The Brampton Bed and Breakfast Inn is located on Maryland's Eastern Shore, a short distance from Chestertown's centre and Washington College, offering a peaceful escape in the beautiful Maryland countryside. The B&B has consistently received excellent ratings for its location, cleanliness, and overall user experience. This charming 19th-century inn can accommodate up to two guests in its single bedroom and bathroom. Enjoy a range of amenities including a spa, a terrace, a garden, and a restaurant, perfect for a relaxing and enjoyable stay.
10 1 review
Chestertown, MD
03/07 – 08/07
NZ$406/nighttotal: NZ$2030 (5 )
Dog-friendly Getaway Near Large Park And Dog Park
1 2
B&B , Chestertown
This 3-bedroom flat is located in a peaceful residential area of Chestertown, offering convenient access to local shops and dining within 1 kilometre. This pet-friendly accommodation sleeps up to six guests and features a private entrance, a walk-in bathroom, a kitchenette with a microwave and mini-fridge, and a gas fireplace.
9.9 99 reviews
Chestertown, MD
20/07 – 23/07
NZ$353/nighttotal: NZ$1059 (3 )
Historic Downtown Garden Oasis With Private Patio
1 2
B&B , Chestertown
108Annex, a guesthouse in Chestertown's Arts & Entertainment District, offers a prime location steps from downtown restaurants and shops. This self-catering apartment features a queen bedroom with en-suite bathroom, a living/dining area, a well-equipped kitchenette with coffee maker, and a private patio overlooking a garden; it sleeps two guests and includes air conditioning, parking, and keyless entry.
10 124 reviews
Chestertown, MD
20/07 – 23/07
NZ$229/nighttotal: NZ$687 (3 )
House On The Hill - Historic Private Second Floor
1 2
B&B , Chestertown
This charming guesthouse is located in historic Chestertown, just a short walk from the town centre and a 3-kilometre drive from the waterfront. It has consistently received excellent ratings for its location, cleanliness, and overall guest experience. The property offers a private second-floor suite with two bedrooms, a bathroom, and a sitting area, accommodating up to four guests. Guests can enjoy a garden with chairs and a fire pit, a mini-fridge, a coffee maker, and local recommendations from the friendly hosts.
9.7 132 reviews
Chestertown, MD
03/07 – 08/07
NZ$816/nighttotal: NZ$4080 (5 )
Inn At Huntingfield Creek
1 2
B&B , Rock Hall
The Inn at Huntingfield Creek is located in Rock Hall, Maryland, just 92 miles from Baltimore and 63 miles from Annapolis, making it a convenient base for exploring the Chesapeake Bay. The Inn has consistently received excellent ratings for its cleanliness, location, and overall experience. The guest house offers a comfortable and spacious room with a private bathroom. Guests can enjoy a refreshing dip in the seasonal outdoor pool, relax in the shared lounge, or take advantage of the free WiFi. A full English/Irish breakfast is provided each morning, and the Inn also offers cycling and canoeing opportunities for those wanting to explore the surrounding area.
Best Chestertown, MD bed and breakfasts with breakfast included
10 1 review
Chestertown, MD
03/07 – 08/07
NZ$406/nighttotal: NZ$2030 (5 )
Dog-friendly Getaway Near Large Park And Dog Park
1 2
B&B , Chestertown
This 3-bedroom flat is located in a peaceful residential area of Chestertown, offering convenient access to local shops and dining within 1 kilometre. This pet-friendly accommodation sleeps up to six guests and features a private entrance, a walk-in bathroom, a kitchenette with a microwave and mini-fridge, and a gas fireplace.
Best Chestertown, MD bed and breakfasts with a garden
10 124 reviews
Chestertown, MD
20/07 – 23/07
NZ$229/nighttotal: NZ$687 (3 )
House On The Hill - Historic Private Second Floor
1 2
B&B , Chestertown
This charming guesthouse is located in historic Chestertown, just a short walk from the town centre and a 3-kilometre drive from the waterfront. It has consistently received excellent ratings for its location, cleanliness, and overall guest experience. The property offers a private second-floor suite with two bedrooms, a bathroom, and a sitting area, accommodating up to four guests. Guests can enjoy a garden with chairs and a fire pit, a mini-fridge, a coffee maker, and local recommendations from the friendly hosts.
