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This weekend

Compare 6 B&B in Chestertown with updated reviews, rates, and availability.

Restaurant
The Fern Lodge
3.5 star property
9.8 out of 10, Exceptional, (42)
"Paradise just simply heavenly. And so well appointed. Feel so at home"
The price is NT$19,081
per night
May 9 - May 10
The Fern Lodge
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
Porch
The Lamplight Inn B&B
3.5 star property
9.2 out of 10, Wonderful, (206)
"Everything is wonderful about the Lamplight Inn. The rooms, the food, the area, the atmosphere and especially the innkeepers Gene and Linda. The best people you could ever want to meet. We love it at this inn and will continue to go to it each and every year at least twice a year."
The Lamplight Inn B&B
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View from property
Ruah Bed & Breakfast
3.5 star property
8.6 out of 10, Excellent, (30)
"I liked the location's proximity to various venues planned for this wedding weekend. The owner's were engaging and very helpful"
Ruah Bed & Breakfast
Front of property
The Glens Falls Inn
3.0 star property
8.0 out of 10, Very Good, (40)
"I was utterly charmed by the decor, both the photos online and at the B&B when I arrived, but my stay was a huge disappointment. Granted, it was the off season, but there was none of the affability and personality that I tend to associate with B&Bs. The owners were MIA, so only the caretaker and her family were onsite. Breakfast consisted of store-bought, calorie-heavy muffins; the water in the dining room pitcher and electric kettle sat out unchanged; a film of dust covered the downstairs...
The Glens Falls Inn
Interior
The Loft at The Remington
3.5 star property
The Loft at The Remington
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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.

Other property types in Chestertown

Chestertown B&B information

Number of reviews
150
Accommodation
6 B&B
Lowest Price
NT$19,081
Highest Price
NT$19,081

Frequently asked questions

Searching for B&Bs in Chestertown?
If you’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 you’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. Alynn’s Butterfly Inn Bed & Breakfast: 5 rooms. Situated 8.2 mi (13.2 km) from the heart of Chestertown. Enjoy the free full breakfast and unique décor. Ruah Bed & Breakfast: 4 rooms. Located 17.1 mi (27.5 km) from the core of Chestertown. Enjoy the free full breakfast and library.
When is the best time to stay at a B&B in Chestertown?
When you’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 65°F, while the coldest months are January and February with an average of 25°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 you’d like to venture out around the area, you may want to rent a car for your trip.

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