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Compare 125 Cottages in Chestertown with updated reviews, rates, and availability.

Hand-Crafted Cottage near Gore Mountain and Minerva Lake
Pine cabin, Adirondack style
Hand-Crafted Cottage near Gore Mountain and Minerva Lake
10.0 out of 10, Exceptional, (186)
"Clean, well-equipped and comfortable. Cottage was close to the paddling and hiking we did."
Hand-Crafted Cottage near Gore Mountain and Minerva Lake
Adirondack Mountains Cottage Near Gore Mountain!
Warrensburg Vacation Rental | 2BR | 1BA | Riverfront Location | Step-Free Access
Adirondack Mountains Cottage Near Gore Mountain!
9.8 out of 10, Exceptional, (96)
"Great cottage/cabin with wonderful outdoor space. Pictures are true representation. Thoroughly relaxing and adventurous few days. "
Adirondack Mountains Cottage Near Gore Mountain!
Lakefront Home w/Fireplace near Lk George. Dog-friendly! Telecommuters welcome!
See how close this is to the water? Gas grill for your use.
Lakefront Home w/Fireplace near Lk George. Dog-friendly! Telecommuters welcome!
10.0 out of 10, Exceptional, (13)
"Amazing stay! Great area and lovely house to stay in for the weekend. Linda was amazing and the place was really clean with everything we needed!"
The price is SAR 908
SAR 1,509 total
includes taxes & fees
24 Sep - 25 Sep
Lakefront Home w/Fireplace near Lk George. Dog-friendly! Telecommuters welcome!
Reno done! Bolton Blue, Walk to Beach
Just a quick walk to Veteran's Beach
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 cottage on quiet country road walking distance to charming North Creek
Beautiful cottage on quiet country road walking distance to charming North Creek
9.8 out of 10, Exceptional, (27)
"Charming little cabin. Well stocked. Little trail down to the river right in front with a pool for the kids to play in. Highly recommend for quick and easy getaway from the capital."
The price is SAR 675
SAR 878 total
includes taxes & fees
28 Sep - 29 Sep
Beautiful cottage on quiet country road walking distance to charming North Creek
Athol Vacation Rental w/ Mountain Views!
Athol Vacation Rental | 1BR | 1.5BA | 1,500 Sq Ft | 5 Steps to Access
Athol Vacation Rental w/ Mountain Views!
10.0 out of 10, Exceptional, (13)
"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!
The Loon-ey Bin - Loon themed cottage less than 10 miles to Lake George
Property grounds
The Loon-ey Bin - Loon themed cottage less than 10 miles to Lake George
8.8 out of 10, Excellent, (24)
"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
Bolton Landing Cottage with Deck - Walk to Beach!
Bolton Landing Vacation Rental | 2BR | 2BA | 900 Sq Ft | 1 Story
Bolton Landing Cottage with Deck - Walk to Beach!
9.8 out of 10, Exceptional, (26)
"The cottage was very clean and comfortable. It was great having two bathrooms and a full kitchen. The convenience of being able to walk to everything in Bolton Landing is a plus."
Bolton Landing Cottage with Deck - Walk to Beach!
Beautiful Newly Built Cottage (14)
Exterior
Beautiful Newly Built Cottage (14)
Beautiful Newly Built Cottage (14)
Charming cottage with a full kitchen, porch, & gas grill - walk to the lake
Charming cottage with a full kitchen, porch, & gas grill - walk to the lake
6.4 out of 10, (6)
"should never be a Vrbo. Where do I start. electronic door locks wouldnt work, sign told us we couldnt use washer/dryer, had tape over front porch lite switch so couldnt se to try and unlock door, useless kitchen utensils, no micro, only tv was in the bedroom and it didnt have stations, just chromecast(which we didnt have).......ect. But it was clean"
Charming cottage with a full kitchen, porch, & gas grill - walk to the lake
An Adirondack Retreat
Parking at the front door, sunrise seating.
