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

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 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 £294
includes taxes & fees
25 Aug - 26 Aug
Adirondack Mountains Cottage Near Gore Mountain!
Cottage (2 Bedrooms) | Interior

2. Adirondack Mountains Cottage Near Gore Mountain!

Adirondack Mountains Cottage Near Gore Mountain!
3.0 star property
Warrensburg
The price is £292
includes taxes & fees
25 Aug - 26 Aug
Adirondack Mountains Cottage Near Gore Mountain!
Exterior

3. 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, (57 reviews)
"Just what we wanted. Quiet, peaceful, convenient."
United States
SHARON g.
The price is £219
includes taxes & fees
23 Aug - 24 Aug
Beautiful cottage on quiet country road walking distance to charming North Creek
Exterior

4. Convenient location for adventures in the Adirondacks!

Convenient location for adventures in the Adirondacks!
Warrensburg
The price is £275
includes taxes & fees
16 Sept - 17 Sept
Convenient location for adventures in the Adirondacks!
Exterior

5. 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 £256
includes taxes & fees
13 Sept - 14 Sept
The Elms Waterfront Cottages
Property grounds

6. 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 £406
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

Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites

10/10 Excellent
"Parking always available, room small but clean , staff friendly, shower working properly, loved covered pool , water was warm kids loved it, tennis table available ( just bring you ping pong balls and paddles ) had one issue with a door- manager came and quickly resolved it."
Vasyl 3-night trip
Posted less than an hour ago
Adirondack Retreat Inn & Suites

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
19
Accommodation
208 Cottages
Lowest Price
£256
Highest Price
£292

Frequently asked questions

How much do cottages in Chestertown cost?
Prices for cottages in Chestertown range between £256 and £292 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 208 cottages in Chestertown. No matter if you're travelling with the little ones or planning a weekend break with close friends, Expedia can help you find the ideal property to reconnect with nature.
Are there any family-friendly cottages in Chestertown?
If you're looking to get in touch with nature in Chestertown, you can't go past Sunset Mountain Lodge. With a 3-star rating and amenities like a playground and a picnic area, you'll feel right at home at this family-friendly cottage. Chestertown boasts an array of family-friendly attractions to explore when you need to keep the kids busy. Natural Stone Bridge and Caves and Loon Lake Beach promise a fun day out for visitors of all ages.
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 holiday 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.
What is there to do in Chestertown near my cottage?
If you want to make the most of your time in Chestertown, make your way to Loon Lake Beach. It's popular among visitors and locals alike.