Bed and Breakfast in Chestertown, MD

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7 nights
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Chestertown, MD bed and breakfast
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Chestertown, MD Bed and breakfast: no available offers. Here are other great options for your stay!

Classic Victorian In Chestertown - Chestertown, MD
9.9 163 reviews

Classic Victorian In Chestertown

apartment, Chestertown
This charming Victorian house is situated in Chestertown, just a short walk from the historic district and waterfront, providing easy access to the town's attractions. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
This spacious home offers four bedrooms and two and a half bathrooms, making it ideal for families or groups. Guests can enjoy a gourmet kitchen, a private garden, and a garage with electric vehicle charging, perfect for exploring the area.
Waterfront! Private Dock, Boat Tie-up & Near Town - Chestertown, MD
10 4 reviews

Waterfront! Private Dock, Boat Tie-up & Near Town

apartment, Rock Hall
This spacious waterfront property in rural Rock Hall, Maryland, is an eight-minute drive from Rock Hall Harbour and ten minutes from Ferry Park.
The 136-square-metre (1463 sq ft) boat boasts five bedrooms, three bathrooms, sleeps twelve guests, and includes a fully equipped kitchen, terrace, garden, Wi-Fi, and pet-friendly facilities.
Bright, New Apartment In The Heart Of Chestertown - Chestertown, MD
10 143 reviews

Bright, New Apartment In The Heart Of Chestertown

apartment, Chestertown
This Chestertown apartment is located on the second floor of a historic building on the main street, just a short walk from shops, restaurants, and the waterfront. It has received excellent ratings for location, cleanliness, and overall experience.
The apartment is spacious and can accommodate up to four guests. It is equipped with a fully fitted kitchen, a washing machine and dryer, and a Smart TV, as well as high-speed Wi-Fi and off-street parking for one car.
The Lodge At Great Oak Landing - Chestertown, MD
8.0 99 reviews

The Lodge At Great Oak Landing

chalet, Fairlee
This chalet is located in Chestertown, Maryland, just 14km from Washington College and within 26km of both the Garfield Center for the Arts at the Prince Theater and The Mainstay. The chalet has received very good ratings from previous guests.
The accommodation has a private sand beach, a golf course and a volleyball court. This chalet also provides a restaurant, a bar, a fitness center and housekeeping services on request.

Frequently asked questions about bed and breakfast in Chestertown, MD

  • What are the must-see sights for first-time visitors on a day trip to Chestertown, MD region?

    For a day trip, you'll want to visit the historic Chestertown waterfront, with its charming shops and restaurants. The beautiful campus of Washington College is definitely worth a stroll, and the Chesapeake Bay Maritime Museum is a great place to learn about the region's nautical heritage.
  • What are the best bed and breakfasts in Chestertown, MD?

    Among the B&Bs in Chestertown, MD, Piney Grove Farm, Private Room W/bath: Walk To Washington College and Brampton 1860 are the most popular ones.

  • What weather can travelers expect when exploring nature in Chestertown, MD?

    Chestertown has a humid subtropical climate, so you can expect warm, humid summers and mild, wet winters. Spring and autumn are lovely times to be outdoors, with temperatures ranging from 10 to 25 degrees Celsius. You'll want to pack layers, as the weather can change quickly.
  • What are the best bed and breakfasts with a pool in Chestertown, MD?

    The best B&B with a pool in Chestertown, MD is Piney Grove Farm.

  • What outdoor activities can visitors enjoy in and around Chestertown, MD?

    Chestertown is a great place to get outdoors! You can enjoy kayaking or canoeing on the Chester River, explore the scenic trails at the Chestertown Riverwalk, or visit the nearby Elk Neck State Forest for hiking and camping.
  • What are the best bed and breakfasts for families and kids in Chestertown, MD?

    The best B&B for families and kids in Chestertown, MD is Private Room W/bath: Walk To Washington College.

  • What famous cities can be easily accessed from Chestertown, MD?

    Chestertown is about a 1.5-hour drive from Baltimore and a 2-hour drive from Philadelphia, making it easy to combine a visit with exploring those cities.
  • What are the best pet friendly bed and breakfasts in Chestertown, MD?

    The best pet friendly B&B in Chestertown, MD is Piney Grove Farm.

  • What local breakfast specialties can you enjoy in Chestertown, MD region?

    For a true taste of Chestertown, start your day with a local favourite: a Chesapeake Bay crab cake Benedict. Many restaurants in town offer this unique dish, and it's sure to satisfy your appetite.
  • What are the best bed and breakfasts with parking in Chestertown, MD?

    Piney Grove Farm, Private Room W/bath: Walk To Washington College and Brampton 1860 are the best B&Bs with parking in Chestertown, MD.

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