An Adirondack Retreat
9.4 out of 10, Exceptional, (67)
"Was very relaxing and just what we wanted away for long island traffic and trains we just enjoyed the back yard and the fire place and just chilled out we very much enjoyed it and Sue was a a great host aextento "
An Adirondack Retreat
Direct lakefront cottage with wood burning fireplace in great room. Pet friendly
Property grounds
Direct lakefront cottage with wood burning fireplace in great room. Pet friendly
8.4 out of 10, Very Good, (10)
"This property is in a beautiful location with lakefront view and its own dock, which we used. The house and its furnishings were rustic but we were comfortable. No AC but the nights were cool enough that it was comfortable to sleep. A few things need repairing like the back slider door handle."
Direct lakefront cottage with wood burning fireplace in great room. Pet friendly
#6 Lakeview @Birchwood Cottages at Loon Lake. Family Friendly Waterfront
#6 Lakeview @Birchwood Cottages at Loon Lake. Family Friendly Waterfront
9.6 out of 10, Exceptional, (13)
"We spent 3 Nights,mattress was comfortable and the location was quiet. Cabin was clean, with updated refrigerator, porch screens were in good condition. Enjoyed our visit, would recommend."
#6 Lakeview @Birchwood Cottages at Loon Lake. Family Friendly Waterfront
North Creek Cottage in the Adirondacks w/ Fire Pit
North Creek Vacation Rental | 2BR + Loft | 1BA | 1,000 Sq Ft | Stairs Required
North Creek Cottage in the Adirondacks w/ Fire Pit
9.6 out of 10, Exceptional, (49)
"The property was just as described. We enjoyed the firepit at night and the back porch for morning coffee. The location is easy walk to the little downtown shops and eateries. We also enjoyed a great meal at Basil and Wicks, too! "
North Creek Cottage in the Adirondacks w/ Fire Pit
Private Adirondack lakefront Cottage on Loon Lake
New dock added 7/2023. A great place to tie your boat or enjoy a morning coffee
Private Adirondack lakefront Cottage on Loon Lake
10.0 out of 10, Exceptional, (6)
"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
The Elms Waterfront Cottages
Lake view
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 SAR 1,241
SAR 1,378 total
includes taxes & fees
24 Sep - 25 Sep
The Elms Waterfront Cottages
Beach Cottages at Lake George
Room
Beach Cottages at Lake George
3.0 star property
9.0 out of 10, Wonderful, (7)
"The picture of the place was different smaller frigerator smaller space but my wife loved it . The area is very peaceful the property manager was very kind everything was smooth Nice place! Nice people!"
The price is SAR 718
SAR 797 total
includes taxes & fees
24 Sep - 25 Sep
Beach Cottages at Lake George
Cozy Cottage at Lake George Campsites!
Exterior
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!
Lakeside Cottage with Mountain Views
Property grounds
Lakeside Cottage with Mountain Views
10.0 out of 10, Exceptional, (1)
"Very nice accommodation. Three adults and a dog had plenty of room. Loved the covered and uncovered decks. Great views. Kitchen has everything you need, except food/ beverages. I definitely recommend it."
Lakeside Cottage with Mountain Views
Cottage - near Lake George & Adirondacks - year round
main entrance where code lock is located
Cottage - near Lake George & Adirondacks - year round
10.0 out of 10, Exceptional, (31)
"This cabin is clean and comfortable. It's conveniently located but far enough away from the activity to be very quiet. This was our second stay and we'll return when we get the opportunity​"
Cottage - near Lake George & Adirondacks - year round
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Other property types in Chestertown

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, (50)
"A gem in the Adirondacks. Quiet and peaceful carriage house on the Hudson River. Loved the rail bike ride, hiking and town of nearby Chestertown "
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Cozy retreat with fireplace, kayaks, and shared beach/pond access
Cozy retreat with fireplace, kayaks, and shared beach/pond access
9.2 out of 10, Wonderful, (13)
"We love the house super clean , the we love the area very peace and quiet , we love the private beach and the fresh air , definitely we be back again "
Cozy retreat with fireplace, kayaks, and shared beach/pond access
Peaceful Lakeside Retreat with Private Beach
Lake
Peaceful Lakeside Retreat with Private Beach
9.2 out of 10, Wonderful, (17)
"It was clean, nicely decorated, everything was new and in working order. Would suggest adding some face/wash cloths and top sheet for bed. Also, bed was comfortable but squeaked every time you made a move. All in all nice property and enjoyed our time :)"
Peaceful Lakeside Retreat with Private Beach
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 SAR205 and SAR367 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 125 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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