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

Search Chestertown Cottage Rentals from CA $419

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Chestertown cottages

Exterior

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, (56 reviews)
"Just what we wanted. Quiet, peaceful, convenient."
United States
SHARON g.
The price is CA $295
CA $419 total
includes taxes & fees
Aug 16 - Aug 17
Beautiful cottage on quiet country road walking distance to charming North Creek
Exterior

2. Convenient location for adventures in the Adirondacks!

Convenient location for adventures in the Adirondacks!
Warrensburg
The price is CA $274
CA $549 total
includes taxes & fees
Sep 2 - Sep 3
Convenient location for adventures in the Adirondacks!
Exterior

3. The Elms Waterfront Cottages

The Elms Waterfront Cottages
2.5 star property
Lake Luzerne
8.6 out of 10, Excellent, (18 reviews)
"The kids had fun using the rowboat and paddle boats. The staff was very friendly and helpful."
United States
Colleen
The price is CA $531
CA $589 total
includes taxes & fees
Aug 5 - Aug 6
The Elms Waterfront Cottages
Property grounds

4. 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, (27 reviews)
"Wonderful stay at a GREAT property!Couldn't ask for more!"
United States
Robert H.
The price is CA $623
CA $986 total
includes taxes & fees
Aug 21 - Aug 22
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
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
"A high quality property. Maintained very well and obviously upgraded. Enjoyed the restaurant. Steak au poivre was delish, as was the Crabcake and Cheeseburger. Pool and hot tub are inviting too."
Bruce 2-night trip
Posted less than an hour ago
The Queensbury Hotel

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
101
Accommodation
210 Cottages
Lowest Price
CA $419
Highest Price
CA $1,088

Frequently asked questions

How much do cottages in Chestertown cost?
Prices for cottages in Chestertown range between CA $419 and CA $1,088 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 210 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.
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 cozy 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 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.
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.

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