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Compare 120 Cottages in Chestertown with updated reviews, rates, and availability.

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
8.6 out of 10, Excellent, (11)
"Nice waterfront location "
Direct lakefront cottage with wood burning fireplace in great room. Pet friendly
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!"
Lakefront Home w/Fireplace near Lk George. Dog-friendly! Telecommuters welcome!
Pine Knoll on Lake George | Cottage with direct lake & private dock access
Pine Knoll on Lake George | Cottage with direct lake & private dock access
9.8 out of 10, Exceptional, (6)
"Wonderful hosts. Very secluded home on the shores of Lake George. Warm and cozy inside. Many places to visit. "
Pine Knoll on Lake George | Cottage with direct lake & private dock access
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, (17)
"Wonderful place as described. Everything that we needed was there. Very clean easy to find "
Athol Vacation Rental w/ Mountain Views!
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
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, (190)
"The pictures don't even do it justice! Our new favorite place to stay in the Adirondacks. Can't wait to go back!"
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, (102)
"Very cozy and nice"
Adirondack Mountains Cottage Near Gore Mountain!
Bolton Landing Cottage: Walk to Lake George!
Bolton Landing Vacation Rental | 1BR | 1BA | 500 Sq Ft | 1 Story
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!
Beach Cottages at Lake George
Room
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
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!
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, (33)
"Stayed for 4 nights. We didn’t spend a lot of time in the cottage, but it was pefect for us. Great location"
Cottage - near Lake George & Adirondacks - year round
Adirondack Creekside Cottage-Sportmen’s Delight
Exterior
Adirondack Creekside Cottage-Sportmen’s Delight
10.0 out of 10, Exceptional, (45)
"Very clean, excellent stay host was great to work with. Highly recommended 😊"
Adirondack Creekside Cottage-Sportmen’s Delight
Beautiful cottage on quiet country road walking distance to charming North Creek
Exterior
Beautiful cottage on quiet country road walking distance to charming North Creek
9.8 out of 10, Exceptional, (31)
"Excellent experience. "
The price is AED 606
AED 797 total
includes taxes & fees
20 Nov - 21 Nov
Beautiful cottage on quiet country road walking distance to charming North Creek
Lake Luzerne Cottage with Lake Rights 15 Min from Lake George
Living area
Lake Luzerne Cottage with Lake Rights 15 Min from Lake George
9.2 out of 10, Wonderful, (25)
"We truly enjoyed our stay in this very quaint and cozy cottage home and it was perfect for my family of 3. We loved the peace and quiet at night and our only regret is that we didn’t book a longer stay. Our Hosts were very communicative when we had any questions. We will definitely love to book another stay in the future."
The price is AED 474
AED 893 total
includes taxes & fees
26 Nov - 27 Nov
Lake Luzerne Cottage with Lake Rights 15 Min from Lake George
Private Cottage on Lake George W/ Wood-Burning Fireplace, Lake View, & Fast WiFi
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
An Adirondack Retreat
Parking at the front door, sunrise seating.
An Adirondack Retreat
9.4 out of 10, Exceptional, (68)
"The cottage was very clean with an extremely comfortable bed and well-stocked modern kitchen with quality appliances. Lots of windows which overlooked a beautiful backyard with mature trees made out stay relaxing. Quiet and peaceful setting "
An Adirondack Retreat
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
Exterior
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
9.6 out of 10, Exceptional, (15)
"Very nice just terrain was rough handicap person"
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
Glen Cottage at Cozy Nook
Terrace/patio
Glen Cottage at Cozy Nook
9.6 out of 10, Exceptional, (11)
"Very clean and functional. We ran in to zero issues with this place and absolutely loved the neighborhood/attractions in and around the community! 100% recommend"
Glen Cottage at Cozy Nook
#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
Swim area. What a view!
#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
9.6 out of 10, Exceptional, (11)
"Arrived around 5 on Saturday. Great location. Once I figured out how to open key holder, we moved in. We enjoyed our cabin, found the information folders helpful. We had a nice fire and enjoyed our stay. Our suggestions for improvement. The light in the main room was very bright. A dimmer light switch would have been appreciated. Would like to have had a reading light on both sides of the bed."
#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
Huckleberry Cottage at Cozy Nook
Outdoor dining
Huckleberry Cottage at Cozy Nook
9.6 out of 10, Exceptional, (15)
"Nice and peaceful. "
Huckleberry Cottage at Cozy Nook
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

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
Cozy retreat with fireplace, kayaks, and shared beach/pond access
Cozy retreat with fireplace, kayaks, and shared beach/pond access
9.0 out of 10, Wonderful, (16)
"Beautiful place wood location"
Cozy retreat with fireplace, kayaks, and shared beach/pond access
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, (53)
"Host John was like best of friends. Couldn’t have done more for us. Sue too was very nice. Pearl and ruby, their do"
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
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 AED 474 and AED 606 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 120 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?
With Expedia’s convenient filter tool, comparing cheap cottages in Chestertown is a breeze. To view accommodations that’ll make your wallet happy, fine-tune your search results by star rating, amenities and budget.