A waterfront town with a pier, dock, and several buildings.

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Chestertown cottages

A small cabin with a red roof, surrounded by trees and a body of water.

1. 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, (59 reviews)
"Just what we wanted. Quiet, peaceful, convenient."
United States
SHARON g.
The price is AED 661
AED 950 total
includes taxes & fees
8 Nov - 9 Nov
Beautiful cottage on quiet country road walking distance to charming North Creek
A wooden deck with a view of a lake surrounded by trees.

2. 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, (31 reviews)
"Wonderful stay at a GREAT property!Couldn't ask for more!"
United States
Robert H.
The price is AED 1,091
AED 1,366 total
includes taxes & fees
14 Oct - 15 Oct
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
A small white building with a gabled roof and a porch, surrounded by trees and grass.

3. The Elms Waterfront Cottages

The Elms Waterfront Cottages
2.5 star property
Lake Luzerne
8.6 out of 10, Excellent, (20 reviews)
"The kids had fun using the rowboat and paddle boats. The staff was very friendly and helpful."
United States
Colleen
The price is AED 1,157
AED 1,284 total
includes taxes & fees
11 Oct - 12 Oct
The Elms Waterfront Cottages
A wooden deck with a grill, two red chairs, and a welcome sign.

4. Adirondack Mountains Cottage Near Gore Mountain!

Adirondack Mountains Cottage Near Gore Mountain!
Warrensburg
10.0 out of 10, Exceptional, (132 reviews)
"Absolutely perfect. Sweet little cabin with a wonderful river view. PM has thought of every thing and we thoroughly enjoyed our stay!!"
United States
Pamela L.
Adirondack Mountains Cottage Near Gore Mountain!
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

Frequently asked questions

How much do cottages in Chestertown cost?
Prices for cottages in Chestertown range between and 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 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.