A waterfront town with a pier, dock, and several buildings.

Chestertown Castle Hotels

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Check prices for these dates

Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27
In one month
Oct 9 - Oct 11
In two months
Nov 6 - Nov 8
No exact matches found, but these alternatives could be just right

Recommended hotels in Chestertown

1. Friends Lake Inn

Friends Lake Inn
4.0 star property
Chestertown
8.8 out of 10, Excellent, (120 reviews)
"Staff were welcoming. They have good food as well."
United States
Jessica
$115 nightly
The price is $128
Sep 9 - Sep 10
Total with taxes and fees
Friends Lake Inn
A small, single-story house with a gabled roof and a front porch.

2. Pine Tree Motel & Cabins

Pine Tree Motel & Cabins
2.0 star property
Chestertown
9.2 out of 10, Wonderful, (163 reviews)
"The room was very clean, the bed was extremely comfortable, and the staff were very friendly. We had a very pleasant stay."
United States
Pingfei
$175 nightly
The price is $194
Sep 9 - Sep 10
Total with taxes and fees
Pine Tree Motel & Cabins
A two-story house with a porch, a sign indicating 'SOUTH', and a well-maintained garden with various shrubs and a small tree.

3. The Lily Pad at Loon Lake near Gore Mountain

The Lily Pad at Loon Lake near Gore Mountain
Chestertown
9.6 out of 10, Exceptional, (43 reviews)
"Perfect for what we needed as a family of 8,, the host was very easy to communicate with as well."
United States
Sara Beth E.
$391 nightly
The price is $434
Sep 9 - Sep 10
Total with taxes and fees
The Lily Pad at Loon Lake near Gore Mountain
A large, multi-story log cabin with a prominent chimney, surrounded by dense forest and rocky terrain.

4. The Fern Lodge

The Fern Lodge
3.5 star property
Chestertown
9.8 out of 10, Exceptional, (58 reviews)
"Staff is great,friendly and helpful Loved our stay. Place is beautiful"
United States
robert
$445 nightly
The price is $494
Sep 23 - Sep 24
Total with taxes and fees
The Fern Lodge
A rustic lodge with a stone facade and a red roof, surrounded by trees and a clear sky.

5. Authentic Log Cabin with Lake Views and Sauna

Authentic Log Cabin with Lake Views and Sauna
Chestertown
9.4 out of 10, Exceptional, (3 reviews)
"Very nice cabin with amenities. Thank you for a great stay."
United States
Joe F.
$309 nightly
The price is $343
Sep 9 - Sep 10
Total with taxes and fees
Authentic Log Cabin with Lake Views and Sauna
A log cabin with a snow-covered roof, surrounded by snow-laden trees.

6. Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain
Chestertown
10.0 out of 10, Exceptional, (122 reviews)
"Great house. Great location"
United States
David S.
$628 nightly
The price is $697
Sep 13 - Sep 14
Total with taxes and fees
Eagles Nest at Loon Lake near Gore Mountain
A log cabin-style building with a porch, windows, and a green roof.

7. Super 8 by Wyndham Lake George/Warrensburg Area

Super 8 by Wyndham Lake George/Warrensburg Area
2.5 star property
Lake George
8.6 out of 10, Excellent, (1,011 reviews)
"Great location. Good parking. Nice, clean, comfortable rooms. Loved that is was pet-friendly and provided 24/7 coffee & tea station."
United States
Andrew
$71 nightly
The price is $79
Sep 13 - Sep 14
Total with taxes and fees
Super 8 by Wyndham Lake George/Warrensburg Area
A two-story building with a dark exterior, a covered front porch, and a sign reading "TALPINE LODGE".

8. The Alpine Lodge

The Alpine Lodge
3.0 star property
North Creek
9.0 out of 10, Wonderful, (700 reviews)
"Hotel is quaint and cute and clean. It is in the middle of a small town off the beaten path but for an overnighter very nice"
United States
Michael
$127 nightly
The price is $141
Sep 20 - Sep 21
Total with taxes and fees
The Alpine Lodge
A wooden building with a balcony, a clock, and a lifebuoy.

9. The Juliana Resort

The Juliana Resort
2.5 star property
Diamond Point
8.8 out of 10, Excellent, (209 reviews)
"Beautiful scenery. Unfortunately it rained the whole time but we were still able to be outside and enjoy the relaxation. Would definitely stay again."
United States
Heather
$92 nightly
The price is $102
Sep 13 - Sep 14
Total with taxes and fees
The Juliana Resort
A wooden building with large windows and a metal roof.

10. Gore Mountain Lodge

Gore Mountain Lodge
2.0 star property
North Creek
9.2 out of 10, Wonderful, (219 reviews)
"There was a restaurant on the property. It was easy to check in"
United States
Henry
$149 nightly
The price is $165
Sep 27 - Sep 28
Total with taxes and fees
Gore Mountain Lodge
An aerial view of a lakeside property with a dock, a gazebo, and a large house with a porch.

