Search Chestertown Cottage Rentals from CA $585

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Chestertown cottages

Exterior

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, (54 reviews)
"It was a nice place, comfortable, nice location. Could have been cleaner but we had a nice relaxing time. "
United States
Mary M.
The price is CA $237
CA $339 total
includes taxes & fees
Jun 14 - Jun 15
Beautiful cottage on quiet country road walking distance to charming North Creek
Exterior

Convenient location for adventures in the Adirondacks!

Convenient location for adventures in the Adirondacks!
Warrensburg
The price is CA $228
CA $500 total
includes taxes & fees
Jun 9 - Jun 10
Convenient location for adventures in the Adirondacks!
Exterior

The Elms Waterfront Cottages

The Elms Waterfront Cottages
2.5 star property
Lake Luzerne
8.4 out of 10, Very good, (16 reviews)
"We were treated like royalty here at the Elms. The owner, Chandler and his staff, go above and beyond. What a beautiful escape. We will most definitely return. "
United States
Amanda
The price is CA $527
CA $585 total
includes taxes & fees
Jun 8 - Jun 9
The Elms Waterfront Cottages
Property grounds

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, (25 reviews)
"Wonderful stay at a GREAT property!Couldn't ask for more!"
United States
Robert H.
The price is CA $424
CA $732 total
includes taxes & fees
Jun 18 - Jun 19
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
House (4 Bedrooms) | Interior

Warrensburg Home ~ 6 Mi to Lake George!

Warrensburg Home ~ 6 Mi to Lake George!
3.0 star property
Warrensburg
10.0 out of 10, Exceptional, (1 review)
The price is CA $826
CA $1,429 total
includes taxes & fees
Jul 6 - Jul 7
Warrensburg Home ~ 6 Mi to Lake George!
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

The Queensbury Hotel

The Queensbury Hotel

10/10 Excellent
"Very clean and well kept. Love the historic feel. Definitely be here again in the future...."
William 1-night trip
Posted 10 hours ago
The Queensbury Hotel

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
Accommodation
174 Cottages
Lowest Price
CA $585
Highest Price
CA $1,429

Frequently asked questions

How much do cottages in Chestertown cost?
Prices for cottages in Chestertown range between CA $585 and CA $1,429 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 174 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.

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