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
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 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 ฿4,648
฿15,019 total
includes taxes & fees
19 Jul - 20 Jul
9 Mi to Lake George Village: Home in Queensbury
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 ฿12,461
฿13,831 total
includes taxes & fees
23 Jun - 24 Jun
The Elms Waterfront Cottages
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

Country Inn & Suites by Radisson, Lake George (Queensbury), NY

Country Inn & Suites by Radisson, Lake George (Queensbury), NY

10/10 Excellent
"The staff were real human beings."
Keith 1-night trip
Posted 2 hours ago
Country Inn & Suites by Radisson, Lake George (Queensbury), NY

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
Accommodation
103 Cottages
Lowest Price
฿13,831
Highest Price
฿33,796

Frequently asked questions

How much do cottages in Chestertown cost?
Prices for cottages in Chestertown range between ฿13,831 and ฿33,796 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 103 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.