Search B&B in Chestertown

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
20 Feb - 22 Feb
In two weeks
27 Feb - 1 Mar
In one month
13 Mar - 15 Mar
In two months
10 Apr - 12 Apr

Our top choices for Chestertown bed & breakfast

Lake view

The Fern Lodge

The Fern Lodge
3.5 star property
Chestertown
10.0 out of 10, Exceptional, (52 reviews)
"I cannot say enough good things about the Fern Lodge. Beautiful atmosphere, wonderful host. Will be returning! "
United States
Morgan
The Fern Lodge
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

Six Flags Great Escape Lodge & Indoor Waterpark

Six Flags Great Escape Lodge & Indoor Waterpark

10/10 Excellent
"Great "
john 1-night trip
Posted 4 days ago
Six Flags Great Escape Lodge & Indoor Waterpark

Find out more about Chestertown

Chestertown B&B information

Number of reviews
47
Accommodation
4 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. 4-bedroom bed & breakfast in distinct North Creek, with a rustic cozy cabin feel: Situated 9.8 mi (15.8 km) from the heart of Chestertown.
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.

Explore a world of travel with Expedia