Chestertown hotels

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Best Chestertown hotels

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R3 644 - R4 893R4 893 - R6 142R6 142 - R7 390R7 390 - R8 639R8 639+ per night

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Most recommended Chestertown hotels

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The Lodge at Loon Lake - Chestertown - Patio
The Lodge at Loon Lake
Chestertown, NY, United States
9.1Wonderful(196)
Parking
Free Wi-Fi
Air conditioning
R3 931+
Check availability
The Fern Lodge - Chestertown - Living room
The Fern Lodge
Chestertown, NY, United States
10Wonderful(19)
Parking
Free Wi-Fi
Air conditioning
R9 297+
Check availability
Friends Lake Inn - Chestertown
Friends Lake Inn
Chestertown, NY, United States
8.0Very Good(91)
Air conditioning
R4 640+
Check availability
Adirondack home, near Gore Mt ski resort, North Creek, and Loon lake. - Chestertown - Bedroom
Adirondack home, near Gore Mt ski resort, North Creek, and Loon lake.
Chestertown, NY, United States
9.7Wonderful(15)
House
Air conditioning
R8 554+
Check availability
Beautiful waterfront home with hot tub & firepit - right on the river's edge - Chestertown - Living room
Beautiful waterfront home with hot tub & firepit - right on the river's edge
Chestertown, NY, United States
8.7Very Good(11)
House
Free Wi-Fi
R11 338+
Check availability
Lakefront home steps away from a private, gentle sloping sandy beach & fire pit. - Chestertown - Living room
Lakefront home steps away from a private, gentle sloping sandy beach & fire pit.
Chestertown, NY, United States
9.9Wonderful(25)
House
Free Wi-Fi
Air conditioning
R15 944+
Check availability
Lakefront Cabin With Beautiful Loft, Game Room, Views, Private Dock - Chestertown - Bedroom
Lakefront Cabin With Beautiful Loft, Game Room, Views, Private Dock
Chestertown, NY, United States
9.1Wonderful(29)
House
R12 789+
Check availability
Lakefront cabin with beautiful views, lake and beach access - Chestertown - Living room
Lakefront cabin with beautiful views, lake and beach access
Chestertown, NY, United States
9.5Wonderful(12)
House
R3 071+
Check availability
Pine Tree Motel & Cabins - Chestertown - Bedroom
Pine Tree Motel & Cabins
Chestertown, NY, United States
Free Wi-Fi
Air conditioning
R3 273+
Check availability
Private Adirondack lakefront Cottage on Loon Lake - Chestertown - Dining room
Private Adirondack lakefront Cottage on Loon Lake
Chestertown, NY, United States
9.6Wonderful(5)
Cottage
Free Wi-Fi
R5 382+
Check availability
Cozy Adirondack condo in quaint Chestertown, near Lake George & Gore Mountain - Chestertown - Living room
Cozy Adirondack condo in quaint Chestertown, near Lake George & Gore Mountain
Chestertown, NY, United States
9.6Wonderful(5)
Condo
Free Wi-Fi
Air conditioning
R4 370+
Check availability
Cozy Adirondack Jem Your Four Season Getaway - Chestertown - Bedroom
Cozy Adirondack Jem Your Four Season Getaway
Chestertown, NY, United States
10Wonderful(6)
Apartment
Parking
Free Wi-Fi
Air conditioning
R4 134+
Check availability
Lakefront spacious contemporary. Large families welcome. Ski GORE nearby! - Chestertown - Living room
Lakefront spacious contemporary. Large families welcome. Ski GORE nearby!
Chestertown, NY, United States
9.7Wonderful(28)
House
Free Wi-Fi
R10 427+
Check availability
Dog-friendly cabin with lakefront location, 20' dock, smart TV - Chestertown - Dining room
Dog-friendly cabin with lakefront location, 20' dock, smart TV
Chestertown, NY, United States
7.3Good(16)
House
R7 829+
Check availability
Rustic Adirondacks Home with Hot Tub and Lake Access! - Chestertown
Rustic Adirondacks Home with Hot Tub and Lake Access!
Chestertown, NY, United States
9.7Wonderful(18)
House
Free Wi-Fi
Pet-friendly
Air conditioning
R7 205+
Check availability
Riverside Bliss - Chestertown
Riverside Bliss
Chestertown, NY, United States
9.7Wonderful(2)
House
R12 722+
Check availability

Popular filters in Chestertown hotels

Hotels with parking
The Lodge at Loon Lake, The Fern Lodge and others
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

July
September
R4 486
R2 726
Cheapest month to stay with an average 55% drop in price.
Most expensive month to stay with an average 45% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

FAQs when booking a hotel in Chestertown

  • How do I find a hotel in central Chestertown?

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Where to stay in Chestertown?

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Everything you need to know for your stay in Chestertown

All hotels in Chestertown