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Chestertown hotels

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Best Chestertown hotels

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Most recommended Chestertown hotels

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Loon's Lair, A Beautiful immaculate Adirondack 2 Bedroom 3 Bathroom Suite - Chestertown - Bedroom
Loon's Lair, A Beautiful immaculate Adirondack 2 Bedroom 3 Bathroom Suite
R4 597+
R4 597+
Free Wi-Fi
Air conditioning
The Fern Lodge - Chestertown - Living room
The Fern Lodge
10 Wonderful
R12 530+
R12 530+
Parking
Free Wi-Fi
Air conditioning
Deer Crossing, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains - Chestertown - Outdoor view
Deer Crossing, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains - Chestertown - Outdoor view
Deer Crossing, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains
R3 749+
R3 749+
Free Wi-Fi
Pet-friendly
Air conditioning
Lily Pad South At Loon Lake Near Gore Mountain - Chestertown - Bedroom
Lily Pad South At Loon Lake Near Gore Mountain - Chestertown - Bedroom
Lily Pad South At Loon Lake Near Gore Mountain
R2 770+
R2 770+
Air conditioning
Lakeside Vibes - Chestertown - Bedroom
Lakeside Vibes - Chestertown - Bedroom
Lakeside Vibes
8.5 Very Good
R9 779+
R9 779+
Free Wi-Fi
Bass Bunk, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains - Chestertown - Bedroom
Bass Bunk, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains - Chestertown - Bedroom
Bass Bunk, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains
R6 010+
R6 010+
Free Wi-Fi
Air conditioning
#7 Adirondack@Birchwood Cottages on Loon Lake. Family Friendly Waterfront - Chestertown - Outdoor view
#7 Adirondack@Birchwood Cottages on Loon Lake. Family Friendly Waterfront - Chestertown - Outdoor view
#7 Adirondack@Birchwood Cottages on Loon Lake. Family Friendly Waterfront
R5 709+
R5 709+
Free Wi-Fi
Pool
Pet-friendly
Pine Tree Motel & Cabins - Chestertown - Bedroom
Pine Tree Motel & Cabins - Chestertown - Bedroom
Pine Tree Motel & Cabins
R3 147+
R3 147+
Free Wi-Fi
Pet-friendly
Air conditioning
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing - Chestertown - Living room
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing - Chestertown - Living room
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
R7 951+
R7 951+
Air conditioning
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 - Living room
Lakefront home steps away from a private, gentle sloping sandy beach & fire pit.
R17 805+
R17 805+
Free Wi-Fi
Air conditioning
NEW for 2024, 6 person hot tub. Spacious country home with large back yard. - Chestertown - Dining room
NEW for 2024, 6 person hot tub. Spacious country home with large back yard. - Chestertown - Dining room
NEW for 2024, 6 person hot tub. Spacious country home with large back yard.
R6 877+
R6 877+
Free Wi-Fi
Air conditioning
#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming! - Chestertown - Outdoor view
#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming! - Chestertown - Outdoor view
#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
R4 503+
R4 503+
Free Wi-Fi
Pet-friendly
Winter on Loon Lake, Hot tub, ski Gore, snowmobile - Chestertown - Living room
Winter on Loon Lake, Hot tub, ski Gore, snowmobile - Chestertown - Living room
Winter on Loon Lake, Hot tub, ski Gore, snowmobile
R10 532+
R10 532+
Free Wi-Fi
Air conditioning
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George - Chestertown - Bedroom
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George - Chestertown - Bedroom
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
R6 689+
R6 689+
Free Wi-Fi
Air conditioning
Tall Pines On Loon Lake - Chestertown - Balcony
Tall Pines On Loon Lake - Chestertown - Balcony
Tall Pines On Loon Lake
R7 876+
R7 876+
Free Wi-Fi
Retreat on the Pond - Chestertown
Retreat on the Pond - Chestertown
Retreat on the Pond
9.3 Wonderful
R8 441+
R8 441+
Free Wi-Fi
Pet-friendly
Air conditioning
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3+ stars

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R4 597 - R6 595R6 595 - R8 573R8 573 - R10 551R10 551 - R12 530R12 530+ per night

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Free cancellationFree breakfastFree parkingFree internet

Good to know

Low season

September

High season

June

Average price (weeknight)

R5 206

Average price (weekend night)

R6 344
Cheapest month to stay with an average 33% drop in price.
Most expensive month to stay with an average 81% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

When to book a hotel in Chestertown

Price per night / 3-star hotel. Prices are not fixed and may vary with time.
Average nightly price per month
Average nightly price

Top tips for finding Chestertown hotel deals

  • Book at least -1 days before your stay begins to get the best price for your Rutland accommodation.

FAQs when booking a hotel in Chestertown

  • How do I find a hotel in central Chestertown?

    After you launch a hotel search on KAYAK, you can refine your research by neighbourhood, which allows you to pick the central Chestertown districts. You can also do a search using the city map to choose a specific location, like Chestertown city centre

  • How can I find hotels near me?

    Take a look at our extensive hotel map to find the best hotels near you.

Where to stay in Chestertown?

Our map will help you find the perfect place to stay in Chestertown by showing you the exact location of each hotel.

Everything you need to know for your stay in Chestertown

All hotels in Chestertown

Chestertown Hotel Deals. Search and compare hotels in Chestertown. Find cheap hotel rooms in Chestertown. KAYAK searches hundreds of travel sites to help you find cheap hotels and book the room that suits you best.

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