Hotels in Chestertown, MD

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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!

Walk To Historic Chestertown: Dog-friendly Retreat - Chestertown, MD
10 7 reviews

Walk To Historic Chestertown: Dog-friendly Retreat

apartment, Chestertown
This Chestertown residence is a 14-minute walk from the Kent County Historical Society and a 15-minute walk to Wilmer Park, offering convenient access to local attractions.
This 90 square metre holiday home accommodates up to six guests, featuring two bedrooms, two bathrooms, a private garden, a terrace, barbecue facilities, and on-site parking.
Pet-friendly Home On Chester River W/ Dock! - Chestertown, MD
No reviews

Pet-friendly Home On Chester River W/ Dock!

house, Kingstown
This four-bedroom house is situated in a peaceful residential area, approximately 77 kilometres from New Castle Airport. The property offers a spacious 300 square metre layout, accommodating up to 27 guests and featuring amenities such as a swimming pool, garden, and private parking.
Loft At Fountain Park - Prime Downtown Location - Chestertown, MD
9.9 86 reviews

Loft At Fountain Park - Prime Downtown Location

apartment, Chestertown
This apartment is situated in the heart of Chestertown, just a short walk from Washington College, the Chester River and the town's historic district, with easy access to shops and restaurants on High Street. The apartment has received excellent ratings for location, cleanliness and overall experience.
This spacious property spans two levels and offers four bedrooms, comfortably accommodating up to eight guests. The apartment boasts a fully equipped kitchen, air conditioning, a garden and parking, ensuring a comfortable and enjoyable stay.
Secluded Cottage  In Middle Of Chestertown - Chestertown, MD
10 2 reviews

Secluded Cottage In Middle Of Chestertown

apartment, Chestertown
This secluded studio apartment offers a romantic getaway in Chestertown, located just 320 metres from the town centre, providing convenient walking access to attractions such as the Historical Society of Kent County Maryland and the Betterton Historic District.
This accommodation features a queen bed, a kitchenette with a microwave and refrigerator, air conditioning, and private parking, with an in-unit washer/dryer and an electric fireplace for comfort, all within a free-standing building set in over an acre of gardens.

Frequently asked questions about hotels in Chestertown, MD

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

    Chestertown is perfect for a relaxing getaway. Spend an afternoon kayaking on the Chester River, enjoy a picnic at the waterfront, or simply relax with a good book on the porch of your hotel. The area is known for its peaceful atmosphere and laid-back vibe.
  • 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?

    Hotels in Chestertown offer a range of amenities, from basic rooms with comfortable beds and private bathrooms to more luxurious options with fireplaces, balconies, and even kitchens. You can usually expect to find free Wi-Fi and cable TV in most hotels.
  • 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.

  • When is the best time to book a hotel in Chestertown, MD?

    The best time to book a hotel in Chestertown is during the shoulder seasons, from April to May and September to October. You'll find better rates and fewer crowds during these months. If you're looking for a more affordable option, consider staying in a bed and breakfast or a vacation rental.
  • 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.

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

    Chestertown is very pet-friendly! You can take your furry friend for a walk along the Chester River, enjoy a picnic at the Chestertown Riverwalk, or visit the dog-friendly shops and restaurants in the historic district. The town even has a dog park where your pet can run free.
  • What are the best family friendly hotels in Chestertown, MD?

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

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

    A short drive from Chestertown, you'll find the charming town of St. Michaels, known for its beautiful waterfront and maritime museum. If you're interested in history, you can also visit the historic town of Easton, which is home to the Talbot County Courthouse and the Academy of the Arts. The Eastern Shore is full of beautiful towns and cities, each with its own unique charm.
  • 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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