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Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

Compare Cottages in Chestertown with updated reviews, rates, and availability.

Friends Lake Inn
Property entrance

Friends Lake Inn

4.0 star property
8.8 out of 10, Excellent, (86)
"Quiet lodging and friendly staff"
The price is AED 819
AED 909 total
includes taxes & fees
2 Feb - 3 Feb
Friends Lake Inn
The Fern Lodge
Room

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (45)
"We had such a great experience the first night so we moved our plans and stayed a second, next time we will definitely stay even longer."
The price is AED 2,156
AED 2,393 total
includes taxes & fees
4 Feb - 5 Feb
The Fern Lodge
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Living area

Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing

10.0 out of 10, Exceptional, (26)
"The house was beautiful with spacious living and dining areas. The 3 season screen room was nice, though we stayed in January and didn’t get to enjoy it. The kids and husband enjoyed the foosball table and arcade game. The master bed room is in the basement and the kids room downstairs, but there is an alarm/chime in place that goes off when any door opens which put my mind at ease being on another floor. Other reviews said the basement is cold but I did not find that to be true. There are local...
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
1970s acreage surrounded by trees with deck, grill, & internet

1970s acreage surrounded by trees with deck, grill, & internet

8.0 out of 10, Very Good, (2)
"Our family booked a 2-night stay for a ski trip for President's Weekend. What mattered to us the most was cleanliness and comfort of a home as we were looking to cook dinners in the property (i.e., we were focused on a property with a full kitchen, grill, woodstove, etc.). 1. The property was generally clean and charming ("rustic", as advertised!) and we were impressed upon entering. Check-in was very easy. 4-5 star experience! 2. Unfortunately the charm wore off quickly as we noticed a...
1970s acreage surrounded by trees with deck, grill, & internet
Pine Tree Motel & Cabins
Exterior

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (126)
"very friendly and helpful owners. rooms were very clean and comfortable. good location as well"
Pine Tree Motel & Cabins
The Loft at The Remington
Exterior

The Loft at The Remington

3.5 star property
The Loft at The Remington
Stock Farm, an Adirondack Gem
Interior

Stock Farm, an Adirondack Gem

Stock Farm, an Adirondack Gem
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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Other property types in Chestertown

Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain

10.0 out of 10, Exceptional, (106)
"A fantastic location for those looking to get away in the Adirondacks. Conveniently close to Chestertown, as well as many outdoor activities, Eagles Nest was an awesome location to stay at with friends and family. "
Eagles Nest at Loon Lake near Gore Mountain
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Great Room

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

10.0 out of 10, Exceptional, (57)
"Incredible place and stay, highly recommended!"
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Lakefront cabin with beautiful loft, game room, views, private dock

Lakefront cabin with beautiful loft, game room, views, private dock

9.2 out of 10, Wonderful, (35)
"Loved everything from the coffee maker to the views at this place. Fantastic!"
Lakefront cabin with beautiful loft, game room, views, private dock
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.

Frequently asked questions

How much do cottages in Chestertown cost?
You’ll pay between and per night for cottages in Chestertown. No matter your budget, an awesome stay is just a click or two away on Expedia. 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?
Pack your bags and choose from cottages in Chestertown. Dreaming of a place where you can get reacquainted with nature? Expedia will help you find the ideal stay in a few simple clicks.
Why book your cottage in Chestertown with Expedia?
We think that traveling should be hassle-free, so if you’re after cottages in Chestertown at a competitive rate, Expedia has you covered. Stick to the budget and pick a thrifty option far away from the city rush, or splurge on a 5-star cottage to spoil the ones you love most.
How can I find cheap cottages in Chestertown?
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