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2026-11-09
2026-11-10
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Family Hotels in Chestertown

Friends Lake Inn

963 Friends Lake Rd, Chestertown, United States Show map

The 5-star Friends Lake Inn Chestertown, located 2.5 km from Loon Lake Public Beach, boasts a swimming pool. Featuring 20 rooms with views of the lake, this elegant inn is about 10 minutes by car… More

From US$ 115 Book Now

The Lodge At Loon Lake

5381 State Route 8, Chestertown, United States Show map

Located within 25 minutes' walk of Loon Lake, the 2-star The Lodge At Loon Lake Chestertown hotel offers amenities such as a sundeck, a picnic area, and a golf course. Featuring a private beach area,… More

From US$ 159 Book Now

Pine'S Way Camp

Chestertown, United States Show map

Located within 7 km of Rustic Charm Gift Shop, the 4-bedroom Pine'S Way Camp Villa Chestertown provides access to various tourist attractions in the vicinity. More

From US$ 592 Book Now

Around The Mountains

89 Mountain Path, Chestertown, United States Show map

Offering a location 3.2 km from Burnt Ridge Quad, Around The Mountains Villa Chestertown gives access to various tourist spots in the area. More

From US$ 565 Book Now

Moonbeams & Fireflies

Chestertown, United States Show map

Situated 4.4 km from Loon Lake, the 5-bedroom Moonbeams & Fireflies Villa Chestertown entices guests to explore various tourist attractions in the area. More

From US$ 615 Book Now

Riverside Bliss

41 East Hudson River Drive, Chestertown, United States Show map

Situated 4.5 km from Gore Mountain Farms Alpaca, the 3-bedroom Riverside Bliss Chestertown villa provides access to numerous tourist attractions in the area. More

From US$ 629 Book Now

Basic Adirondack Camp

Chestertown, United States Show map

The 3-bedroom Basic Adirondack Camp Villa Chestertown offers proximity to nearby tourist spots, such as Loon Lake Public Beach, situated approximately 25 minutes' walk away. More

From US$ 354 Book Now

Hideaway Chalet

Chestertown, United States Show map

Staying at the 3-bedroom Hideaway Chalet Chestertown, guests can easily reach Rustic Charm Gift Shop, located approximately 6 km away. Offering horse riding tours, the Chestertown villa can… More

From US$ 401 Book Now

Whit'S End

Chestertown, United States Show map

Staying at the 4-bedroom Whit'S End Villa Chestertown, guests can visit view, which is nearly a 10-minute drive away. More

From US$ 334 Book Now

Eagles Nest At Loon Lake Near Gore Mountain

7129 U.S. 9, Chestertown, United States Show map

Staying at the 7-bedroom Eagles Nest At Loon Lake Near Gore Mountain Chestertown villa, guests can easily reach Rustic Charm Gift Shop, located around 7 km away. With a maximum capacity of 22 guests,… More

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4 Mi To Beach & Lake: Spacious Home In Chestertown

189 Stock Farm Rd, Chestertown, United States Show map

The 4-bedroom 4 Mi To Beach & Lake: Spacious Home In Chestertown is located about 10 minutes' drive from Dynamite Hill Recreation Area, giving access to various tourist spots nearby. With a maximum… More

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The Stock Farm

528 Stock Farm Rd, Chestertown, United States Show map

The Stock Farm Villa Chestertown is located about a 10-minute drive from Rustic Charm Gift Shop and provides snow skiing, hiking, and cycling for active guests. This Chestertown holiday home boasts a… More

From US$ 402 Book Now

Sagevick Cabin

Chestertown, United States Show map

Nestled about 7 km from Rustic Charm Gift Shop, the 1-bedroom Sagevick Cabin Chestertown is boasting a picnic area and a golf course for guests' enjoyment. Located 15 minutes' drive from Loon Lake… More

From US$ 197 Book Now

Hudson Riverside Cottage

47 East Hudson River Dr, Chestertown, United States Show map

During the stay at Hudson Riverside Cottage Chestertown, guests can indulge in snow skiing, hiking, and cycling or visit Loon Lake, located 3.8 km away. Offering horse riding tours, this 2-bedroom… More

From US$ 354 Book Now

Private Contemporary

Chestertown, United States Show map

The 4-bedroom Private Contemporary Villa Chestertown is located a mere 1.9 km from Loon Lake Public Beach, giving access to various tourist spots nearby. This Chestertown villa hosts up to 8 guests… More

From US$ 502 Book Now

Lakeside Vibes

Chestertown, United States Show map

Featuring horse riding tours to make your visit more entertaining, the 3-bedroom Lakeside Vibes Chestertown villa is approximately 25 minutes' walk from Loon Lake Public Beach. Guests can enjoy snow… More

From US$ 345 Book Now

Hunerburg White House

Chestertown, United States Show map

During the stay at Hunerburg White House Chestertown villa, guests can indulge in snow skiing, horseback riding, and cycling or visit Rustic Charm Gift Shop, located a 15-minute ride away. Offering… More

From US$ 263 Book Now