Dog Boarding in Chestertown, MD

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. Meghan

Puppy Paradise!

Fort Howard, MD, 21052

Dog Boarding

2 repeat clients

"Meghan did such a great job watching our dog! Our pup was treated like a member of the family and spoiled the entire time she was there. We would definitely ... (more)"

2. Angelene

Oodles Of Poodles Doggy Sleep Over

Edgewood, MD, 21040

Dog Boarding, Doggy Day Care

73 repeat clients

"Angelene is highly recommended. Eran, my golden retriver, stayed with her over the kind Memorial weekend. Angelene updated us day and night about Eran and h... (more)"

3. Irene

Dog lover extraordinaire!

Belcamp, MD, 21017

Dog Boarding, Dog Walking

3 repeat clients

"Irene is just so awesome with dogs! She knew how to handle our pup and she took outstanding care of him, just like one of her own pack. As a doggy sitter she... (more)"

Available this weekend
4. Ashby

I'll love yours like I love mine!

Aberdeen, MD, 21001

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

"We have been so happy with the dog sitting services from Ashby. Not only has she watched our sister and brother Havanese Piper and Tucker, she is also the b... (more)"

5. Rich

Large fenced yard/run space

Joppa, MD, 21085

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

"Rich was great with my dog Marley, he was available last minute and she came home simply exhausted from all the walks and fun she must have had. He was very ... (more)"

6. Cheryl

Animal Lover with Huge Heart .

Belcamp, MD, 21017

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

"Cheryl always takes such good care of my three cats. They absolutely adore her! She gives them extra time and attention. Definitely book her as she is an avi... (more)"

7. Terri

Reliable, mature, petcare provider

Hartly, DE, 19953

Dog Boarding

5 repeat clients

"Terri did a great job keeping our dog Ruby for an extended weekend. She frequently sent pictures and texts letting me know how the dog was doing. I will defi... (more)"

8. Mr. Mike

Mr. Mikes Fitness For Dogs

Edgewood, MD, 21040

Dog Boarding

"They did great with Max and his high maintenance requirements didn't phase Mr. Mike (9 mo old mouthy hound, that howls, drools, jumps, chews on everything an... (more)"

Available this weekend
9. Sydney

The Wag On Inn

Church Hill, MD, 21623

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

1 repeat client

About: I believe dogs, like people, need exercise and play time, and lots of love! I am willing to walk your dogs, or have them stay with me- whether just... (more)

10. Tracy

Home full time love for babies

Baltimore , MD, 21220

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

"Treated my dogs great. Left them for a weekend and came back to a couple of happy, healthy dogs. Definitely would recommend. Tell a friend! (more)"

11. Debi

PAWSITIVELY HERE FOR YOUR FUR KIDS!

MIDDLE RIVER, MD, 21220

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

3 repeat clients

"My dog's stay with Debi couldn't have gone better. First off, Debi has three lovely dogs of her own who are very well taken care of. Her house has great ope... (more)"

12. Jennifer

Home full-time, great neighborhood!

Chestertown, MD, 21620

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

"Jennifer watched our 2 dogs for the day this past weekend. She was great. Very responsive to my emails ahead of time. Very friendly and welcoming to my dogs ... (more)"

13. Ashley

Overnight doggie care

Edgwood, MD, 21040

Dog Boarding, Doggy Day Care

"I forgot in my pervious testimonial to include that Ashley watched our dogs for short hours to upwards of 12 hours; sometimes into the wee hours of the morni... (more)"

14. Mariya

Enjoy my house and fenced back yard

Edgewood, MD, 21040

Dog Boarding, Dog Walking

2 repeat clients

"Mariya was wonderful! She was friendly and accommodating and took great care of Luna! She even spent some extra time snuggling with her, which Luna was very ... (more)"

15. Korey

Koreys doggie daycare

Joppa, Joppa, MD, 21085

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

1 repeat client

"Nellie had a wonderful time with Korey and her little dog Artie. They welcomed her into their home, and she really enjoyed her time with them. Often, Nelli... (more)"

16. Julianne

I'll walk/run/play with your dog!

Chestertown, MD, 21620

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

About: I have had dogs (and other pets) my entire life and I love helping them learn/grow. I grew up with a border collie and a chocolate lab. I current... (more)

Available this weekend
17. Kelly

Personalized attention for your dog

Sudlersville, MD, 21668

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

5 repeat clients

"Kelly was great! She kept us updated with what was Chloe was doing, which was great because we were out of state for vacation. Daisy was also a trooper for h... (more)"

18. Laura

A house is not a home w/o a dog

Aberdeen Proving Ground, MD, 21005

Dog Boarding, Dog Walking

About: I know how much it means to have peace to be able to go out of town and enjoy oneself knowing that the family dog is being taken care of. I would ... (more)

Available this weekend
19. Rhonda

RLJ's Pet Service

Clayton, DE, 19938

Dog Boarding, House Sitting, Doggy Day Care

"Rhonda did a wonderful job with our doggy. She treated her like her own. She communicated with us daily to let us know how Prada was doing. Would definitely ... (more)"

20. Tiffany

Have dogs...Love Dogs!

Edgewood, MD, 21040

Dog Boarding, Drop-In Visits

"Tiffany watched my dog, Tonka, for a week. Tonka had a great time! She was treated like family. We got pictures and updates every day while we were away. Mo... (more)"

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

Learn About Premier

Rover offers the perfect alternative to dog kennels and traditional dog sitting: in home dog boarding. The next time you head out of town and need someone to take care of your dog, turn to Rover for your pet boarding needs. It's easy to find a loving Chestertown 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 in home dog boarding options in Chestertown near you, 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.