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Find Chestertown Bed And Breakfast

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Compare B&B in Chestertown with updated reviews, rates, and availability.

Other property types in Chestertown

Fridge, microwave, oven, stovetop
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
10.0 out of 10, Exceptional, (38)
"The place was amazing!!! So clean and had everything you need to stay away from home!!! Our do Oliver especially loved playing with Ruby and Pearl!!!"
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Property grounds
Peaceful Lakeside Retreat with Private Beach
9.4 out of 10, Exceptional, (9)
"We stay in Lake George every year for Labor Day. Although we love it, I wanted something more peaceful. This place was amazing. Very clean, quiet and lits to do right there on the property. We ate at George Henry's, the food was fantastic. Its only about a 20 min drive to Lake George, so we got the best of both worlds 😊 Would love to come back again next year!"
Peaceful Lakeside Retreat with Private Beach
Exterior
Private child-friendly home with game room, high-speed WiFi, and wraparound deck
9.8 out of 10, Exceptional, (48)
"Clean property. Kids enjoyed games in basement."
Private child-friendly home with game room, high-speed WiFi, and wraparound deck
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.

Chestertown B&B information

Number of reviews
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B&B
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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.

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