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

Search Chestertown Cottage Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Chestertown cottages

A wooden deck with a grill, two red chairs, and a welcome sign.

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 ￥25,295
￥64,808 total
includes taxes & fees
Sep 17 - Sep 18
Adirondack Mountains Cottage Near Gore Mountain!
A wooden deck with a grill, two red chairs, and a welcome sign.

2. Adirondack Mountains Cottage Near Gore Mountain!

Adirondack Mountains Cottage Near Gore Mountain!
3.0 star property
Warrensburg
The price is ￥32,773
￥63,382 total
includes taxes & fees
Sep 17 - Sep 18
Adirondack Mountains Cottage Near Gore Mountain!
A small cabin with a red roof, surrounded by trees and a body of water.

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.
The price is ￥33,409
￥47,503 total
includes taxes & fees
Aug 30 - Aug 31
Beautiful cottage on quiet country road walking distance to charming North Creek
A two-story house with a sloped roof, a large tree in front, and a gravel driveway.

4. Convenient location for adventures in the Adirondacks!

Convenient location for adventures in the Adirondacks!
Warrensburg
The price is ￥28,092
￥60,255 total
includes taxes & fees
Sep 2 - Sep 3
Convenient location for adventures in the Adirondacks!
A small white building with a gabled roof and a porch, surrounded by trees and grass.

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 ￥50,113
￥55,625 total
includes taxes & fees
Sep 23 - Sep 24
The Elms Waterfront Cottages
A small, single-story cabin with a stone chimney, white siding, and multiple windows.

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, (178 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 ￥28,656
￥35,873 total
includes taxes & fees
Sep 20 - Sep 21
Walk to Million Dollar Beach from this awesome Cottage!
A wooden deck with a view of a lake surrounded by trees.

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 ￥71,449
￥90,087 total
includes taxes & fees
Aug 29 - Aug 30
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

The Queensbury Hotel

The Queensbury Hotel

10/10 Excellent
"Great experience, will stay again."
lenny 1-night trip
Posted 6 hours ago
The Queensbury Hotel

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
413
Accommodation
215 Cottages
Lowest Price
￥35,873
Highest Price
￥90,087

Frequently asked questions

How much do cottages in Chestertown cost?
Prices for cottages in Chestertown range between ￥35,873 and ￥90,087 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.