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

Over 161 pet parents in Winsor Hills have booked dog boarding
Winsor 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.
“Steven was very attentive to the needs of my Aussie. He was very thorough in the meet and greet, and was knowledgeable about canine care and behavior. I was very comfortable leaving Whiskey in his care (I’m a very picky dog Mom!) and I picked up a happy, healthy dog after his stay. I would have no concerns leaving your pet in the hands of Steven. Thanks for a great stay!”

“Our 8 month old Husky, Penny, just spent 12 days at Ginny's while our family took a trip to Thailand. Ginny made us feel at ease that Penny was well taken care of through her regular communication. On a daily basis we received an account of Penny's fun filled day, along with pictures of her. We will definitely request to board Penny at Ginny's if we need a sitter. It is comforting knowing your animal family member is having a good time too, on their own vacation. One can tell that Ginny and her husband genuinely love animals. We were very pleased.”


“Bo and I feel so fortunate to have found Felice! We used her for the first time this past weekend. I was nervous because Bo has the worse separation anxiety and would literally stop eating while he is away from me. But as soon as we met Felice I could tell he liked her and her home. Well, Felice took such great care of him that he finished the food I sent with him! (Which is a first!!!) Felice kept me updated with lots of pictures of him and he looked very comfortable and HAPPY! He came home vibrant and content! I could tell he really enjoyed his stay in her home! I already told Felice I plan to use her again.”

“Virginia was amazing. Our dog loved being at her house with her two dogs and was thoroughly worn out after playing at her house all day. Will definitely be using Virginia again.”

“Our pup’s overnight with Shannon was absolutely wonderful! Shannon is very nice and it is evident she really loves and cares for animals. She took great care of our Boston Terrier she kept us posted regularly on how he was doing with photos of him playing with the other dogs. It’s a big relief to know we can bring him there the next time we are going to be away and know not only that he will be in good hands but that he’s happy and having lots of fun.”

“Liz and Jeffrey took very good care of our dog while we were gone for 10 days. We received daily updates with pictures and our dog loved to play and hang out with their dogs. We will for sure be back for future dog sitting and maybe also some day care. Thanks a lot Liz and Jeffrey for taking good care of Mayla!”

“Erin did a wonderful job taking care of Ruby, keeping me updated with messages and photos. Ruby loved her time with Erin and her adorable pup Bailey and I am sure looks forward to future "sleepovers."”
“Fallon was great! I appreciated that she sent updates and lots of pictures. I could tell that Paddington had a great weekend. Fallon has a true love for dogs, and animals in general. I would for sure recommend her to watch your pet!”


“Jill was great, very communicative and sent us daily pictures of our pup while he was boarding with her. Our pup seemed to have lots of playmates and was well cared for!”


“Maurie received lots of TLC, plus Veronica kept me up to date with photos and texts. My pup came home very calm and relaxed after his stay. I will definitely book with her again.”

“Junie comes back happy and healthy! We received lots of great pictures of her walks and hangout time with dog friends. Julia is quick to respond to messages and knows a lot about dog behavior.”

“Olga is absolutely marvelous very patient and so kind We are so lucky to have found her for Romeo She is a great nanny we recommend her very warmly Romeo had a wonderful Thanksgiving thanks to her - and we too! He is thrilled to meet Olga again Thanks you Olga for your seriousness and kindness”

“Casey and Marwa are the most accommodating and caring dog sitters, we have ever had. They do their best to keep with the routines that Indiana knows and then add extra long walks, treats, brushing, playing, and lots of love. Their Pug Kevin is so cute and friendly. On top of that, they are super-flexible with drop off and pick up times and took Indy in on very short notice. Will definitely be back”

“Melissa is very attentive and accommodating. I can tell Zelda is very comfortable with Melissa and her pups. She immediately starts playing and doesn't seem anxious at all. Thanks, Melissa!”

“Robin went above and beyond to make sure my pup felt at home and loved! This was my first time leaving my fur baby with someone other than family. Needless to say, I was an emotional wreck. As we were leaving, we thought our dog would start crying and scratching at the door, but no, she followed Robin inside immediately. Robin took many videos and pictures throughout my dogs stay and sent them to me knowing I was a bit nervous. This calmed my nerves and I was able to enjoy my vacation. I’m going to definitely leave my baby with Robin when I go again!!!”

“Brittanie, Ryan and their family were absolutely amazing sitters for our Milo! He loved getting to play with their dogs and kids. They sent pictures throughout his stay and updates on him. We were really reassured. We can tell Milo would love to come back!”

“My pup Izzie LOVES herself some Ashley! Ashley has taken great care of Izzie during several of my work trips and most recently when I had to go out of town unexpectedly for a memorial service. I truly appreciate the photos and videos Ashley sends while taking care of my girl -- it really puts my mind at ease to see how happy my pup is while staying with Ashley. She is the best!”

“Nicole and her family are awesome!!!!! Wish I could give more than 5 stars. Very loving and attentive, especially with us having a very high energy husky. Will highly recommend to anyone and everyone”

The median cost per night for dog boarding in Winsor Hills is $50
Dog parents share their Rover experiences - Winsor Hills
Great petsitter!!! My dogs were so happy being there and coming back home. Nautica kept my daughter and I updated daily with videos and pics of their journeys. One of dogs has anxiety problems and she made sure he was comfortable. Nautica followed our feeding directions and walking schedules. My dogs did not have any accidents while in her care.
I really appreciate Shakiyla. I contacted her in short notice due to my daughter being in the ER and not being able to find anyone to watch Reign. She responded immediately and was great with my dog. I was very nervous using this app for the first time, but She sent videos and kept me posted about how Reign was doing. She was a life saver. Thank you so much.

Nina was such a blessing to find as I was looking for last minute care for my pup! She welcomed Sweet Pea into her home and within the evening she was settled and I could tell she felt at home. She shared pictures throughout the stay and was super communicative which I appreciated greatly! She came home tired and so happy - couldn’t ask for more!

I’m so grateful that I found Kassandra to board my dog, Benji! The consistent updates and photos provided throughout, gave me such peace of mind while I was away. Kassandra and her adorable son will love your dog like their own to make the absence easier on your pup. Oh, and benji got spoiled with that amazing fenced in yard! 10/10 recommend.

Sean was great a fit for boarding my two girls Xena & Rogue! I went away for 10 days, they both got multiple daily trail walks, a quiet neighborhood, and a great living space on his ground floor. Sean would give a daily update most days with 1-2 photos so I could see they both looked well. I returned to two happy, healthy pups that seemed content being in Sean's home. Thank you Sean!

We are so happy that we found Helen to take care of our "four legged baby". Our dog was taken care like a king, knowing that Helen did such a wonderful job with our dog gave us piece of mind, we were able to relax during the time away from our dog. Helen send us great pictures of our dog. Helen is just fantastic!

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- 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?
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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
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