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 NZ$782
includes taxes & fees
22 June - 23 June
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 NZ$419
includes taxes & fees
17 June - 18 June
Beautiful cottage on quiet country road walking distance to charming North Creek
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 NZ$887
includes taxes & fees
17 June - 18 June
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
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 NZ$719
includes taxes & fees
17 June - 18 June
The Elms Waterfront Cottages
Exterior

Convenient location for adventures in the Adirondacks!

Convenient location for adventures in the Adirondacks!
Warrensburg
The price is NZ$608
includes taxes & fees
17 June - 18 June
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 NZ$1,758
includes taxes & fees
6 July - 7 July
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

La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George

10/10 Excellent
"Great place to stay!"
Heather 2-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Lake George

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
79
Accommodation
171 Cottages
Lowest Price
NZ$419
Highest Price
NZ$1,758

Frequently asked questions

How much do cottages in Chestertown cost?
Prices for cottages in Chestertown range between NZ$419 and NZ$1,758 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 171 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.
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.