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

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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.
$367 nightly
The price is $407
Sep 10 - Sep 11
Total with taxes and fees
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
$359 nightly
The price is $398
Sep 10 - Sep 11
Total with taxes and fees
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, (58 reviews)
"Just what we wanted. Quiet, peaceful, convenient."
United States
SHARON g.
$269 nightly
The price is $299
Sep 10 - Sep 11
Total with taxes and fees
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
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.
$361 nightly
The price is $366
Sep 29 - Sep 30
Total with taxes and fees
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
$315 nightly
The price is $350
Sep 13 - Sep 14
Total with taxes and fees
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, (179 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
$206 nightly
The price is $229
Sep 20 - Sep 21
Total with taxes and fees
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

Comfort Inn & Suites Lake George

Comfort Inn & Suites Lake George

10/10 Excellent
"N/A"
Leonel Andrés 2-night trip
Posted 1 hour ago
Comfort Inn & Suites Lake George

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
368
Accommodation
204 Cottages
Lowest Price
$229
Highest Price
$407

Frequently asked questions

How much do cottages in Chestertown cost?
Prices for cottages in Chestertown range between $229 and $407 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 204 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.
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 cozy 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 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.
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.