Dog Boarding in Winsor Hills, Baltimore

Find a loving dog sitter to watch your dog overnight at your sitter's home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Lindsay

Jon & Lindsay's Dog Country

Gwynn Oak, Gwynn Oak, MD, 21207

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

18 repeat clients

"Lindsay was wonderful with Bella and is very knowledgeable about introducing dogs to each other and caring for dogs in general. Bella was comfortable with he... (more)"

2. Dalton

Your pets get undivided attention

Reservoir Hill-Bolton Hill Area, Baltimore, MD, 21201

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

3 repeat clients

"Shiloh loved his stay with Dalton! We received daily updates of activities and behavior. We will definitely have Dalton watch Shiloh next time we go out of t... (more)"

3. Ravenn

Home full-time, plenty of walks.

Roland Parl-Homewood-Guilford, Baltimore, MD, 21210

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Ravenn made sure my two puppies received the care and attention they needed, and my house was very well kept! She even fed my cat and hamster for me. In fact... (more)"

Available this weekend
4. Jenn

I love dogs and work from home

Catonsville, MD, 21228

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

"My little Kenna is a very shy 15 y.o. Bichon. I was very grateful for how well Jenn cared for her and texted detailed updates each day including pictures. ... (more)"

5. Tyler

Student home full-time love dogs

Govans, Baltimore, MD, 21218

Dog Boarding, Doggy Day Care, Dog Walking

2 repeat clients

"Tyler was great! She was super responsive and sent plenty of pictures of Archie while I was traveling. He was exhausted when I finally picked him up and I kn... (more)"

6. Anna

Experienced and Loving Pet Pal

Reservoir Hill-Bolton Hill Area, Baltimore, MD, 21202

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

7 repeat clients

"Anna took excellent care of Gunner while we went away to NYC for the weekend. She sent pics of their walks and was always responded quickly. (more)"

7. Lauren

Dog Lover, Home Full-Time!

Reservoir Hill-Bolton Hill Area, Baltimore, MD, 21202

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

14 repeat clients

"Sent several pictures and Huey had a great time! He was in a great state when picked up and I could tell from his walk after that he was fed properly ! He ga... (more)"

8. Genevieve

I love all dogs, big or small!

Reservoir Hill-Bolton Hill Area, Baltimore, MD, 21217

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"With 2 dogs, it is not easy to get out, and when they are your kids it's hard to trust someone to take care of them. Genevieve has always treated our dogs li... (more)"

Available this weekend
9. Keith

Dog-loving AT-HOME Dad w/ YARD

Hampden-Woodberry-Remington, Baltimore, MD, 21211

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

38 repeat clients

"Keith and his family were a perfect fit for our dogs! Having recently relocated to the area we were a little nervous about finding a sitter for an overn... (more)"

10. Shannon

Animal Lover

Hampden-Woodberry-Remington, Baltimore, MD, 21211

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

31 repeat clients

"Shannon was great! Super responsive and easy to communicate with throughout. Our dog is crazy and Shannon seems to like her, so everyone is happy :) (more)"

11. Raven

Active,loving family for fur babies

Greater Mount Washington, Baltimore, MD, 21209

Dog Boarding, Drop-In Visits, Dog Walking

2 repeat clients

"Highly, highly recommend Raven! She and her family were so good to my Bear! They took him in during the Thanksgiving holiday and sent photos nearly everyday.... (more)"

Confirmed New Years Availability
12. Brigid

A LOVING HOME WELCOMES YOUR PET

Roland Parl-Homewood-Guilford, Baltimore, MD, 21210

Dog Boarding, Dog Walking

12 repeat clients

"This was Carly's first stay with Brigid and she had a great time. Brigid took great care of her and sent us frequent photo updates. Carly looked happy and co... (more)"

Confirmed New Years Availability
13. MindiMeira

Health Coach & Mom to 7 Sons

Cheswolde Area, Baltimore, MD, 21215

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Mindi was amazing! I really appreciate that she and her family took my dog for a day realizing that he is a totally lovable but a handful indeed:) My unexp... (more)"

14. Joanne

Temporary loving home for your dog

Greater Mount Washington, Baltimore, MD, 21209

Dog Boarding, House Sitting

10 repeat clients

"Joanne did such a fantastic job with our dog. She followed all of our instructions and sent us several pictures and updates thru her stay. We will surely use... (more)"

Available this weekend
15. Molly

Furchildren welcome! :)

Reservoir Hill-Bolton Hill Area, Baltimore, MD, 21217

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"As usual, Eleanor had a fantastic time with Molly and Molly's dog Lucca - I know that I don't have to worry when I go away, as Eleanor is in safe hands at Mo... (more)"

16. Rob

Dog lover: overnights and walks!

Roland Parl-Homewood-Guilford, Baltimore, MD, 21211

Dog Boarding, Dog Walking

1 repeat client

"Rob was a great communicator, sent us wonderful updates about our Lu while we were out of town. He was flexible on drop off/pick up arrangements, and very ac... (more)"

Confirmed Holiday Availability
17. Snezhana

Dogs make us happy!

West Baltimore, Baltimore , MD, 21223

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

7 repeat clients

"Snezhana did a great job! She was really kind and friendly. You can tell that she genuinely enjoys dogs. Hans has his little quirks, but she was good about f... (more)"

18. Jessica

Head over heels in puppy love!

Grove Park, Baltimore, MD, 21207

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

5 repeat clients

"It was super easy working with Jessica. She was flexible, and very responsive. Raven seemed very comfortable, and happy. I would have Jessica care for my dog... (more)"

19. shannon

Home fulltime to care for your pup!

Madison Park, Baltimore, MD, 21217

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

44 repeat clients

"Shannon took great care of my pup and sent me picture updates! She definitely helped me feel less anxious about being away from my dog for a couple of days. ... (more)"

20. Steven

Fenced yard with a playmate.

Park Heights, Baltimore, MD, 21215

Dog Boarding

1 repeat client

"Steve and family..you are the best. All the communications and love shown to my baby. He had soooo much fun with Ollie. I was blessed to find you. You’re our... (more)"

Dog owners in Winsor Hills, Baltimore, MD love booking dog boarding with sitters on Rover.com. Over 2,462 pet owners have reviewed dog sitters in Baltimore, giving them an average rating of 5.0/5 stars. Booking dog boarding can be super affordable, no matter where you live. Trust us, we think you'll be pleasantly surprised. Curious what it might cost to book dog boarding with Rover? Check out our average dog boarding rates to get an idea before reaching out and starting a conversation with a dog sitter near you in Winsor Hills.

Rover.com offers the perfect alternative to dog kennels and traditional dog sitting. The next time you head out of town and need someone to take care of your dog, turn to Rover for your dog boarding needs. It's easy to find a loving Winsor Hills dog sitter on Rover who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at their sitter's home. Search from hundreds of dog sitters in Winsor Hills, Baltimore, MD, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. With Rover, pet boarding is guilt-free, cashless, and convenient. That way, you can hit the road happy knowing your dog's in loving hands while you're away.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a pet sitter or dog walker. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

Book a Stay, Donate to a Cause

Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover sitters in Winsor Hills, Baltimore donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Baltimore.

We're proud to support over 200 organizations across the nation, including: