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!

Lovely Home In Chestertown With Free Ev Charging - Chestertown, MD
10 99 reviews

Lovely Home In Chestertown With Free Ev Charging

apartment, Kingstown
This apartment is located just a block from the waterfront in Kingstown, within walking distance of shops, galleries, and restaurants, offering a peaceful retreat in a quiet area of Chestertown. It has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
This home, a charmingly renovated "American Four Square" style house, can accommodate up to seven guests and offers full use of the first and second floors. The property features a fully equipped kitchen, comfortable bedrooms with high-quality mattresses, air conditioning, a garden, parking, and internet access.
The Portside Manor - Queen Street Chestertown - Walking Distance To Downtown - Chestertown, MD
10 6 reviews

The Portside Manor - Queen Street Chestertown - Walking Distance To Downtown

apartment, Chestertown
This charming Chestertown home is situated in a quiet residential area, just a short walk from the historic district and the Chester River waterfront. The apartment offers easy access to shops, restaurants, and scenic views. This three-bedroom property comfortably accommodates up to eight guests, with three bathrooms for added convenience. The apartment features a private courtyard, a screened-in porch, two living areas, a well-equipped kitchen, a gas fireplace, off-street parking, and access to streaming services.
Pet-friendly Home On Chester River W/ Dock! - Chestertown, MD
9.4 25 reviews

Pet-friendly Home On Chester River W/ Dock!

apartment, Kingstown
This Chestertown holiday home, located less than 1.6km from Kings Town Park and under 3.2km from the Garfield Centre for the Arts and Wilmer Park, offers convenient access to Kingstown's cultural attractions.
The 300 square metre property boasts a spacious layout with four bedrooms, five bathrooms, and ample room for up to fourteen guests, featuring a private pool, fully equipped kitchen, and outdoor amenities including a terrace and garden.
Quiet, Shabby-chic Home In Downtown Chestertown - Chestertown, MD
9.9 27 reviews

Quiet, Shabby-chic Home In Downtown Chestertown

apartment, Chestertown
This charming house is situated in the heart of Chestertown, just 0.4 kilometres from Washington College and 0.6 kilometres from the waterfront, offering easy access to the town's attractions. The property consistently receives excellent ratings for its location, cleanliness, and overall experience.
The house provides guests with access to the entire property, comfortably accommodating up to four guests. This spacious home features a fully equipped kitchen, a private garden, a fitness centre, and parking, ensuring a comfortable and enjoyable stay.

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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