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

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Chestertown cottages

Outdoor dining

1. Adirondack Mountains Cottage Near Gore Mountain!

Adirondack Mountains Cottage Near Gore Mountain!
Warrensburg
9.8 out of 10, Exceptional, (130 reviews)
"Easy to get to yet very serene. Anything you want or need was provided in the cabin. "
United States
Roy M.
The price is AED 584
AED 1,496 total
includes taxes & fees
25 Aug - 26 Aug
Adirondack Mountains Cottage Near Gore Mountain!
Exterior

2. Beautiful cottage on quiet country road walking distance to charming North Creek

Beautiful cottage on quiet country road walking distance to charming North Creek
North Creek
9.8 out of 10, Exceptional, (58 reviews)
"Just what we wanted. Quiet, peaceful, convenient."
United States
SHARON g.
The price is AED 771
AED 1,097 total
includes taxes & fees
25 Aug - 26 Aug
Beautiful cottage on quiet country road walking distance to charming North Creek
Cottage (2 Bedrooms) | Interior

3. Adirondack Mountains Cottage Near Gore Mountain!

Adirondack Mountains Cottage Near Gore Mountain!
3.0 star property
Warrensburg
The price is AED 757
AED 1,463 total
includes taxes & fees
25 Aug - 26 Aug
Adirondack Mountains Cottage Near Gore Mountain!
Exterior

4. Convenient location for adventures in the Adirondacks!

Convenient location for adventures in the Adirondacks!
Warrensburg
The price is AED 649
AED 1,391 total
includes taxes & fees
23 Sep - 24 Sep
Convenient location for adventures in the Adirondacks!
Exterior

5. Walk to Million Dollar Beach from this awesome Cottage!

Walk to Million Dollar Beach from this awesome Cottage!
Lake George
10.0 out of 10, Exceptional, (177 reviews)
"The cottage was wonderful— cozy, impeccably clean, and well located. Loved our stay, and communication with the owner was seamless. "
United States
Donna M.
The price is AED 661
AED 828 total
includes taxes & fees
20 Sep - 21 Sep
Walk to Million Dollar Beach from this awesome Cottage!
Exterior

6. The Elms Waterfront Cottages

The Elms Waterfront Cottages
2.5 star property
Lake Luzerne
8.6 out of 10, Excellent, (19 reviews)
"The kids had fun using the rowboat and paddle boats. The staff was very friendly and helpful."
United States
Colleen
The price is AED 1,157
AED 1,284 total
includes taxes & fees
13 Sep - 14 Sep
The Elms Waterfront Cottages
Property grounds

7. Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
Fort Ann
10.0 out of 10, Exceptional, (28 reviews)
"Wonderful stay at a GREAT property!Couldn't ask for more!"
United States
Robert H.
The price is AED 1,648
AED 2,078 total
includes taxes & fees
29 Aug - 30 Aug
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
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

The Queensbury Hotel

The Queensbury Hotel

8/10 Good
"Room and hotel was very clean and well maintained. Staff at front desk and in hotel were friendly and helpful. Close to small town and easy to walk around."
Dennis 3-night trip
Posted 1 hour ago
The Queensbury Hotel

Frequently asked questions

How much do cottages in Chestertown cost?
Prices for cottages in Chestertown range between AED 828 and AED 2,078 per night. Whatever your budget, you're sure to find the perfect place to immerse yourself in nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Chestertown?
You can choose from 210 cottages in Chestertown. No matter if you're traveling with the little ones or planning a weekend break with close friends, Expedia can help you find the ideal property to reconnect with nature.
Why book your cottage in Chestertown with Expedia?
Booking a cottage in Chestertown is as simple as entering your travel dates and picking your ideal place for a vacation in the outdoors. From chic retreats to budget-friendly stays and cottages that have perks like free WiFi, Expedia has something for all tastes. As for terrific deals? We've got them as well!
How can I find cheap cottages in Chestertown?
The easiest way to score cheap cottages in Chestertown is with Expedia's handy filter tool. Tailor your search results by amenities, budget and star rating to secure unbeatable prices in just a few keystrokes.