Chestertown , MD Pet Friendly Hotels

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Top Chestertown Pet Friendly Hotels

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Chestertown
This vacation home featured laundry facilities and barbecue grills.
9.8/10 Exceptional! (61 reviews)
"The house and hospitality exceeded all expectations! We had a wonderful long weekend away and would definitely return. The kids especially loved fishing, kayaking, and the paddle boat. The farmer’s market was enjoyable Saturday morning, too. We had beautiful weather for yard games and the fire pit. ..."

Reviewed on Sep 1, 2025

Opens in a new windowChester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

150 Scheeler Road, Chestertown, MD
$102 nightly
The price is $113 total per night from Oct 20 to Oct 21
$113 total
Oct 20 - Oct 21
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will ...
8.4/10 Very Good! (825 reviews)
"Nice hotel"

Reviewed on Sep 29, 2025

Opens in a new windowComfort Inn & Suites Chestertown
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD
Free self parking is available and the motel's front desk is staffed around-the-clock. WiFi in public areas is free. Express check-in and express check-out are ...
5/10 (174 reviews)
"Rooms are clean, staf was helpful"

Reviewed on Aug 18, 2025

Opens in a new windowDriftwood Inn
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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


  1. Great Oak Manor
    Pets are allowed for a fee at this 3.5-star bed & breakfast, although restrictions apply. Guests appreciate the breakfast.
  2. 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
1,079 hotels
Lowest Price
$113
Highest Price
$113
Popular hotels
Comfort Inn & Suites Chestertown, Driftwood Inn, Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Recent Chestertown hotel reviews by fellow wanderers

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