Photo by Julie Miller

Find a Bed and Breakfast in Chestertown

Q: 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. Situated 8.2 mi (13.2 km) from the heart of Chestertown. Enjoy the free full breakfast and unique décor. Ruah Bed & Breakfast : 4 rooms. Located 17.1 mi (27.5 km) from the core of Chestertown. Enjoy the free full breakfast and library.

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"The house is the perfect combination of woodsy and modern. Most of the wooden furniture has been beautifully hand made with creative design. The high celings in the main family room are also made of gorgeous wood. There is a real fireplace that we unfortunately did not use because it was too warm. Comfy leather recliners and a 75 inch TV. The kitchen is open to the main room with a peninsula to sit at with stools. Modern appliances, all the kitchen ware you could possibly need, clean and new....

"Clean property. Kids enjoyed games in basement."

"We loved the days we stayed there, beautiful environment, very nice view. Be careful with the mosquitos, they came out in the evening."

Chestertown B&B information

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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. Situated 8.2 mi (13.2 km) from the heart of Chestertown. Enjoy the free full breakfast and unique décor. 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 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.