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

Over 105 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.

“This was my second time using this family, but this time I also brought my 7 month old rescue puppy who has way too much energy and is a handful. They handled both my older dog and the puppy extremely well. Neither dog was stressed when they got home. I highly recommend this family for taking care of your dogs.”

“Alex took great care of my Mini Aussie Tango these last several days, including timely communication and updates! His place with the large enclosed grass yard was perfect for Tango to get her energy out. She really enjoyed her time with Alex’s dog Reese and came home happy and exhausted!”

“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.”

“Nikki seemed very knowledgeable sweetheart how to take care of our dog's anxiousness and energy from the get go. It helped a lot that she had a fully fenced yard and no pets of her own when we booked her. From meet and greet to pick up, she made it easy for everyone. We specially appreciated her updates and our dog truly enjoyed staying at her place. We also appreciated the tips and other feedback she gave us, as we are first time pet owners and our dog has some unique needs. Definitely will use her services again.”

“Aida was a wonderful sitter and my dog had a great time with her! He enjoyed time spent in her large yard, many walks, and an overall comfortable stay. She shared frequent updates and pictures, and was happy to adapt to my dog’s routine and quirks. I felt so comfortable and was able to enjoy my trip, knowing my dog was in fabulous care.”

“Ginnie took excellent care of Koda during his 5 night stay! She sent a lot of great updates and pictures during our trip to let us know how he was doing. It seemed he had a blast playing with all the other dogs! He felt right at home and it was nice knowing we didn’t need to worry about anything while on vacation. Highly recommend letting Ginnie look after your pet and we will definitely be using her services again!”

“Shruti is very caring and considerate of my dog who has separation anxiety. She worked with me to find the best solution for her. I've already booked her this time for an extended stay while I am travelling.”

“OMG, Awesome!! Nicole and her family were the perfect overnight host for Rex!! They were engaging and attentive with Rex. He ate up the attention!! I booked 2 more future bookings because Rex and I received good vibes from them, 100 thumbs up 👍 for Nicole and her family !!”

“Robin and her daughter, are truly tuned in to the dogs that they care for. They reassured not only my little dog, Piper, but also me! —and calmed my nervousness about leaving Piper for the first time. Besides showing Piper and me the whole layout of their dedicated pet spaces, they carefully checked my notes and expectations regarding Piper’s care and medication, and clearly followed all guidelines. Best of all, they regularly sent pictures and videos which reassured me completely that Piper was having a wonderful time while I was away! I will be completely comfortable and happy to bring Piper back to Robin whenever I need excellent pet care again!”

“Cheryl was amazing! We constantly received pictures and videos of our fur baby and never had to wonder how he was doing. She was also very accommodating of us when we were late to pickup due to our flight being late. Highly recommend!”

“Dozer had alot. Of fun boarding with Shakiyla! He got a lot of time to play and tons of walks over the weekend. Will book with her again next vacation!”

“I have been blessed to find someone to care for my baby like I do. Davida is the best sitter ever and you will never want to use anyone else once you have her sit for your baby. She goes above and beyond.”

“Kellyn took great care of our dog! We appreciated the periodic updates. I can tell that she went above and beyond in making sure Mariner was safe and comfortable. We look forward to booking again!”

“Thank you soooo much Lia! She really came in clutch with the last minute booking in the middle of a snow storm! Long story short I work at the ER and was expected to stay over at least for 5days to cover outa due to the snow. She accepted “Kash” the day of and treated him so well. How do I know this you ask? Because for one I’ve had other people watch my dog before and he came back to me timid and afraid. So I knew something wasn’t right. But Lia she kept me involved every step of the way and answered whenever I contacted her in record time. If she will have us we will definitely be returning 💕 She’s a true animal lover and it shows😇”

“Shannon did an amazing job watching our two pups for a week while we were on our honeymoon. She kept us informed, sent of lots of photos of the pups, and (most importantly) took great care of them. Thank you, Shannon!”

“I am most appreciative of the kind care that Alexis gave to my pup. And am even more grateful for the pictures and messages that he sent to me to put my mind at ease. Knowing that she was doing well helped me to enjoy my time away.”

“Sarah was so kind. I really felt great about Yani’s care with periodic pics and updates from Sarah. She showed really good care for Yani and I would certainly recommend!”

The median cost per night for dog boarding in Winsor Hills is $50
Dog parents share their Rover experiences - Winsor Hills
As always, Ashley is incredible with our girls and they always seem very relaxed and not stressed when we pick them up, their medical needs are always met, we get updates and never feel stressed about them being well taken care of. 5/5 every time! Thank you for watching and loving our gals so well

Ms. Jae is absolutely wonderful. She took my baby girl in as her own this past weekend and even had another energetic pup visiting that Cora could enjoy spending time with. Ms. Jae knew that I was worried given a few of my past experiences here in Baltimore and she made it her duty to send me multiple updates and photos throughout my time away from Cora. My was smiling the whole time, and I could really tell that she was happy and well cared for. You can tell that she really cares about making your pet feel safe, comfortable, and loved in her space. If I could give 10 stars I would. I will likely only send her to Ms. Jae from now on as long as she will have her ❤️❤️❤️❤️❤️❤️❤️

I can’t say enough nice things about Sean and the wonderful way he took care of our fur baby, Taz. He kept me up to date with Taz’s daily activities and added pictures. I am so grateful for Sean and his excellent care of Taz. I will definitely use Sean again in the future!

Cheryl was awesome! She welcomed my fur baby into her home and treated him like her own. She provided updates, pictures, and videos. And as a bonus my fur baby got to hang out with her beautiful daughter. I could not ask for a more "genuinely" compassionate, and loving family to leave my boy with. I would completely use her again. Thank you so much Cheryl!!!

Olivia is friendly, positive, accommodating, loving, communicative and very responsible -- in short, everything you could want in a sitter for your four legged fur baby! We drive 30 minutes **each way** specifically so we she can care for our beloved pup when we have to go out of town. She checks in often and sends plenty of pictures so we know our pup is getting the best care (and behaving!) Her home is lovely -- spacious, welcoming and just right for a pup who might sometimes be a little too curious for her own good. We highly recommend Olivia! You cannot go wrong with her.

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.

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?
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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
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
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