Dog Boarding in Winsor Hills, Baltimore, MD
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Top rated Winsor Hills dog boarders
“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!”
“My first time leaving my dog with a rover sitter and as expected I was extremely nervous. Shakiyla was so reassuring and professional in handling my big dog! She sent me updates every day while he boarded. I would highly recommend! Thank you!! ❤️❤️❤️”
“Virginia gave the best updates that we've ever had with Rover! Prompt communication, flexible when our plans changed, and really nice about sharing when we forgot Albie's food. Thank you!”
“Davida is so amazing with my dog Akiro. She is extremely accommodating and professional. She knows how to handles my dog and treats him like he is one of her own. anytime I need boarding, Davida is my go to!”
“Jessica was great with my baby. She sent me pics. My baby looked happy from the meet and greet even when he went back 2weeks later like they never missed a bit. Jessica was attentive n lovable. Big thanks Jessica, he will be back. ❤️”
“My puppy had a great stay with Veronica. It was my first time using Rover so I was initially hesitant to leave my puppy with a stranger , but Veronica made it a very easy and pleasant experience. Will request her again!”
“It was a pleasure having Lingli care for my fur baby while I was away. She was always very responsive and sent a lot of pics during my pup's stay. I will definitely be booking again.”
“Brittanie & Ryan were amazing! I had never used this service before and was a bit nervous. They were great and explained how it worked, and I met them before booking to make sure it was a good fit for all of us. It really was!! I could tell they took care of my dog as well as their own. They sent pictures throughout the week and texted back right away with any questions that I had. I can’t thank them enough and would definitely recommend them 100%! What a wonderful family and they loved Lucky and he was so happy with them and their family.”
“Jesse had a blast! Felice and husband are very accommodating and friendly. Thank you for taking care of my baby for the night with such short notice!”
“Robert took great care of our sweet dog, Panda. His cute dog Kirby and Panda got along just fine, and Robert was great about sending us text messages and pictures to keep us up to date on how Panda was doing. Very happy Robert was able to care for Panda while we were out of town!”
“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.”
“Victoria was great! She was very quick to respond and gave us updates on the dogs. Our dogs had a great time staying with her and would certainly recommend her for dog sitting!”
“It was great to leave my Gus with a stranger! Gus has never been away from me and doesn't get much interaction with dogs. Malik communicated with me the first night to say things were going well and them followed up the next night with a photo! I highly recommend Malik and will use him again!”
“Erika was friendly adaptable and kind. Our dog had a very nice stay. Erika sent us a few pictures and sent us periodic updates. We were pleased with her service and hope to use her again.”
“Kyra was fantastic— she boarded my dog Bruno for me for 13 days, and I would 100% recommend her. She sent updates and pictures throughout my trip, and I could tell my dog was happy and healthy when I got back. Her dog Karma was also so sweet and gentle with my dog. Definitely will use Kyra’s services in the future if needed!”
“I had a wonderful experience with Nikki. She took amazing care of my dog while I was out of town. She was attentive, kept me updated and included photos, which gave me peace of mind. When I came back, my dog was happy, healthy and clearly well-loved. I highly recommend Nikki to anyone looking for a caring and trustworthy pet sitter.”
“Carolina is AMAZING!! She is super responsive, sent several photos and updates throughout my puppies stay, and is very patient and diligent about frequent walks and following any specific directions! My puppy is three months old so it is a blessing to have found her as I know puppy care can be a lot of work. I highly recommend Carolina for watching your pets, she eased my anxiety and I know I will be using her 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.”
“Nicole is very nice, easy to work with. Her updates with pictures gave us peace of mind. She always quickly texted back. Our dog seemed like he had a good time. Thanks!”
“Shanikki is an amazing provider. She made both myself and my fur baby feel right at ease. She keep me up to date on how he was doing while under her care. When I picked him up he was relaxed and happy to see me. This was exactly the experience that we were looking for. I will definitely use her services again!”
Over 139 pet parents in Winsor Hills have booked dog boarding
How Rover works
1. Search
Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for dog boarding in Winsor Hills is $40
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 dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Dog Boarding FAQs
Frequently asked questions about Rover
Sitters on Rover are free to set their rates. The median cost to hire a sitter for dog boarding in Winsor Hills on Rover as of Dec 2025 was about $40 per night, after factoring in Rover’s service fees. A sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.
Typically, dog boarding sitters on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your dog in no time!
Experience can vary widely from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when comparing sitters available in Winsor Hills.
Rover makes it easy to find Winsor Hills dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:
- Dogs of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog boarding sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
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