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

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Check prices for these dates

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

Our top choices for Chestertown cottages

Outdoor dining

1. Adirondack Mountains Cottage Near Gore Mountain!

Adirondack Mountains Cottage Near Gore Mountain!
Warrensburg
9.8 out of 10, Exceptional, (129 reviews)
"Easy to get to yet very serene. Anything you want or need was provided in the cabin. "
United States
Roy M.
The price is €355
includes taxes & fees
4 Sept - 5 Sept
Adirondack Mountains Cottage Near Gore Mountain!
Exterior

2. 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 €263
includes taxes & fees
17 Aug - 18 Aug
Beautiful cottage on quiet country road walking distance to charming North Creek
Cottage (2 Bedrooms) | Interior

3. Adirondack Mountains Cottage Near Gore Mountain!

Adirondack Mountains Cottage Near Gore Mountain!
3.0 star property
Warrensburg
The price is €346
includes taxes & fees
4 Sept - 5 Sept
Adirondack Mountains Cottage Near Gore Mountain!
Exterior

4. Convenient location for adventures in the Adirondacks!

Convenient location for adventures in the Adirondacks!
Warrensburg
The price is €351
includes taxes & fees
1 Sept - 2 Sept
Convenient location for adventures in the Adirondacks!
Exterior

5. 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 €363
includes taxes & fees
13 Aug - 14 Aug
The Elms Waterfront Cottages
Property grounds

6. 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 €607
includes taxes & fees
21 Aug - 22 Aug
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

Scotty's Lakeside Resort

Scotty's Lakeside Resort

10/10 Excellent
"There isn't one bad thing I can say about this hotel. It's only a five-minute drive to the main shopping center, or you can enjoy a nice walk there if you prefer. The hotel has everything you need, including a heated pool, a lake, plenty of lounge chairs, and on-site kayak and paddle boat rentals. There is also a small arcade. While it's a fun idea, it's quite old, runs on quarters, and some of the machines occasionally keep your coins, so I wouldn't recommend spending much time there. This hotel is definitely family-friendly and offers plenty of activities to keep kids entertained. They also have food available on-site, which is very convenient. Overall, I would absolutely recommend this hotel to anyone looking for a fun, relaxing, and family-friendly place to stay."
Joseph 3-night trip
Posted 3 hours ago
Scotty's Lakeside Resort

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
230
Accommodation
215 Cottages
Lowest Price
€263
Highest Price
€607

Frequently asked questions

How much do cottages in Chestertown cost?
Prices for cottages in Chestertown range between €263 and €607 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 215 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.