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Check prices for these dates

Next weekend
21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov
In one month
12 Dec - 14 Dec
In two months
9 Jan - 11 Jan
Lake
Inn at Huntingfield Creek

Inn at Huntingfield Creek

3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (56)
"Wonderful! Quiet and relaxing anniversary! Pool was great, dock is beautiful, room was clean, comfortable and spacious. Water bottles and cookies are such a nice touch. Breakfast was delicious. Amazing property and genuine hosts. Thank you"
United States
Cristy
Inn at Huntingfield Creek
Front of property
Flag House Inn

Flag House Inn

3.5 star property
Historic District
9.4 out of 10, Exceptional, (80)
"Overpriced for what it offered. $500+ for a single night at the property sans breakfast or parking. Room itself was small with no real historic flair or charm. Found a used washcloth on the floor housekeeping had overlooked. To check in during peak hours we had to call hotel staff (attending to other properties when we arrived) in order to get access to the room. If this property were about $200 less expensive, I would have zero complaints, but to spend that amount of money I expected way...
United States
Kathy
The price is HK$812
HK$926 total
includes taxes & fees
12 Nov - 13 Nov
Flag House Inn
Terrace/patio
Vandiver Inn

Vandiver Inn

3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (528)
"Lovely inn & receptionist was wonderful. "
United States
Deborah
Vandiver Inn
Interior
Charming bed & breakfast in Smyrna with AC, WiFi. Enjoy

Charming bed & breakfast in Smyrna with AC, WiFi. Enjoy

Smyrna
10.0 out of 10, Exceptional, (1)
"Overall great place. Nice neighborhood. Very spacious and clean living area. Loved having the pool table and all the games. Lisa is a great host and the breakfast is delicious. "
United States
David W.
The price is HK$1,168
HK$3,643 total
includes taxes & fees
13 Nov - 14 Nov
Charming bed & breakfast in Smyrna with AC, WiFi. Enjoy
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

Hampton Inn Baltimore Bayview Campus

Hampton Inn Baltimore Bayview Campus

10/10 Excellent
"This entire property was spotless, the lobby, room and common areas are comfortable and very clean. The indoor pool was the highlight of our visit and the breakfast spread was excellent. The staff we spoke with were all friendly and helpful. We will happily stay here again!"
Audrey 1-night trip
Posted 1 day ago
Hampton Inn Baltimore Bayview Campus

Find out more about Chestertown

Chestertown B&B information

Number of reviews
598
Accommodation
8 B&B
Lowest Price
HK$926
Highest Price
HK$3,643

Frequently asked questions

Searching for B&Bs in Chestertown?
If you're interested in something a little more offbeat than the traditional hotel experience, a stay at a bed and breakfast could be a great option for your holiday. 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 should you consider a B&B over a traditional hotel room?
Every B&B has a unique charm — whether it's a comfy common area with a fireplace or a sunlit breakfast nook to enjoy your morning cup of coffee, the tiny details are what make bed and breakfasts the perfect escape.
What are the best B&Bs in Chestertown?
Here are some B&Bs in the area: Inn at Huntingfield Creek: 12 rooms. Situated 11.3 mi (18.2 km) from the heart of Chestertown. Enjoy the local cuisine breakfast and Jetted bath. Inn at Haven Harbour: 24 rooms. 11 mi (17.7 km) from the city centre. Enjoy the on-site dining and outdoor pool.
When is the best time to book my B&B in Chestertown?
When you're planning your escape to Chestertown, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
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 visit. You should put Rolphs Wharf Marina and Chesapeake Bay on your list if you want to see more of the area.
How can I get to and around Chestertown?
You can plan your excursions 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) away from the heart of the city. Otherwise, look 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, consider renting a car to explore more sights.

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