Dog Boarding Windsor Hills
Find a loving dog sitter to watch your dog overnight at your sitter's home.

Over 12,245 pet parents in Windsor Hills have booked dog boarding
Windsor Hills, 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.
“I’ve been using Rover for a couple of years now and I’ve run into some awesome sitters. That being said, I haven’t met any pet sitter on or off of Rover that compares to Cheyanne!!! Literally a pup sitter sent straight from the heavens above guys. She not only sent us multiple pictures and updates of Kai every single day but with every single photo I could see how happy Kai was and even how much love, attention and one on one playtime she had been giving her! I’ve never been as content, comfortable and worry free with a sitter on the first sitting. I mean she even let her snuggle with her for bedtime? If my pup could talk I’m sure she’d say that it doesn’t get any better than Cheyanne!! Cheyanne, thank you thank you thank for giving our sweet girl such a phenomenal home while we were away. If you’re reading this and looking for a sitter, just go ahead and book her NOW! (Literally now, she books up super super quick! We thankfully got lucky and were able to book due to a cancellation.) So lucky to have found you, Kai will most definitely be back :)”
“Jacob was great as always. He has watched our two babies many times now. So grateful to have a reliable and trustworthy person we can rely on. We travel so carefree knowing our doggies are in good hands.”

“Janie was great with my mini schnauzer, Pete, as always! Very communicative and took extra special care over the 4th of July holiday with lots of fireworks and anxiety.”

“Valeriia was the sweetest and most patient with my dog that has a hard time with new people. She was so attentive towards him and always respecting his pace towards meeting new people. She was very responsive and always keeping me updated on my dog’s day while I was out of town.”

“Sarah was great to our pup! She shared sweet photos and updates throughout the visit. I learned from Sarah about a different style of leash that is much more comfortable for our pup!”


“Lisa took exceptional care of our kitty while we were away for extended time. She made sure to take plenty of pictures and even a video of our kitties playing together! She is quick to respond and very communicative. Willow even received a parting toy when we came to pick her up! Thank you Lisa!”

“Eddie & his wife were absolutely AMAZING! They sent tons of photos & updates, took Brewski for a walk & I know he was well taken care of as if he were their own! My dog had such a blast with Eddie’s family (including their dogs)! HIGHLY recommend & will definitely use again in the future!”

“You can tell he genuinely cares about dogs. My dog is not an easy dog, he's a very anxious boy and uncomfortable around strangers. From what was able to tell, my dog looked comfortable and happy in his care. Onel and his wife are so nice and pet lovers. They will update me from time to time with pictures. I highly recommend Onel :)”

“Our pets absolutely loved staying with Israel! They were well taken care of, and we got many great pictures and videos during their visit. We will definitely be booking here in the future.”

“Stephanie was so good with our dog Lucky. It was her first time without us for a week and Stephanie worked so hard at gaining Lucky’s trust and sent us updates to help us feel at ease. We were able to fully relax and enjoy vacation knowing that Lucky was in good hands. Thank you Stephanie ❤️”

“Jen came highly recommended and I am so happy to have had her watch over Peanut and Chloe. This was our first boarding experience and she handled these newbs like a pro. The frequent photo/video “pupdates” are the best. She knows how to handle nervous small dogs and glad my pups had an opportunity to socialize with her small ones. Thank you!”

“Daniel was very friendly, communicative, and put in extra effort to make sure I was not only comfortable, but confident leaving Oliver with someone I had never met.”

“Amber is fantastic. For Buddy's stays its like a vacation for him. Amber is so good to him. And as Mr Social, little Buddy loves spending his time in the company and large yard with other dogs. Thank you so much. Phillip & Sally”


“Melissa provided frequent updates (with cute pics of my cat!!), responded very quickly, and made me feel comfortable leaving my kitty with her. 10/10”

“Nhu & Kevin were great. I was EXTREMELY nervous dropping off my pet for a full week as he normally stays with my parents while we're away and he had just undergone dental extraction surgery a few days prior which meant he had an unusual routine of meds and diet. After the first few days of our trip, I felt extremely anxious being away from our boy and Kevin reassured me, calmed me down, and sent extra pictures and videos for the remainder of our trip. To make matters more complicated, we faced major travel delays returning to the country. Despite the uncertainty and an 8 hour time difference, Kevin stayed responsive and allowed us to confirm our return date just minutes before takeoff. Throughout it all, he reassured us that Beamer would be taken care of. I absolutely loved seeing the bond Nhu developed with Beamer over photos, I think he may have won her heart over! Not only did they do great with our dog, they did great with us as first time Rover users and we are extremely grateful. We can't wait to use Nhu and Kevin again in March!”

“Angela and the other adults in the house are very kind. They sent photos of my pups during their visit, and I could tell they were very relaxed. They have a beautiful backyard which my older dog loved lounging in. Will book again!”

“Alice was able to accommodate my urgent request after another sitter canceled on me last minute. She was very flexible and communicative providing regular updates along with pictures. She did an amazing job caring for Macaroni and I will be using her for any future requests. I highly recommend Alice to care for your pet!”

“Benita was excellent overall. She communicated very well via text and kept me updated at all times. She sent many pictures, was attentive and followed the instructions for my baby (medicine, walk schedule, etc.) and made sure my dog was well settled and comfortable.”

“David was great! Communication was clear throughout the entire process. He sent multiple pictures and videos of Junie during her visit. Even gave me a little picture of her in a frame! I will continue to come back in the future!”

The median cost per night for dog boarding in Windsor Hills is $47
Dog parents share their Rover experiences - Windsor Hills
Wonderful experience working with Casandra. She responded promptly as we coordinated care for my doggie, sent me daily photos during the stay, and was kind and considerate throughout the process. I will definitely be asking her to take care of my pup the next time I go out of town.

Casey is awesome! Our dog has stayed with her overnight a few times, and she kept us updated with photos throughout the stays. She was very responsive and easy to communicate with, which gave us peace of mind. We’d definitely recommend her and would happily book with her again!

Shreya was amazing. She was very communicative and send lots of pictures of Charlie enjoying many walks and lots of attention and pets from her. She was also very easy to meet up with and I really appreciate her accommodating our last minute request. Would definitely recommend.

Mi was amaaaazinggg! She sent lots of pictures of my babies. My older doggo has a lot of medication and food needs (prescriptions from vet) and Mi was able to give everything on time as needed. She gave my kitties a lot of play time as well! My fur babies adore her and got so excited when she came over again after the meet and greet

Jin and her family were amazing with Teddy. She sent me lots of pictures of him everyday and her kids seemed to love Teddy. She kept me updated on his eating, sleeping, walks and playtime. Overall, I would give Jin at 5stars and we will most certainly be using her and her family in the future.

Natalie is such a sweet woman and I am so happy to have chosen her to watch my dog, Finnegan! Natalie communicated throughout the entire time Finney was with her, sending pictures and raving about how much she loved him. Plenty of walks and cuddles — even through his anxiousness during some storms. I am certainly going to be using her more and would recommend her to anyone asking for a sitter on Rover! Never once was I worried with his care while he was there and it made vacation even more enjoyable knowing he was loved, cared for and treated like her own!

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 to book dog boarding

1. Search
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2. Meet In Person
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3. Book & Pay
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