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Chestertown, MD hotels
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Chestertown, MD Hotels: no available offers. Here are other great options for your stay!

Secluded Cottage  In Middle Of Chestertown - Chestertown, MD
10 2 reviews

Secluded Cottage In Middle Of Chestertown

apartment, Chestertown
This secluded studio flat in Chestertown offers a private getaway on over an acre of gardens, situated just two blocks from downtown attractions and within close proximity to historical landmarks like the Historical Society of Kent County Maryland and the Betterton Historic District.
This rental accommodates two guests and features a kitchenette with a microwave, refrigerator, and coffee maker, a queen bed, a full bath with an in-unit washer/dryer, and a cozy electric fireplace, with private parking available.
Lovely Home In Chestertown -  Free Ev Charging For Guests - Chestertown, MD
10 30 reviews

Lovely Home In Chestertown - Free Ev Charging For Guests

apartment, Kingstown
This Chestertown vacation home offers a family-friendly stay, conveniently located within a 15-minute walk of Kingstown Park, the Historical Society of Kent County Maryland, and the Garfield Center for the Arts, and less than 1.2 miles from River Arts Chestertown and Washington College.
This 1440-square-foot rental boasts three bedrooms, three bathrooms, and accommodates up to six guests, featuring a fully equipped kitchen, free Wi-Fi, a private patio, and is close to several attractions.
Cozy Carriage House - Chestertown, MD
9.7 194 reviews

Cozy Carriage House

house, Chestertown
This newly painted Chestertown carriage house, located behind a Victorian row house, offers a short walk to Chestertown's downtown shops and historical sites.
The upstairs apartment features a modern kitchen, a tiled bathroom, and accommodates two guests with a private garden view, covered parking including EV charging, and easy access to the entire unit and a secure garage.
House On The Hill - Historic Private Second Floor - Chestertown, MD
10 142 reviews

House On The Hill - Historic Private Second Floor

house, Chestertown
This charming bed and breakfast is located in historic Chestertown, just a short walk from the town center and a quick drive from the Chester River. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The second floor is dedicated to guests, offering two bedrooms, a private bathroom, and a sitting area, comfortably accommodating up to four guests. Guests can enjoy the outdoor space with chairs and a fire pit, relax in the sitting area with a mini fridge and Keurig coffee maker, and possibly even meet Andy the orange cat.

Frequently Asked Questions about hotels in Chestertown, MD

  • How can travelers relax during a week in and arond Chestertown, MD?

    Chestertown is a great place to unwind. Spend some time on the waterfront, go for a walk or bike ride on the Chestertown Riverwalk, or rent a kayak and explore the waterways. You can also enjoy a relaxing meal at one of the many restaurants in town.
  • What are the best hotels with a swimming pool in Chestertown, MD?

    Comfort Inn & Suites Chestertown is among the best hotels with a swimming pool in Chestertown, MD.

  • What amenities can travelers expect in hotel rooms in Chestertown, MD?

    Most hotels in Chestertown offer basic amenities like Wi-Fi, cable TV, and air conditioning. Many also have swimming pools and fitness centers. Some hotels might also have a continental breakfast included.
  • What are the most popular 2, 3 and 4-star hotels in Chestertown, MD?

    Among 2, 3 and 4-star hotels in Chestertown, MD, Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown and Holiday Inn Express Hotel & Suites Chestertown are the most popular ones.

  • What are some pet-friendly activities in and around Chestertown, MD?

    The Chestertown Riverwalk is dog-friendly, and you can often see people walking their dogs along the waterfront. You can also take your dog to the nearby Eastern Neck National Wildlife Refuge, which has a designated dog-walking area.
  • What are the best luxury hotels in Chestertown, MD?

    Brampton Bed And Breakfast Inn and Brampton Bed And Breakfast Inn are among the best luxury hotels in Chestertown, MD.

  • Which towns or cities worth a visit near Chestertown, MD?

    If you're looking to explore beyond Chestertown, there are a few great towns within an hour's drive. St. Michaels is a charming waterfront town with a beautiful harbor and a variety of shops and restaurants. Rock Hall is another great option, with a strong maritime history and a beautiful waterfront park.
  • What are the best family friendly hotels in Chestertown, MD?

    The best family friendly hotel in Chestertown, MD is Driftwood Inn.

  • What are the best pet friendly hotels in Chestertown, MD?

    The best pet friendly hotels in Chestertown, MD are Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown and Driftwood Inn.

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