Photo by Julie Miller

Search Cottages in Chestertown

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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Cottages in Chestertown

Exterior
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, (24)
"Great little get away with the family and the dogs! Met both Linda and her husband. Both very friendly and accommodating "
United States
Allan G.
The price is SAR 699
SAR 1,405 total
includes taxes & fees
2 Dec - 3 Dec
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
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, (50)
"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 SAR 694
SAR 999 total
includes taxes & fees
2 Dec - 3 Dec
Beautiful cottage on quiet country road walking distance to charming North Creek
House (2 Bedrooms) | Interior
7 Mi to Glens Falls: Peaceful Retreat w/ Game Room

7 Mi to Glens Falls: Peaceful Retreat w/ Game Room

3.0 star property
Hudson Falls
The price is SAR 919
SAR 2,536 total
includes taxes & fees
2 Dec - 3 Dec
7 Mi to Glens Falls: Peaceful Retreat w/ Game Room
Exterior
Perfect Autumn Getaway!

Perfect Autumn Getaway!

Warrensburg
The price is SAR 401
SAR 885 total
includes taxes & fees
2 Dec - 3 Dec
Perfect Autumn Getaway!
Exterior
Perfect Autumn Getaway!

Perfect Autumn Getaway!

Warrensburg
The price is SAR 523
SAR 1,223 total
includes taxes & fees
15 Dec - 16 Dec
Perfect Autumn Getaway!
Property grounds
The Pine Ridge Retreat - A Cozy Great Sacandaga Cottage with Private Lake Access

The Pine Ridge Retreat - A Cozy Great Sacandaga Cottage with Private Lake Access

2.0 star property
Hadley
The price is SAR 555
SAR 782 total
includes taxes & fees
2 Dec - 3 Dec
The Pine Ridge Retreat - A Cozy Great Sacandaga Cottage with Private Lake Access
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

Fort William Henry Hotel and Conference Center

Fort William Henry Hotel and Conference Center

10/10 Excellent
"Friendly staff, wonderful food, beautiful lake views, nice amenities. "
Kelly 2-night trip
Posted 2 days ago
Fort William Henry Hotel and Conference Center

Frequently asked questions

How much do cottages in Chestertown cost?
Prices for cottages in Chestertown range between SAR 782 and SAR 2,536 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 156 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.
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.