Bed and Breakfast in Chestertown, MD

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7 nights
2
1
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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!

Walk To Historic Chestertown: Dog-friendly Retreat - Chestertown, MD
No reviews

Walk To Historic Chestertown: Dog-friendly Retreat

house, Chestertown
This dog-friendly residence in Chestertown is situated within walking distance of the historic town centre, with New Castle Airport located 72 kilometres away.
This property offers 90 square metres of living space, accommodating up to 11 guests with two bathrooms, air conditioning, complimentary WiFi, and on-site parking, plus a fully equipped kitchen.
Owl Cottage -
Cozy, Private & Walkable To Town - Chestertown, MD
10 66 reviews

Owl Cottage - Cozy, Private & Walkable To Town

house, Chestertown
Owl Cottage is a renovated carriage house located in the centre of Chestertown, just a short walk from the historic district and waterfront. This charming cottage offers a unique blend of historic charm and modern convenience.
The property has a unique layout with a ground floor bedroom, a second floor living/kitchen area with a bathroom, and a third floor loft with a queen-sized bed. The cottage comfortably sleeps up to four guests and includes a private garden, patio, and pet-friendly amenities.
Lovely Home In Chestertown -  Free Ev Charging For Guests - Chestertown, MD
10 29 reviews

Lovely Home In Chestertown - Free Ev Charging For Guests

apartment, Kingstown
This Chestertown holiday home is situated within a 2.4km walk of Kingstown Park, the Historical Society of Kent County Maryland, and the Garfield Center for the Arts, with Washington College and River Arts Chestertown also within 1.6km.
The 134 square metre property boasts three bedrooms, three bathrooms, sleeps six guests, and includes a fully equipped kitchen, free Wi-Fi, a private patio, and is within walking distance of several attractions.
Bright, New Apartment In The Heart Of Chestertown - Chestertown, MD
10 141 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.

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 first-time visit, you'll want to see the historic downtown area, with its charming shops and restaurants. The Chestertown Riverwalk is a lovely spot to stroll and take in the scenery. You can also visit the beautiful campus of Washington College, founded in 1783.
  • 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 four distinct seasons. Summers are warm and humid, with temperatures averaging around 25 degrees Celsius. Winters are mild, with average temperatures around 5 degrees Celsius. Spring and autumn are beautiful, with mild temperatures and vibrant foliage.
  • 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 enjoy the outdoors. You can go kayaking or canoeing on the Chester River, hike or bike on the Chestertown Greenway, or visit the nearby Eastern Neck National Wildlife Refuge for birdwatching.
  • 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 local breakfast specialties can you enjoy in Chestertown, MD region?

    Chestertown is known for its delicious local breakfast options. Try the famous 'Chesapeake Bay Crab Cake Benedict' at the Mainstay Restaurant or enjoy a classic American breakfast at the Chesapeake Inn. You can also find fresh pastries and coffee at the local bakery, The Coffee Cup.
  • 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 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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