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!

Historic Manor House On Beautiful Eastern Shore Estate - Chestertown, MD
10 35 reviews

Historic Manor House On Beautiful Eastern Shore Estate

apartment, Kingstown
This magnificent 6-bedroom manor house, situated on a 325-acre farm six miles (approximately 9.7km) outside Chestertown, Maryland, on Morgan Creek, offers a tranquil escape near Kingstown.
The 557-square-metre property boasts a private pool, spa, and extensive grounds including walking trails, a vineyard, and shoreline access, alongside concierge services such as a private chef and daily housekeeping.
Historic Chestertown - Chestertown, MD
9.8 168 reviews

Historic Chestertown

apartment, Chestertown
This charming apartment is situated in the heart of Chestertown's historic district, just a short walk from the town's bustling restaurants, shops, and the picturesque Chester River waterfront. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment has three bedrooms and two bathrooms, comfortably accommodating up to five guests. It features a well-equipped kitchen with modern appliances, a spacious living area, and a private outdoor space with a covered porch and a pergola, perfect for relaxing and enjoying the beautiful surroundings.
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.
Walk To Historic Chestertown: Dog-friendly Retreat - Chestertown, MD
No reviews

Walk To Historic Chestertown: Dog-friendly Retreat

cottage, Chestertown
This cottage is located in Chestertown, within 1.5 kilometres of Washington College, River Arts Chestertown, Garfield Center for the Arts, Sumner Hall, and the Chestertown Historic District.
This property offers a well-equipped kitchen with a microwave and dishwasher, air conditioning, and on-site barbecue grills, with WiFi available in public areas.

Frequently asked questions about hotels in Chestertown, MD

  • What are the top landmarks to see in and around Chestertown, MD?

    Well, you have to visit the historic Chestertown waterfront, with its charming shops and restaurants. The beautiful campus of Washington College is a must-see, and the historic houses along High Street are a delight to explore. And don't forget to visit the Chesapeake Bay Maritime Museum, which offers a fascinating glimpse into the region's maritime history.
  • 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 are the most affordable attractions in and around Chestertown, MD?

    For a budget-friendly day out, head to the Chestertown Farmers' Market, which runs from May to October. The market offers fresh, local produce, crafts and live music. Take a walk along the Chester River, enjoying the views and the fresh air. And for a bit of history, visit the Chestertown Historical Society's museum.
  • 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.

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

    Chestertown is a great place to unwind. You can rent a kayak or canoe and explore the Chester River, or simply relax on the waterfront and watch the boats go by. The town has a number of parks, perfect for picnics or a leisurely stroll. And if you're looking for something a little more active, there are several hiking and biking trails in the 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.

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

    Most hotels in Chestertown offer standard amenities like Wi-Fi, cable TV, and air conditioning. Many also have swimming pools, fitness centres and complimentary breakfast. Some hotels even offer rooms with views of the Chester River or the town's historic district.
  • What are the best family friendly hotels in Chestertown, MD?

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

  • 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 the best rates and fewer crowds during these months. However, if you're planning to visit during peak season, be sure to book your hotel well in advance.
  • 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.

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

    The Chestertown waterfront is a great place to take your furry friend for a walk. The town also has a number of dog-friendly restaurants and shops. And for a fun day out, head to the Chesapeake Bay Maritime Museum, which welcomes well-behaved dogs on leashes.

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