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

Search Chestertown Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

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, (129 reviews)
"Easy to get to yet very serene. Anything you want or need was provided in the cabin. "
United States
Roy M.
$367 nightly
The price is $407
Sep 4 - Sep 5
Total with taxes and fees
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, (56 reviews)
"Just what we wanted. Quiet, peaceful, convenient."
United States
SHARON g.
$269 nightly
The price is $299
Aug 16 - Aug 17
Total with taxes and fees
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
$359 nightly
The price is $398
Sep 4 - Sep 5
Total with taxes and fees
Adirondack Mountains Cottage Near Gore Mountain!
Exterior

4. Convenient location for adventures in the Adirondacks!

Convenient location for adventures in the Adirondacks!
Warrensburg
$380 nightly
The price is $385
Sep 8 - Sep 9
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, (19 reviews)
"The kids had fun using the rowboat and paddle boats. The staff was very friendly and helpful."
United States
Colleen
$378 nightly
The price is $420
Aug 13 - Aug 14
Total with taxes and fees
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, (27 reviews)
"Wonderful stay at a GREAT property!Couldn't ask for more!"
United States
Robert H.
$507 nightly
The price is $562
Aug 21 - Aug 22
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
231
Accommodation
215 Cottages
Lowest Price
$299
Highest Price
$562

Frequently asked questions

How much do cottages in Chestertown cost?
Prices for cottages in Chestertown range between $299 and $562 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 215 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.

Explore a world of travel with Expedia