11. Depe Dene Lakeside Resort

Depe Dene Lakeside Resort
2.0 star property
Lake George
9.0 out of 10, Wonderful, (521 reviews)
"Good lake access, nice accommodations, beautiful improvements made to the beach area!"
United States
Melissa
$92 nightly
The price is $102
Sep 13 - Sep 14
Total with taxes and fees
Depe Dene Lakeside Resort
A white building with a yellow-striped awning, a signboard with 'Admiral Motel' and 'VACANCY' text, and a 'WELCOME' sign.

12. Admiral Motel

Admiral Motel
2.5 star property
Lake George
9.4 out of 10, Exceptional, (809 reviews)
"Great hotel, great staff!"
United States
Grayson
$73 nightly
The price is $81
Sep 17 - Sep 18
Total with taxes and fees
Admiral Motel
A log cabin with a wooden porch and stone walls, surrounded by a well-maintained garden with various plants and flowers.

13. Lodge at Schroon Lake

Lodge at Schroon Lake
3.0 star property
Schroon Lake
9.0 out of 10, Wonderful, (545 reviews)
"Amazing stay"
United States
Michaelangelo
$174 nightly
The price is $196
Sep 14 - Sep 15
Total with taxes and fees
Lodge at Schroon Lake
A two-story white building with a porch, labeled "Maple Leaf Lodge".

14. Maple Leaf Motel

Maple Leaf Motel
2.5 star property
Schroon Lake
8.8 out of 10, Excellent, (657 reviews)
"Quaint and charming classic motel, beautiful area, totally adequate room. Would stay again!"
United States
Richard
$110 nightly
The price is $124
Sep 20 - Sep 21
Total with taxes and fees
Maple Leaf Motel
A cozy fireplace with a stone wall, a wooden shelf with books and candles, and a table with a bowl of apples and wine glasses.

15. Garnet Hill Lodge

Garnet Hill Lodge
3.0 star property
North River
9.4 out of 10, Exceptional, (211 reviews)
"Great place, Great location."
United States
Jonathan
$151 nightly
The price is $168
Sep 9 - Sep 10
Total with taxes and fees
Garnet Hill Lodge
The exterior of Georgian Lakeside Resort with a prominent illuminated sign.

16. The Georgian Lakeside Resort

The Georgian Lakeside Resort
2.5 star property
Lake George
8.8 out of 10, Excellent, (1,000 reviews)
"Amazing resort!!"
United States
cait
$106 nightly
The price is $118
Oct 4 - Oct 5
Total with taxes and fees
The Georgian Lakeside Resort
A greenhouse-style building with a glass roof, surrounded by lush greenery and a swimming pool.

17. Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites
2.5 star property
Lake George
9.2 out of 10, Wonderful, (1,013 reviews)
"easy walk to town i would stay there again"
United States
Beth ann
$79 nightly
The price is $87
Sep 15 - Sep 16
Total with taxes and fees
Adirondack Retreat Inn & Suites
A white building with a porch, an American flag, hanging flower baskets, and a sign that reads "Office."

18. Heritage of Lake George

Heritage of Lake George
3.0 star property
Lake George
9.0 out of 10, Wonderful, (778 reviews)
"The motel was really nice and clean. We will definitely go back and stay there. Great place and good location!"
United States
Shaun Marie
$87 nightly
The price is $97
Sep 27 - Sep 28
Total with taxes and fees
Heritage of Lake George
A multi-story hotel with balconies, a stone facade, and a green roof.

19. Courtyard by Marriott Lake George

Courtyard by Marriott Lake George
3.0 star property
Lake George
9.2 out of 10, Wonderful, (1,004 reviews)
"Beautiful location, will come back"
United States
Yasmeen
$148 nightly
The price is $164
Sep 23 - Sep 24
Total with taxes and fees
Courtyard by Marriott Lake George
A wooden deck with a grill, two red chairs, and a welcome sign.

20. Adirondack Mountains Cottage Near Gore Mountain!

Adirondack Mountains Cottage Near Gore Mountain!
Warrensburg
9.8 out of 10, Exceptional, (130 reviews)
"We had a great stay here. The view was incredible and we really enjoyed exploring the area- would definitely recommend "
United Kingdom
Jennie M.
$367 nightly
The price is $407
Sep 10 - Sep 11
Total with taxes and fees
Adirondack Mountains Cottage Near Gore Mountain!
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.
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Top Chestertown Hotel Reviews

Great Escape Lodge & Indoor Waterpark

Great Escape Lodge & Indoor Waterpark

10/10 Excellent
"Very fun for the family!"
Jorge 2-night trip
Posted 1 hour ago
Great Escape Lodge & Indoor Waterpark

Find out more about Chestertown

Chestertown Castles information

Number of reviews
7,328
Accommodation
7 Castles
Lowest Price
$79
Highest Price
$697

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