care of my pup multiple times now, and each time she comes back very happy and healthy. Morgan is kind, responsible, trustworthy, and provides so many updates! I would 100% ask her to watch my pup in the future.

Profile image
Lindsay M.
Boarding
5.0 out of 5 stars

Noel was amazing to work with! She responded quickly after a rover cancelled. We got a quick meet in and greet in and it was perfect! Her home has a nice back yard and her and her boyfriend provided so much love and attention! Great people and a beautiful home, can’t recommend enough.

Profile image
Joshua K.
Boarding
5.0 out of 5 stars

Even though there was no meet and greet jasmine was perfect with honey. I’m happy she was able to take my request last minute and she took cute pictures of my girl :) overall great sitter and provides constant updates.

Profile image
Patricia L.
Boarding
5.0 out of 5 stars

Gaelle took wonderful care of Oakland while I was away! Oakland was feeling a bit under the weather from anxiety leading up to my trip, and Gaelle was incredibly attentive, keeping a close eye on her and sending regular updates and photos that gave me so much peace of mind. Thankfully, Oakland's stomach settled, and it was clear she was in great hands throughout her stay. I really appreciated the care, communication, and kindness Gaelle showed. I wouldn't hesitate to book with her again and would absolutely recommend her to anyone looking for a trustworthy sitter!

Profile image
Brittney R.
Boarding
5.0 out of 5 stars

Veggie had a great time and was taken good care of by Kristine for a week when I was on vacation. Kristine was responsive and sent me pictures of Veggie when I missed her.

Profile image
Yang X.
Boarding
5.0 out of 5 stars

Emily was excellent! She sent me daily updates, pictures, and was super patient and accommodating for meeting Bennys needs! Would 100% use her services again! I felt at ease knowing she was caring for Benny like one of her own

Profile image
Abby G.
Boarding
5.0 out of 5 stars

Dani was wonderful and communicated perfectly throughout my dogs stay with her. I will definitely book with her again!

Profile image
Jimmy A.
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

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

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
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.

Meet local sitters who will treat your dogs like family

  1. 1. Search

    Browse profiles of sitters near you who offer dog boarding
  2. 2. Meet In Person

    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

Popular requests for dog boarding - Windsor

Select a filter and find qualifying sitters offering dog boarding.

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