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

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

9.8 out of 10, Exceptional, (38)
"Charming cottage very close to Gore"
The price is SAR 619
SAR 814 total
includes taxes & fees
25 Mar - 26 Mar
Beautiful cottage on quiet country road walking distance to charming North Creek

Adirondack Mountains Cottage Near Gore Mountain!

9.8 out of 10, Exceptional, (106)
"We throughly enjoyed our stay and would like to return in the future."
Adirondack Mountains Cottage Near Gore Mountain!

Bolton Landing Cottage: Walk to Lake George!

9.8 out of 10, Exceptional, (40)
"Perfect place to plan and embark on your adventures or to wait out the bad weather. "
Bolton Landing Cottage: Walk to Lake George!

Bolton Landing Cottage w/ Deck, Walk to Beach!

9.8 out of 10, Exceptional, (27)
"My spouse and I were looking for a convenient base camp from which to explore the Lake George area. This property fit the bill! The house was small but well-stocked, with a full kitchen separating two bedrooms and bathrooms. Walkable neighborhood with local shops, restaurants, brewery, deli, laundry, and ice cream made this a perfect choice. If you enjoy sunrises, the park and beach across the street were a 2-minute stroll. Tennis and pickleball courts were also conveniently located behind the...
Bolton Landing Cottage w/ Deck, Walk to Beach!

Hand-Crafted Cottage near Gore Mountain and Minerva Lake

10.0 out of 10, Exceptional, (201)
"Great stay and exactly as described. Loved the wood stove and cozy living room, lots of space for the kids upstairs. On a very quiet road."
Hand-Crafted Cottage near Gore Mountain and Minerva Lake

Reno done! Bolton Blue, Walk to Beach

2.0 star property
10.0 out of 10, Exceptional, (3)
"We are long-time summer residents who needed alternative housing. We are so glad that we were able to rent this home. You walk in the door, and just wow. The view is 180 degrees of mountains, lake, and clouds. You can just enjoy the view all day. Everything was well stocked and comfortable. Beds were great. The dining room-kitchen area made for easy cooking and dining. Wonderful deck for watching sunsets. This is a perfect place for family time, and everyone had plenty of privacy. It's a retreat...
Reno done! Bolton Blue, Walk to Beach

Beautiful lakeview cottage on Friends Lake

9.6 out of 10, Exceptional, (27)
"Great, comfortable little cottage. The owner has thought to supply just about everything you could need. It was clean and fresh. There was an area wide power outage when we arrived due to a big storm. The owner had taken the time to hook up a generator so we had a light and power to the refrigerator. Power was back on in a couple of hours. We would absolutely stay there again. Our dog absolutely loved the front deck overlooking a view of the lake through the trees."
Beautiful lakeview cottage on Friends Lake

Bolton Landing Cottage w/ Deck, Walk to Beach!

3.0 star property
Bolton Landing Cottage w/ Deck, Walk to Beach!

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

8.6 out of 10, Excellent, (11)
"Nice waterfront location "
Direct lakefront cottage with wood burning fireplace in great room. Pet friendly

Housekeeping Cottage - near Lake George & Adirondacks - Belmont Special June 3-8

10.0 out of 10, Exceptional, (34)
"We had a great weekend at this location. It's minutes away from Six Flags and close to good restaurants. Hosts were very easy to work with. "
Housekeeping Cottage - near Lake George & Adirondacks - Belmont Special June 3-8

Athol Vacation Rental w/ Mountain Views!

10.0 out of 10, Exceptional, (20)
"Very cozy and private. The location is just close enough to everything that it is not to far to drive into towns, but still has the feeling that you are in the mountains. The inside is beautiful. "
Athol Vacation Rental w/ Mountain Views!

Adirondack Creekside Cottage-Sportmen’s Delight

10.0 out of 10, Exceptional, (52)
"Nice clean place. Close to the mountains."
Adirondack Creekside Cottage-Sportmen’s Delight

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

Three Hurricanes Landing - 3 Bedroom Cottage on the Beautiful Hudson River

9.8 out of 10, Exceptional, (46)
"My family and I got to enjoy a wonderful, relaxing week at this beautiful waterside home. Right on the Hudson River. Fishing off the dock. Able to just put the kayaks and paddle boards right in at any time and enjoy sunrise and sunsets on the water. Grill and outside table to enjoy meals together. Check in and check out process were very easy and we even received a little check in gift 😀 The host was very responsive and kind We would have stayed another week or more if we could. We...
Three Hurricanes Landing - 3 Bedroom Cottage on the Beautiful Hudson River

North Creek Cottage in the Adirondacks w/ Fire Pit

9.6 out of 10, Exceptional, (53)
"Everything was very well equipped and comfortable. Would definitely look to stay here again!"
North Creek Cottage in the Adirondacks w/ Fire Pit

Cozy Cottage at Lake George Campsites!

4.0 out of 10, (2)
"Property is beautiful BUT beware the cabins are much smaller than they appear in the photos. The upstairs with the 2 beds is just a crawl space with beds. Not suitable for young kids or anyone tall lol. The steps leading up to that space is dangerous. Make sure to buy the linen package, i didnt even know it exsisted until we arrived and it was to late to purchase. Beware of the slippery floors as well, my kids took many spills on them. The bunkbeds are also in closet NOT room. "
Cozy Cottage at Lake George Campsites!

Walk to Million Dollar Beach from this awesome Cottage!

10.0 out of 10, Exceptional, (151)
"This is our third time staying at this property. Each and every time, I am so sad to leave. The hosts are fantastic and answer promptly any questions we may have. This property is so beautiful and we can't wait to come back again next spring."
Walk to Million Dollar Beach from this awesome Cottage!

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

10.0 out of 10, Exceptional, (19)
"Everything about this property is how it should be and accommodating small animals is even a bonus. The owners/hosts are easy to communicate w and eager to make your stay comfortable. Everything extra you may need is here. Thank you to the Kiel’s! "
New Lakeside Cottage 5 minutes from great hiking with large deck and lake view

Waterfront Home on Lake George w/ Boat Dock!

3.0 star property
Waterfront Home on Lake George w/ Boat Dock!

Private Cottage on Lake George W/ Wood-Burning Fireplace, Lake View, & Fast WiFi

9.4 out of 10, Exceptional, (23)
"Stayed there with my husband, daughters, kids and brother for Mom’s 90th birthday!! Plenty of space and cute place!!!"
Private Cottage on Lake George W/ Wood-Burning Fireplace, Lake View, & Fast WiFi
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

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

10.0 out of 10, Exceptional, (60)
"My family and i had a great time here! The place is Amazing and we would definitely stay again! "
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

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

9.2 out of 10, Wonderful, (36)
"Plenty of room for everyone, warm and relaxing."
Lakefront cabin with beautiful loft, game room, views, private dock

Year round Log Cabin on Loon Lake. Minutes from skiing at Gore Mountain

9.8 out of 10, Exceptional, (84)
"Wonderful stay. Owner very accomodating. We had everything we needed."
Year round Log Cabin on Loon Lake. Minutes from skiing at Gore Mountain
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?
Prices for cottages in Chestertown range between and 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 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!
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.