Photo by Julie Miller

Search B&B 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

Compare 5 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 SAR 2,249
SAR 2,496 total
includes taxes & fees
6 Jan - 7 January 2025
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, (208)
"Kind and friendly staff, Beautiful room and an amazing breakfast. What more could you ask?"
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
4-bedroom bed & breakfast in distinct North Creek, with a rustic cozy cabin feel
Interior

4-bedroom bed & breakfast in distinct North Creek, with a rustic cozy cabin feel

4-bedroom bed & breakfast in distinct North Creek, with a rustic cozy cabin feel
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.
Don't see what you're looking for?
See all available properties in Chestertown
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chestertown

Peaceful Lakeside Retreat with Private Beach
Lake

Peaceful Lakeside Retreat with Private Beach

9.2 out of 10, Wonderful, (17)
"It was clean, nicely decorated, everything was new and in working order. Would suggest adding some face/wash cloths and top sheet for bed. Also, bed was comfortable but squeaked every time you made a move. All in all nice property and enjoyed our time :)"
Peaceful Lakeside Retreat with Private Beach
Cozy retreat with fireplace, kayaks, and shared beach/pond access

Cozy retreat with fireplace, kayaks, and shared beach/pond access

9.0 out of 10, Wonderful, (16)
"Beautiful place wood location"
Cozy retreat with fireplace, kayaks, and shared beach/pond access
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, (54)
"It’s a wonderful place beautiful fireplace cozy cabin. Bed is so comfy. Just know there is only one bathroom but it’s big and nice. Worth the stay. "
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
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 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. 8.2 mi (13.2 km) from the heart of downtown. Enjoy the free full breakfast and unique décor. 4-bedroom bed & breakfast in distinct North Creek, with a rustic cozy cabin feel: Located 9.8 mi (15.8 km) from the core of Chestertown.
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.