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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
C$ 351+
C$ 351+
Free Wi-Fi
The Fern Lodge - Chestertown - Living room
The Fern Lodge
10 Wonderful
C$ 956+
C$ 956+
Parking
Free Wi-Fi
Friends Lake Inn - Chestertown - Restaurant
Friends Lake Inn - Chestertown - Restaurant
Friends Lake Inn
8.7 Very good
C$ 419+
C$ 419+
Parking
Free Wi-Fi
The Lodge at Loon Lake - Chestertown - Patio
The Lodge at Loon Lake - Chestertown - Patio
The Lodge at Loon Lake
8.6 Very good
C$ 303+
C$ 303+
Parking
Free Wi-Fi
Deer Crossing, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains - Chestertown - Outdoors view
Deer Crossing, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains - Chestertown - Outdoors view
Deer Crossing, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains
C$ 286+
C$ 286+
Free Wi-Fi
Pet friendly
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
C$ 211+
C$ 211+
Lakeside Vibes - Chestertown - Bedroom
Lakeside Vibes - Chestertown - Bedroom
Lakeside Vibes
8.5 Very good
C$ 746+
C$ 746+
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
C$ 458+
C$ 458+
Free Wi-Fi
#7 Adirondack@Birchwood Cottages on Loon Lake. Family Friendly Waterfront - Chestertown - Outdoors view
#7 Adirondack@Birchwood Cottages on Loon Lake. Family Friendly Waterfront - Chestertown - Outdoors view
#7 Adirondack@Birchwood Cottages on Loon Lake. Family Friendly Waterfront
C$ 435+
C$ 435+
Free Wi-Fi
Pool
Pet friendly
Pine Tree Motel & Cabins - Chestertown - Bedroom
Pine Tree Motel & Cabins - Chestertown - Bedroom
Pine Tree Motel & Cabins
C$ 240+
C$ 240+
Free Wi-Fi
Pet friendly
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.
C$ 1,358+
C$ 1,358+
Free Wi-Fi
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.
C$ 525+
C$ 525+
Free Wi-Fi
#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming! - Chestertown - Outdoors view
#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming! - Chestertown - Outdoors view
#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
C$ 343+
C$ 343+
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
C$ 803+
C$ 803+
Free Wi-Fi
Spa
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
C$ 510+
C$ 510+
Free Wi-Fi
Retreat on the Pond - Chestertown
Retreat on the Pond - Chestertown
Retreat on the Pond
9.3 Wonderful
C$ 451+
C$ 451+
Free Wi-Fi
Pet friendly
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C$ 351 - C$ 503C$ 503 - C$ 654C$ 654 - C$ 805C$ 805 - C$ 956C$ 956+ per night

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Free cancellationFree breakfastFree parkingFree internet

Good to know

Low season

September

High season

June

Average price (weeknight)

C$ 397

Average price (weekend night)

C$ 484
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.
  • How long should you stay? KAYAK users usually book their accommodation in Rutland for 2 days.

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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