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Check prices for these dates

Next weekend
7 Saf. - 9 Saf.
In two weeks
14 Saf. - 16 Saf.
In one month
28 Saf. - 2 Rab. I
In two months
28 Rab. I - 30 Rab. I

Compare B&B in Chestertown with updated reviews, rates, and availability.

The Fern Lodge
Room

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (45)
"We had such a great experience the first night so we moved our plans and stayed a second, next time we will definitely stay even longer."
The price is SARĀ 2,202
SARĀ 2,444 total
includes taxes & fees
4 Feb - 5 Feb
The Fern Lodge
Rockwell Falls Inn and Wine Bar
Front of property

Rockwell Falls Inn and Wine Bar

3.5 star property
9.2 out of 10, Wonderful, (209)
"It was a nice getaway. Beds were comfortable and rooms were spacious with hot tub and fireplace. Staff was friendly and very accommodating. Breakfast was awesome. "
Rockwell Falls Inn and Wine Bar
Alynn's Butterfly Inn Bed & Breakfast
Exterior

Alynn's Butterfly Inn Bed & Breakfast

3.5 star property
9.6 out of 10, Exceptional, (14)
"It was very nice, peaceful and the host & hostess did everything they could to make our time there a good memory"
Alynn's Butterfly Inn Bed & Breakfast
The Loft at The Remington
Exterior

The Loft at The Remington

3.5 star property
The Loft at The Remington
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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Other property types in Chestertown

Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain

10.0 out of 10, Exceptional, (106)
"A fantastic location for those looking to get away in the Adirondacks. Conveniently close to Chestertown, as well as many outdoor activities, Eagles Nest was an awesome location to stay at with friends and family. "
Eagles Nest at Loon Lake near Gore Mountain
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Great Room

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

10.0 out of 10, Exceptional, (57)
"Incredible place and stay, highly recommended!"
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Lakefront cabin with beautiful loft, game room, views, private dock

Lakefront cabin with beautiful loft, game room, views, private dock

9.2 out of 10, Wonderful, (35)
"Loved everything from the coffee maker to the views at this place. Fantastic!"
Lakefront cabin with beautiful loft, game room, views, private dock
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.

Frequently asked questions

Searching for B&Bs in Chestertown?
If youā€™re looking for something a little different than your standard hotel experience, a bed and breakfast could be a great option for your trip. If youā€™re hoping to spend some time walking along the water in Chestertown, Loon Lake Beach is worth a visit.
How do you know if a B&B is the best choice for your stay?
With attentive service, opportunities to meet other guests, and tasty breakfasts, B&Bs all have a one-of-a-kind setting.
What are the top B&Bs in Chestertown?
Here are some B&Bs in the surrounding area: The Fern Lodge: 5 rooms. 3.1 mi (4.9 km) from the heart of Chestertown. Enjoy the local cuisine breakfast and spa tubs. The Loft at The Remington: 0.1 mi (0.1 km) from the downtown core.
When is the best time to stay at a B&B in Chestertown?
When youā€™re dreaming of a stay in Chestertown, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 65Ā°F, while the coldest months are January and February with an average of 25Ā°F. The snowiest months in Chestertown are January, March, November, and December, with each month seeing an average of 13 inches of snowfall.
What is there to do in Chestertown?
When you want to spend some time in the great outdoors, Loon Lake Beach and Friends Lake are some notable spots. You might put Loon Lake and Hudson River on your list if you want to see more of the area.
How can I get to and around Chestertown?
Mapping out your trip in and around Chestertown is easy with these transportation options. Fly into Glens Falls, NY (GFL-Floyd Bennett Memorial), which is located 23.6 mi (38 km) away from the heart of the city. If youā€™d like to venture out around the area, you may want to rent a car for your trip.