Photo by Julie Miller

Search Cottages in Chestertown

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Cottages in Chestertown

Beautiful cottage on quiet country road walking distance to charming North Creek

9.8 out of 10, Exceptional, (41)
"Cute cozy cottage close to Gore mountain "
The price is SARĀ 676
SARĀ 979 total
includes taxes & fees
18 Jun - 19 Jun
Beautiful cottage on quiet country road walking distance to charming North Creek

Adirondack Mountains Cottage Near Gore Mountain!

9.8 out of 10, Exceptional, (110)
"We throughly enjoyed our stay and would like to return in the future."
Adirondack Mountains Cottage Near Gore Mountain!

Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

10.0 out of 10, Exceptional, (13)
"The house is tranquil, clean and well-equipped. My son and I were very comfortable, wish we could have been there more than 1 night. "
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

Charming cottage with a full kitchen, porch, & gas grill - walk to the lake

6.6 out of 10, (7)
"Perfect place away from the strip, so clean and well taken care of. I'd live there forever honestly."
Charming cottage with a full kitchen, porch, & gas grill - walk to the lake

Walk to Million Dollar Beach from this awesome Cottage!

10.0 out of 10, Exceptional, (152)
"Had a great time good location and plenty of room."
Walk to Million Dollar Beach from this awesome Cottage!

The Elms Waterfront Cottages

2.5 star property
8.2 out of 10, Very Good, (14)
"Don’t like the shower room . No shelf in the bathroom. The floor was not clean as well as the bathroom."
The price is SARĀ 769
SARĀ 853 total
includes taxes & fees
17 Jun - 18 Jun
The Elms Waterfront Cottages

New Lakeside Cottage 5 minutes from great hiking with large deck and lake view

10.0 out of 10, Exceptional, (20)
"Everything was perfect. The house is gorgeous and had everything we needed. Love the location too!"
New Lakeside Cottage 5 minutes from great hiking with large deck and lake view

Athol Vacation Rental w/ Mountain Views!

10.0 out of 10, Exceptional, (22)
"Beautiful facility, views, and a very quiet secluded place. The place was very clean and well supplied with amenities'."
Athol Vacation Rental w/ Mountain Views!

Beautiful lakeview cottage on Friends Lake

9.6 out of 10, Exceptional, (27)
"Very clean cabin, close to beach and lake. Host was very cordial. Expecting to return next summer."
Beautiful lakeview cottage on Friends Lake

Direct lakefront cottage with wood burning fireplace in great room. Pet friendly

8.4 out of 10, Very Good, (12)
"Nice waterfront location "
Direct lakefront cottage with wood burning fireplace in great room. Pet friendly

Lake Luzerne Cottage with Lake Rights 15 Min from Lake George

8.8 out of 10, Excellent, (31)
"I really enjoyed your cottage. Really clean and cozy. Excellent location. I would love too rent from you again next year."
Lake Luzerne Cottage with Lake Rights 15 Min from Lake George

Tree-lined dog-friendly cottage with wrap-around deck, grill, & gas fireplace

8.0 out of 10, Very Good, (2)
"The humble cabin was all that we needed. Near town, simple, a bit outdated"
Tree-lined dog-friendly cottage with wrap-around deck, grill, & gas fireplace

Beach Cottages at Lake George

3.0 star property
9.0 out of 10, Wonderful, (7)
"The cottage with 2 bedrooms was a cute tiny cottage. I didn't receive an email for the code to enter the cottage. After 2 phone calls, we did communicate with someone. We asked if we could leave the boat parked, and the person said it would be okay. Appreciative of that! Once inside the cottage, we found no toilet paper at all and had to go to the store. After a 4 1/2 hr drive to get there, we had to hit the road again. My family just slept, took showers and watched tv there. We did not use the...
Beach Cottages at Lake George

The Loon-ey Bin - Loon themed cottage less than 10 miles to Lake George

8.8 out of 10, Excellent, (25)
"Quiet cabin/home in walking distance to the lake. If you are looking for a quiet getaway, this is the perfect cabin. Only 20 mins from downtown lake George. I plan on staying here again next year!! "
The Loon-ey Bin - Loon themed cottage less than 10 miles to Lake George

Riverfront Cabin w/ Yard in Schroon Lake!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We needed a place for a few days to do some family matters in Schoon, this was Perfect because it let us bring our two dogs. They hade a great time. The Owner was Great with Comunication. Perfect place."
Riverfront Cabin w/ Yard in Schroon Lake!

A beautiful lake view cabin on Friends Lake

9.6 out of 10, Exceptional, (49)
"Another wonderful relaxing stay. So happy to have spent another week here. And same as last year every thing went smoothly and we had a great time exploring and visiting with family. Thank you Amanda for another great stay!"
A beautiful lake view cabin on Friends Lake

North Creek Cottage in the Adirondacks w/ Fire Pit

9.6 out of 10, Exceptional, (54)
"The house was easy to get to, well appointed and clean. Perfect for a few days skiing at Gore, and only a quick walk to dinner on the Main Street. Very happy and would stay again."
North Creek Cottage in the Adirondacks w/ Fire Pit

Private Adirondack lakefront Cottage on Loon Lake

10.0 out of 10, Exceptional, (7)
"My son and I recently bought a fishing boat With the private dock, it made things very convenient and an we had an enjoyable stay, love the lake and the surroundings, and the cottage was comfortable and well stocked."
Private Adirondack lakefront Cottage on Loon Lake

Bolton Landing Cottage w/ Deck, Walk to Beach!

9.8 out of 10, Exceptional, (27)
"Everything was exactly as it was supposed to be. Great place, very clean, perfect location. Loved the whole week there."
Bolton Landing Cottage w/ Deck, Walk to Beach!

Bluebear Cottage

9.4 out of 10, Exceptional, (3)
"We arrived to the property by way of country roads, quaint towns, and breath taking views of the lake. Once there we enjoyed all the property had to offer. The owners instructions were simple, the property was clean and they provided everything, including washing machines and soap. We had a blast and the hostess was amazing work with."
Bluebear 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

Frequently asked questions

How much do cottages in Chestertown cost?
Prices for cottages in Chestertown range between SAR 676 and SAR 769 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 158 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.
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!