An aerial view of a town with a river, buildings, and surrounding greenery.

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Chestertown bed & breakfast

A boat deck with a white bench and a view of a calm lake and distant trees.

1. Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (74 reviews)
"The offsite property was perfect for my husband and I to enjoy the town and walk everywhere! Dinner at Waterman’s was a 12 minute walk, and drinks at the brewery was less then a minute walk."
United States
Kat
The price is ₩187,302
₩207,916 total
includes taxes & fees
Nov 16 - Nov 17
Inn at Huntingfield Creek
A Victorian-style building with a porch, outdoor seating, and a sign for Vandiver Inn.

2. Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.6 out of 10, Exceptional, (580 reviews)
"Absolutely LOVED our stay here! It is such a cute, unique place to stay and we loved the fun, friendly atmosphere. It was lively during the day, yet peaceful and quiet at night. The complimentary breakfast was also so nice! The room was wonderful and clean. The staff were so helpful, friendly, and welcoming. Definitely recommend staying here!"
United States
Samantha
The price is ₩203,330
₩227,730 total
includes taxes & fees
Dec 1 - Dec 2
Vandiver Inn
A room with a dark blue wall, a fireplace with lit candles, a leather armchair, and a bookshelf with decorative items.

3. Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (101 reviews)
"Charming and picturesque house steps from all of the best things about Annapolis."
United States
Thomas
The price is ₩291,253
₩332,026 total
includes taxes & fees
Nov 16 - Nov 17
Flag House Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Positives included being close to the sites and Annapolis history, a very attentive hotel and valet parking staff with quick response to requests. Negatives included a noisy refrigerator, no microwave and a restaurant nearby playing loud music into the late evening. The only real choice was using valet parking and it was very expensive. Sometimes historic just means old. The rooms could use some updating."
Gerald 3-night trip
Posted 13 hours ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown B&B information

Number of reviews
580
Accommodation
6 B&B
Lowest Price
₩207,916
Highest Price
₩332,026

Frequently asked questions

Searching for B&Bs in Chestertown?
If you're looking for something a little quirkier than your standard hotel experience, a stay at a bed and breakfast might be the perfect option for your trip. While you're enjoying your trip to Chestertown, Chestertown Dog Park and Urieville Park are perfect spots to get in some fresh air and greenery.
Why choose B&Bs instead of traditional hotels?
Every B&B has a unique charm. Whether it's a picturesque garden or a beautiful dining room, the little details are what make bed and breakfasts a home away from home.
What are the best B&Bs in Chestertown?
Here are some B&Bs in the area: Great Oak Manor: 12 rooms. 7.9 mi (12.7 km) from the heart of Chestertown. Enjoy the free full breakfast and private beach. Inn at Huntingfield Creek: 12 rooms. 11.3 mi (18.2 km) from the heart of downtown. Enjoy the local cuisine breakfast and jetted tubs. Inn at Haven Harbour: 24 rooms. Located 11 mi (17.7 km) from the core of Chestertown. Enjoy the onsite dining and outdoor pool.
When should I book my B&B in Chestertown?
When you're planning your stay in Chestertown, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What is there to do in Chestertown?
When you want to explore some cultural attractions on your trip, Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater are worthy sites to check out. You might put Chestertown Historic District and Rolphs Wharf Marina on your list if you want to see more of the area.
How can I get to and around Chestertown?
You can map out your trip in and around Chestertown ahead of time with these transportation options. Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the heart of the city. You can also search for flights into Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.

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