9.9 99 reviews
Chestertown, MD
20/07 – 23/07
NZ$353/nighttotal: NZ$1059 (3 )
Historic Downtown Garden Oasis With Private Patio
1 2
B&B , Chestertown
108Annex, a guesthouse in Chestertown's Arts & Entertainment District, offers a prime location steps from downtown restaurants and shops. This self-catering apartment features a queen bedroom with en-suite bathroom, a living/dining area, a well-equipped kitchenette with coffee maker, and a private patio overlooking a garden; it sleeps two guests and includes air conditioning, parking, and keyless entry.
Frequently asked questions about bed and breakfast in Chestertown, MD
What outdoor activities can visitors enjoy in and around Chestertown, MD?
Chestertown is a great place for outdoor activities. You can go kayaking or canoeing on the Chester River, hiking or biking on the Chestertown Greenway, or fishing from the docks. There are also several parks and gardens in the area, such as the Wilmer Park and the Chestertown Garden Club.
What are the best bed and breakfasts in Chestertown, MD?
Best Chestertown, MD bed and breakfasts with parking
9.9 99 reviews
Chestertown, MD
20/07 – 23/07
NZ$353/nighttotal: NZ$1059 (3 )
Historic Downtown Garden Oasis With Private Patio
1 2
B&B , Chestertown
108Annex, a guesthouse in Chestertown's Arts & Entertainment District, offers a prime location steps from downtown restaurants and shops. This self-catering apartment features a queen bedroom with en-suite bathroom, a living/dining area, a well-equipped kitchenette with coffee maker, and a private patio overlooking a garden; it sleeps two guests and includes air conditioning, parking, and keyless entry.
10 124 reviews
Chestertown, MD
20/07 – 23/07
NZ$229/nighttotal: NZ$687 (3 )
House On The Hill - Historic Private Second Floor
1 2
B&B , Chestertown
This charming guesthouse is located in historic Chestertown, just a short walk from the town centre and a 3-kilometre drive from the waterfront. It has consistently received excellent ratings for its location, cleanliness, and overall guest experience. The property offers a private second-floor suite with two bedrooms, a bathroom, and a sitting area, accommodating up to four guests. Guests can enjoy a garden with chairs and a fire pit, a mini-fridge, a coffee maker, and local recommendations from the friendly hosts.
Best Chestertown, MD bed and breakfasts with air conditioning
10 1 review
Chestertown, MD
03/07 – 08/07
NZ$406/nighttotal: NZ$2030 (5 )
Dog-friendly Getaway Near Large Park And Dog Park
1 2
B&B , Chestertown
This 3-bedroom flat is located in a peaceful residential area of Chestertown, offering convenient access to local shops and dining within 1 kilometre. This pet-friendly accommodation sleeps up to six guests and features a private entrance, a walk-in bathroom, a kitchenette with a microwave and mini-fridge, and a gas fireplace.
10 124 reviews
Chestertown, MD
20/07 – 23/07
NZ$229/nighttotal: NZ$687 (3 )
House On The Hill - Historic Private Second Floor
1 2
B&B , Chestertown
This charming guesthouse is located in historic Chestertown, just a short walk from the town centre and a 3-kilometre drive from the waterfront. It has consistently received excellent ratings for its location, cleanliness, and overall guest experience. The property offers a private second-floor suite with two bedrooms, a bathroom, and a sitting area, accommodating up to four guests. Guests can enjoy a garden with chairs and a fire pit, a mini-fridge, a coffee maker, and local recommendations from the friendly hosts.
9.9 99 reviews
Chestertown, MD
20/07 – 23/07
NZ$353/nighttotal: NZ$1059 (3 )
Historic Downtown Garden Oasis With Private Patio
1 2
B&B , Chestertown
108Annex, a guesthouse in Chestertown's Arts & Entertainment District, offers a prime location steps from downtown restaurants and shops. This self-catering apartment features a queen bedroom with en-suite bathroom, a living/dining area, a well-equipped kitchenette with coffee maker, and a private patio overlooking a garden; it sleeps two guests and includes air conditioning, parking, and keyless entry.
