Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Chestertown cottages

House (3 Bedrooms) | Interior

9 Mi to Lake George Village: Home in Queensbury

9 Mi to Lake George Village: Home in Queensbury
3.0 star property
Queensbury
The price is €397
includes taxes & fees
19 Jul - 20 Jul
9 Mi to Lake George Village: Home in Queensbury
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 €216
includes taxes & fees
21 Jun - 22 Jun
Beautiful cottage on quiet country road walking distance to charming North Creek
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 €366
includes taxes & fees
23 Jun - 24 Jun
The Elms Waterfront Cottages
Exterior

Convenient location for adventures in the Adirondacks!

Convenient location for adventures in the Adirondacks!
Warrensburg
The price is €395
includes taxes & fees
8 Jul - 9 Jul
Convenient location for adventures in the Adirondacks!
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 €894
includes taxes & fees
6 Jul - 7 Jul
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
"Old world class and comfort in Glens Falls. We had a wonderful stay and will definitely return"
Todd 2-night trip
Posted 3 hours ago
The Queensbury Hotel

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
Accommodation
166 Cottages
Lowest Price
€366
Highest Price
€894

Frequently asked questions

How much do cottages in Chestertown cost?
Prices for cottages in Chestertown range between €366 and €894 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 166 cottages in Chestertown. No matter if you're travelling 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 cosy 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 holiday 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.