Chestertown , MD Pet Friendly Hotels

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Top Chestertown Pet Friendly Hotels

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
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! (772 reviews)
"Great hotel in a great community…. Easily accessible to anything nearby."

Reviewed on Jun 15, 2025

Comfort 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 (171 reviews)
"Mrs Mae is very friendly and helpful. Checks on you to make sure everything is ok. I’d recommend it - stayed 3 weeks for work. Loved my little room!! Mrs Mae was a bonus!!"

Reviewed on May 24, 2025

Driftwood Inn
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.
Great location!
"Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts."

Reviewed on Nov 8, 2024

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

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Comfort Inn & Suites Chestertown, Driftwood Inn, Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

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