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.

“100000000000/10 recommend Veronica!! She treated our little Toaster like her own child! She had a beautiful home that was fully decked out to be a 5 star resort for puppies! She was so knowledgeable about dogs (you would think she was a Vet!) and made us feel so comfortable that our baby would be in the wat of hands!! She even sent us update photos so regularly that we felt like we were there with our baby!! Toaster made so many friends with all the sweet little angels she had and hardly wanted to come home after his stay because he had so much fun!! If you want your baby to stay with someone that will love them and give them as much (and probably even more) attention than you do, then look no further!! Veronica is hands down the best sitter in Baltimore and we cannot thank her enough!!!”

“Nicole was great! Gave us continual updates/pictures & kept my pup active and well taken care of. I would absolutely use Nicole again and recommend her to others!”

“We love sending out dogs to Virginia and Steve. They love on them so much! We use them to watch our dogs every time we are out of time. They truly treat our dogs like their own”

“Our girls just love visiting Liz & the family ! It’s so nice to be able to relax when we are away knowing our girls are also having a blast and getting lots of cuddles.”

“Steven was an incredible host for our retired greyhound! He is incredibly communicative, thorough, and clearly cares deeply for his canine guests. He creates the perfect environment for a dog that prefers some peace mad quiet.”


“This was Rui’s second stay with James and Mary. Mary and James take such great care of our boy when we are out of town. Rui loves them and looks forward to staying with them.”

“Erin was totally a pleasure and kind person to work with. From scheduling a meet and greet with our Maxx a few weeks before to sending updates with pictures. We never once had to worry about my our baby Maxx while chilling on the beaches in Cancun, Mexico.”

“Robin promptly responded to all requests and provided a great experience for our Addie. Clearly comfortable working with dogs, has ample space indoors and outdoors for play. This was our first time and was great experience.”

“Kelly and George were fantastic during Sophie's stay. From the pictures I could tell Sophie was relaxed, loved, and felt at home from the very first day. Will definitely board the pup with them 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.”

“I had a great experience booking with this sitter for my dog Charlie. They took really good care of him, followed all of his instructions, and made sure he received his medication on time. I appreciated the photo updates because it helped me relax and know he was doing well. Charlie came home happy and calm. I would definitely book with them again.”

“Aida sent pictures daily and made sweet observations about our pup, letting me know she sees him for who he is! She showed enormous patience and understanding. Will definitely rebook!”


“Our dog Allie reported that she had an outstanding visit with Diane and family. Came home rested, relaxed, totally chill. Diane was a pleasure to deal with, was responsive, caring, informative. I hope we get back there.”

“Brittanie and Ryan were wonderful sitters for our dog this weekend! She seemed to have gotten very comfortable in their home pretty quickly and had no issue coexisting with their dogs at all. They sent frequent update pictures and really went above and beyond bringing our dog to our wedding so she could be included in our pictures. Overall great first Rover experience and would happily use them again!”

“Thank you Olga for taking care of our Darla while we were away. You always update us of your daily activities with photos & videos. Darla developed that connection already with you. I would definitely bring back Darla to you if need arises. Thank you 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.”

“Amazing! - Our dog stayed for a little over 2 weeks and we consistently received updates and proactive communication. We had to add a few days and it worked with scheduling. Thanks so much, will send her back!!”

The median cost per night for dog boarding in Winsor Hills is $50
Dog parents share their Rover experiences - Winsor Hills
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.

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.

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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