Chestertown , MD Pet Friendly Hotels
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Top Chestertown Pet Friendly Hotels
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
"Great location and private setting on the river"
Reviewed on May 28, 2026
Great Oak Manor
"Plenty of privacy"
Reviewed on Feb 15, 2022
Comfort Inn & Suites Chestertown
"Clean and comfortable. My only complaint is I'm an early riser and coffee wasn't available till 7:00 but there is a dunkin' donuts across the street. I would stay again."
Reviewed on Jul 26, 2026
Driftwood Inn
Pet lovers shouldn't miss the chance to visit Chestertown, a family-friendly and quaint city known for its boating, as well as great sights like Wilmer Park and Garfield Center for the Arts at the Prince Theater. You can choose from Travelocity's 4 pet-friendly hotels and accommodations in Chestertown and bring your pooch along!
How to Wander Wisely in Chestertown with Your Pet
- Culture enthusiasts will want to visit Historical Society of Kent County Maryland.
- Other things to see include Rolphs Wharf Marina, Cassinelli Winery and Vineyards, and The Mainstay.
- Need a pet store? Try Green Fish Aquatics Aquarium Service.
- For vet care, Chestertown Animal Hospital, Eastern Shore Animal Hospital, and Hash Gary R DVM are located in the area.
Featured Pet-Friendly Hotels in Chestertown
- Great Oak Manor
Pets are allowed for a fee at this 3.5-star bed & breakfast, although restrictions apply. Guests appreciate the breakfast. - Holiday Inn Express Hotel & Suites Chestertown
Pets are allowed for a fee at this 2.5-star hotel. Guests appreciate its great beach location and comfy beds.
Pet-Friendly Times to Vacation in Chestertown
Weather can make or break your trip, especially if you want to spend time outdoors. We have gathered the average daytime and nighttime temperatures to help plan your time in Chestertown.
From January to March, average temperatures range from 58°F in the daytime to 25°F at night. Between April and June, the daytime average is 85°F and the nighttime average is 39°F.
From July to September, average temperatures range from 87°F in the daytime to 53°F at night. Between October and December, the daytime average is 73°F and the nighttime average is 28°F.
Chestertown hotels essential information
Accommodation | 1,083 hotels |
|---|---|
Lowest Price | $70 |
Highest Price | $115 |
Popular hotels | Comfort Inn & Suites Chestertown, Driftwood Inn, Great Oak Manor, Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town |
Recent Chestertown hotel reviews by fellow wanderers
Pendry Baltimore
"A gorgeous property in the best location with the nicest staff."
