Best B&Bs in Chestertown
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Great deal
Gramercy Mansion
- In-room breakfast
- Free parking
- VIP check-in/ -out
- Air conditioning
- Tennis court
- Outdoor swimming pool
The elegant Gramercy Mansion Stevenson hotel, situated approximately 10 minutes' drive from The Passage, offers meeting rooms for corporate guests. The 4-star bed & breakfast offers private car parking on site and an outdoor swimming pool.
Guests are invited to the onsite outdoor bar to unwind with a drink.
Gramercy Mansion
- In-room breakfast
- Free parking
- VIP check-in/ -out
- Air conditioning
- Tennis court
- Outdoor swimming pool
Gramercy Mansion
The elegant Gramercy Mansion Stevenson hotel, situated approximately 10 minutes' drive from The Passage, offers meeting rooms for corporate guests. The 4-star bed & breakfast offers private car parking on site and an outdoor swimming pool.
Guests are invited to the onsite outdoor bar to unwind with a drink.
Bed and Breakfast Downtown Chestertown
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Best-rated
1840S Carrollton Inn
- In-room breakfast
-
Car park
US$ 10 per day
- 24-hour reception
- Air conditioning
- Spa & wellness centre
- Sun terrace
Located about 5 minutes' walk from Star Spangled Banner Flag House 1812 Museum, the comfortable 1840S Carrollton Inn Baltimore gives easy access to various tourist attractions. This 4-star luxurious bed & breakfast has views of the courtyard and features high-speed Internet access in public areas.
This Baltimore hotel is right around the corner from Bluegrass Etc, which serves delectable meals.
1840S Carrollton Inn
- In-room breakfast
-
Car park
US$ 10 per day
- 24-hour reception
- Air conditioning
- Spa & wellness centre
- Sun terrace
1840S Carrollton Inn
Located about 5 minutes' walk from Star Spangled Banner Flag House 1812 Museum, the comfortable 1840S Carrollton Inn Baltimore gives easy access to various tourist attractions. This 4-star luxurious bed & breakfast has views of the courtyard and features high-speed Internet access in public areas.
This Baltimore hotel is right around the corner from Bluegrass Etc, which serves delectable meals.
Romantic Bed and Breakfast in Chestertown
George Brooks House B&B
- In-room breakfast
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Saltwater pool
Guests of George Brooks House B&B Saint Michaels can visit the Chesapeake Bay Maritime Museum, situated 20 minutes' walk away. This comfortable bed & breakfast features an outdoor swimming pool with a hot tub and a pool fence.
Offering international dishes, Stars Restaurant is situated within a few blocks of this Saint Michaels hotel.
George Brooks House B&B
- In-room breakfast
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Saltwater pool
George Brooks House B&B
Guests of George Brooks House B&B Saint Michaels can visit the Chesapeake Bay Maritime Museum, situated 20 minutes' walk away. This comfortable bed & breakfast features an outdoor swimming pool with a hot tub and a pool fence.
Offering international dishes, Stars Restaurant is situated within a few blocks of this Saint Michaels hotel.
Are you in a hurry?
Here is a quick list of Bed and Breakfast in Chestertown, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Gramercy Mansion |
9.5 / 10 (42 Reviews) |
From 192$ | |
| 1840S Carrollton Inn |
9.5 / 10 (224 Reviews) |
From 235$ | |
| George Brooks House B&B |
6.8 / 10 (10 Reviews) |
From 210$ |
Frequently Asked Questions
Which boutique bed & breakfasts in Chestertown offer a romantic atmosphere?
The George Brooks House B&B and Gramercy Mansion both create charming romantic experiences. You can enjoy luxurious rooms with historic decor and gourmet breakfasts tailored for couples.
Plan your stay during the off-peak season in November for lower rates and cozy environments.
What historic bed & breakfasts in Chestertown provide unique local character?
The 1840S Carrollton Inn and George Brooks House B&B feature distinctive historic charm with period furnishings. Their rich backgrounds enhance your stay with interesting stories and architecture.
Schedule a tour of the nearby Chesapeake Bay Maritime Museum, just a short bike ride from these inns.
Which bed & breakfasts in Chestertown are pet-friendly?
George Brooks House B&B is a pet-friendly option, welcoming guests with dogs. This charming place features serene gardens and outdoor spaces for walking pets.
Check for designated pet-friendly rooms when booking to ensure a smooth stay with your furry friend.
Are there any romantic getaways near Chestertown's historic district?
Both Gramercy Mansion and George Brooks House B&B offer romantic getaways close to historic sites. Their beautiful settings and thoughtful amenities make for perfect escapes.
Visit in April during the Chestertown Tea Party for a unique, local event that adds to the romantic ambiance.
Which Chestertown bed & breakfasts are ideal for a quiet retreat?
The George Brooks House B&B and Gramercy Mansion provide peaceful environments surrounded by gardens. These locations are also near outdoor activities like kayaking and biking.
Consider visiting during weekdays to avoid weekend crowds and experience tranquility.
What bed & breakfasts in Chestertown have unique themed rooms?
Gramercy Mansion is known for its exquisitely decorated rooms with historic themes. Each room tells a story and offers a unique experience.
Book the 'Garden Room' for stunning views and direct access to the outdoor gardens.
Which bed & breakfasts in Chestertown offer great breakfast options?
George Brooks House B&B and Gramercy Mansion both serve generous and delicious breakfasts. Enjoy homemade meals made from local ingredients during your stay.
Try to arrive early for breakfast to savor the seasonal specialties before they sell out.
What unique local events should I plan for when visiting Chestertown?
The Chestertown Tea Party is a must-see event in May, showcasing colonial reenactments and local artisans. This fun event includes food, music, and shopping opportunities.
Book a one-night stay at local bed & breakfasts like the George Brooks House B&B for easy access to the event.
How can I explore Chestertown's local history?
Visit the Historical Society of Kent County to learn about the town's rich past. Guided walking tours are also available for a more personal experience.
Plan your visits during guided tour times for insightful stories and access to hidden historical gems.
How many days should I spend in Chestertown?
A two to three-day stay is ideal to explore local attractions, attend events, and enjoy the charming atmosphere. Fantastic dining and sightseeing await you in the area.
Stay at Gramercy Mansion for its proximity to key sights and tranquil surroundings, perfect for short stays.