A waterfront town with a pier, dock, and several buildings.

Find a Bed and Breakfast in Chestertown from CA $690

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Check prices for these dates

Next weekend
Jul 31 - Aug 2
In two weeks
Aug 7 - Aug 9
In one month
Aug 21 - Aug 23
In two months
Sep 18 - Sep 20

Our top choices for Chestertown bed & breakfast

Lake view

The Fern Lodge

The Fern Lodge
3.5 star property
Chestertown
9.8 out of 10, Exceptional, (57 reviews)
"Staff is great,friendly and helpful Loved our stay. Place is beautiful"
United States
robert
The price is CA $622
CA $690 total
includes taxes & fees
Jul 22 - Jul 23
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.
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Top Chestertown Hotel Reviews

Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites

10/10 Excellent
"The rooms were basic but clean. Great playground for the kids and the covered swimming pool was a real plus. Also walkable to most places and a short ride to a lovely beach"
Sheila 4-night trip
Posted less than an hour ago
Adirondack Retreat Inn & Suites

Find out more about Chestertown

Chestertown B&B information

Number of reviews
57
Accommodation
3 B&B
Lowest Price
CA $690
Highest Price
CA $690

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.

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