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!

Down By The River - Chestertown, MD
9.9 61 reviews

Down By The River

apartment, Chestertown
This charming apartment is located just a short walk from the historic centre of Chestertown, offering stunning views of the Chester River. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The apartment has three bedrooms and two bathrooms, comfortably accommodating up to 10 guests. It features a fully equipped kitchen, a garden, a fire pit, and access to kayaking on the river, making it an ideal choice for families or groups looking for a relaxing and enjoyable stay.
Walking Distance To Marinas & Main St! - Chestertown, MD
9.8 128 reviews

Walking Distance To Marinas & Main St!

house, Rock Hall
This waterfront property is a 15-minute walk from Rock Hall Harbour, The Mainstay, and Waterman’s Museum, offering a peaceful setting close to the town’s attractions. The property has received excellent ratings for its cleanliness, location, and overall user experience.
This three-bedroom house comfortably accommodates eight guests. Enjoy the convenience of a fully equipped kitchen, a fireplace, and a spacious garden with barbecue grills, perfect for relaxing evenings.
Oyster Cottage  - Walk To Shops , Mainstay Music Venue And The Bay! - Chestertown, MD
9.6 14 reviews

Oyster Cottage - Walk To Shops , Mainstay Music Venue And The Bay!

cottage, Rock Hall
Oyster Cottage is a charming holiday home situated just a short walk from the waterfront in Rock Hall, offering easy access to shops, restaurants, and entertainment. The cottage consistently receives excellent reviews from guests, highlighting its comfortable and convenient location.
The property features two bedrooms, accommodating up to seven guests, making it ideal for families or groups of friends. The cottage offers a range of amenities including a fully equipped kitchen, a private garden, and a patio for outdoor dining, ensuring a relaxing and enjoyable stay.
2 Beds, 2.5 Baths - Perfect Downtown Location - Chestertown, MD
10 124 reviews

2 Beds, 2.5 Baths - Perfect Downtown Location

apartment, Chestertown
This charming apartment is situated in the heart of historic Chestertown, just a short walk from the town's shops, restaurants and Washington College. It has received excellent ratings for its location, cleanliness and overall user experience.
The apartment has two bedrooms and two bathrooms, comfortably accommodating up to four guests. It is well-equipped with modern amenities, including a fully fitted kitchen, high-speed internet, air conditioning, a private garden and parking.

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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