Dog Friendly Chestertown, MD

Chestertown is pet friendly! If you need help to decide where to stay, play, or eat with Fido, you’ve come to the right place. Here’s the scoop on our favorite pet friendly hotels, dog friendly activities, and restaurants that allow dogs in Chestertown.

Places to Stay with Your Dog

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown allows 1 pet up to 80 lbs for no additional fee, and 2 pets up to 80 lbs for $15 per night (not to exceed $105 per stay).… Full pet policy & more

River Lodge

This 4-room lodge in Chestertown is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Full pet policy & more

Brampton Bed and Breakfast Inn

Brampton Bed and Breakfast Inn welcomes dogs of any size in designated rooms for an additional fee of $20 per pet, per night. Only the Apartment and… Full pet policy & more
All 15 Hotels

Places to Eat with Your Dog

Things to Do with Your Dog

Chestertown Farmers Market

Every Saturday, year-round, this market features artisan products from local vendors. Browse the booths of Maryland produce, art, crafts and… Full details & more

Pet Services

Belle Rose Kennels

At BRK we strive to treat every dog as an individual and cater to their needs. We offer boarding, day care, training (agility, obedience/manners,… Full details & more

Traveler Photos

We dug up 8 pictures of dogs in Chestertown.

All 8 Photos

Want to feature your creature? Upload a photo of your pet in Chestertown! You can also share by using the hashtag #bringfido on FacebookTwitter or Instagram.

Add a Photo

Map