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Check prices for these dates

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8 Aug - 10 Aug
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15 Aug - 17 Aug
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29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Browse Select Chestertown B&B

Rockwell Falls Inn and Wine Bar
Relax on the covered porch with wicker chairs and a glass table, surrounded by lush greenery and hanging flower baskets.

Rockwell Falls Inn and Wine Bar

3.5 star property
9.4 out of 10, Exceptional, (212)
"Beautiful room (Sunrise Suite), delicious breakfast, friendly staff, comfy porch for reading! Wish there could have been a few more choices for dinner food with our wine in the evening."
Rockwell Falls Inn and Wine Bar
The Fern Lodge
Relax by the water's edge in this serene outdoor seating area, complete with a fire pit and comfortable seating.

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (47)
"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 Fern Lodge
The Loft at The Remington
Interior

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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Top Chestertown Hotel Reviews

Lakefront Terrace Resort

Lakefront Terrace Resort

10/10 Excellent
"The pool is great for the kids, the breakfast and lunch at the bar are good and they don’t break the bank. Being able to walk down to the water and not worry about the kids terribly is always a plus. We love it. Hidden gem. "
Michael 4-night trip
Posted 12 hours ago
Lakefront Terrace Resort

Frequently asked questions

Searching for B&Bs in Chestertown?
If you're looking for something a little different than your standard hotel, a bed and breakfast could be the perfect alternative for your holiday. 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 right choice for your stay?
With attentive service, opportunities to mingle with other guests and of course a scrumptious breakfast, B&Bs provide a truly 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 hot tubs. The Loft at The Remington: 0.1 mi (0.1 km) from the city centre.
When is the best time to stay at a B&B in Chestertown?
When you're dreaming of a trip 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 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chestertown are January, March, November and December, with each month seeing an average of 33 cm 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 should 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?
You can map out your trip in and around Chestertown ahead of time with these transportation options. Fly into Glens Falls, NY (GFL-Floyd Bennett Memorial), which is located 23.6 mi (38 km) 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.