Photo by Julie Miller

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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 5 B&B in Chestertown with updated reviews, rates, and availability.

The Fern Lodge
Lake view

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 AED 2,156
AED 2,393 total
includes taxes & fees
7 May - 8 May
The Fern Lodge
Rockwell Falls Inn and Wine Bar
Hiking

Rockwell Falls Inn and Wine Bar

3.5 star property
9.2 out of 10, Wonderful, (210)
"Kind and friendly staff, Beautiful room and an amazing breakfast. What more could you ask?"
Rockwell Falls Inn and Wine Bar
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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Other property types in Chestertown

Trout House Village Resort
Luxury Cabin, 1 Bedroom, Lake View | Living area | 42-inch Smart TV with digital channels, DVD player, streaming services

Trout House Village Resort

3.0 star property
10.0 out of 10, Exceptional, (11)
"Absolutely wonderful place and super friendly staff "
The price is AED 531
AED 681 total
includes taxes & fees
7 May - 8 May
Trout House Village Resort
Walk to Million Dollar Beach from this awesome Cottage!
Exterior

Walk to Million Dollar Beach from this awesome Cottage!

10.0 out of 10, Exceptional, (151)
"Had a great time good location and plenty of room."
Walk to Million Dollar Beach from this awesome Cottage!
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
Interior

ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

10.0 out of 10, Exceptional, (82)
"Amazing"
The price is AED 569
AED 840 total
includes taxes & fees
7 May - 8 May
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
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 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 hot 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 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.