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

Book a Chestertown Cottage

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chestertown cottages

1. Adirondack Mountains Cottage Near Gore Mountain!

Adirondack Mountains Cottage Near Gore Mountain!
Warrensburg
9.8 out of 10, Exceptional, (130 reviews)
"We had a great stay here. The view was incredible and we really enjoyed exploring the area- would definitely recommend "
United Kingdom
Jennie M.
The price is NZ$710
includes taxes & fees
25 Sept - 26 Sept
Adirondack Mountains Cottage Near Gore Mountain!

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, (58 reviews)
"Just what we wanted. Quiet, peaceful, convenient."
United States
SHARON g.
The price is NZ$516
includes taxes & fees
22 Sept - 23 Sept
Beautiful cottage on quiet country road walking distance to charming North Creek

3. Adirondack Mountains Cottage Near Gore Mountain!

Adirondack Mountains Cottage Near Gore Mountain!
3.0 star property
Warrensburg
The price is NZ$696
includes taxes & fees
25 Sept - 26 Sept
Adirondack Mountains Cottage Near Gore Mountain!

4. Convenient location for adventures in the Adirondacks!

Convenient location for adventures in the Adirondacks!
Warrensburg
8.0 out of 10, Very good, (1 review)
"Satisfied with the stay. Host was very responsive. The house itself isn’t as big as it appears in pictures, but enjoyed my stay regardless."
United States
Chris A.
The price is NZ$627
includes taxes & fees
23 Sept - 24 Sept
Convenient location for adventures in the Adirondacks!

5. 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 NZ$611
includes taxes & fees
22 Sept - 23 Sept
The Elms Waterfront Cottages

6. Walk to Million Dollar Beach from this awesome Cottage!

Walk to Million Dollar Beach from this awesome Cottage!
Lake George
10.0 out of 10, Exceptional, (181 reviews)
"Great communication from the owner throughout. The home was in beautiful condition and just as advertised. Very comfortable and cozy, and the location in relation to activities was perfect. We would definitely recommend this home and will look to rebook again in 2027"
United States
Sean
Walk to Million Dollar Beach from this awesome Cottage!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chestertown Hotel Reviews

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
Accommodation
208 Cottages
Lowest Price
NZ$611
Highest Price
NZ$696

Frequently asked questions

How much do cottages in Chestertown cost?
Prices for cottages in Chestertown range between NZ$611 and NZ$696 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 208 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.