Photo by Julie Miller

Search Cottages in Chestertown

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Check prices for these dates

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21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov
In one month
12 Dec - 14 Dec
In two months
9 Jan - 11 Jan

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, (23)
"This is a beautiful property on an idyllic lake which we enjoyed very much. Linda was a more than accommodating host and we enjoyed talking with her and learning about the property and the area. Great water activities, especially the paddle boarding and canoeing. Proximity to Lake George is a plus!"
United States
Lois S.
The price is AED 731
AED 1,431 total
includes taxes & fees
17 Nov - 18 Nov
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)
"Cute cottage well stocked. Loved being on the Hudson with a nice small private access point to it. Would come stay again. "
United States
chris p.
The price is AED 533
AED 795 total
includes taxes & fees
17 Nov - 18 Nov
Beautiful cottage on quiet country road walking distance to charming North Creek
Exterior
Perfect Autumn Getaway!

Perfect Autumn Getaway!

Warrensburg
The price is AED 393
AED 862 total
includes taxes & fees
17 Nov - 18 Nov
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 AED 544
AED 766 total
includes taxes & fees
14 Dec - 15 Dec
The Pine Ridge Retreat - A Cozy Great Sacandaga Cottage with Private Lake Access
Exterior
Perfect Autumn Getaway!

Perfect Autumn Getaway!

Warrensburg
The price is AED 524
AED 1,205 total
includes taxes & fees
14 Dec - 15 Dec
Perfect Autumn Getaway!
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
"Everything good - a continental breakfast would be nice - maybe just real milk for coffee & pastries & oatmeal? "
carolann 1-night trip
Posted 3 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 AED 766 and AED 1,431 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.

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