Photo by Julie Miller

Search Cottages in Chestertown

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

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 SARĀ 836
SARĀ 928 total
includes taxes & fees
13 Feb - 14 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 SARĀ 2,179
SARĀ 2,418 total
includes taxes & fees
18 Feb - 19 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, (27)
"My family and friends would like to thank Tony and Kristi (the owners) for such a great vacation at their home in Chestertown. Everything on the description of the house was accurate. The house was super cozy and comfortable. It was clean and ready for us when we arrived. The owners were helpful with a few questions we had early in our stay and quick to respond. We brought our furry buddy Willow with us, and we are pretty sure she did not want to leave. There was plenty of room for her to...
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.
Don't see what you're looking for?
See all available properties in Chestertown
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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?
Youā€™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 youā€™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?
With Expediaā€™s convenient filter tool, comparing cheap cottages in Chestertown is a breeze. To view accommodations thatā€™ll make your wallet happy, fine-tune your search results by star rating, amenities and budget.