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

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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)
"We had a great stay here. The view was incredible and we really enjoyed exploring the area- would definitely recommend "
United Kingdom
Jennie M.
The price is €350
includes taxes & fees
25 Sept - 26 Sept
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 €266
includes taxes & fees
22 Sept - 23 Sept
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 €347
includes taxes & fees
25 Sept - 26 Sept
Adirondack Mountains Cottage Near Gore Mountain!
Exterior

4. Convenient location for adventures in the Adirondacks!

Convenient location for adventures in the Adirondacks!
Warrensburg
8.0 out of 10, Very good, (1 review)
"Satisfied with the stay. Host was very responsive. The house itself isn’t as big as it appears in pictures, but enjoyed my stay regardless."
United States
Chris A.
The price is €311
includes taxes & fees
23 Sept - 24 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, (20 reviews)
"The kids had fun using the rowboat and paddle boats. The staff was very friendly and helpful."
United States
Colleen
The price is €304
includes taxes & fees
22 Sept - 23 Sept
The Elms Waterfront Cottages
Exterior

6. 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, (181 reviews)
"Great communication from the owner throughout. The home was in beautiful condition and just as advertised. Very comfortable and cozy, and the location in relation to activities was perfect. We would definitely recommend this home and will look to rebook again in 2027"
United States
Sean
Walk to Million Dollar Beach from this awesome Cottage!
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

Lakefront Terrace Resort

Lakefront Terrace Resort

8/10 Good
"Clean room, nice view but a little far of shepard park, 18-20 minutes walk"
Cesar 2-night trip
Posted less than an hour ago
Lakefront Terrace Resort

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
Accommodation
202 Cottages
Lowest Price
€304
Highest Price
€347

Frequently asked questions

How much do cottages in Chestertown cost?
Prices for cottages in Chestertown range between €304 and €347 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 202 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 want to slow the pace down a notch in Chestertown, make a booking for the crew at Sunset Mountain Lodge. With a 3-star rating and conveniences like a playground and WiFi, you'll have no trouble settling in at this family-friendly cottage. After checking in and kicking back together in your cosy digs, it's time to head out and discover the local sights. Natural Stone Bridge and Caves and Loon Lake Beach are top family-friendly attractions in Chestertown.
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.