Photo by Julie Miller

Search Bed and Breakfasts in Chestertown

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Browse Select Chestertown B&B

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 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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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
Don't see what you're looking for?
See all available properties in Chestertown
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
151
Accommodation
6 B&B
Lowest Price
Highest Price

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. 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 decor. 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 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.

Chestertown Hotel Reviews
Expedia verified reviews

Fairfield Inn & Suites by Marriott Queensbury Glens Falls/Lake George Area

Fairfield Inn & Suites by Marriott Queensbury Glens Falls/Lake George Area

5/5 Excellent
"Property was clean and well-maintained, surroundings were quiet and the breakfast was well-stocked and satisfying."
A verified traveller stayed at Fairfield Inn & Suites by Marriott Queensbury Glens Falls/Lake George Area
Posted 3 days ago
Fairfield Inn & Suites by Marriott Queensbury Glens Falls/Lake George Area