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Compare 123 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, (194)
"Only stayed one night, but would have loved more with my whole family."
Hand-Crafted Cottage near Gore Mountain and Minerva Lake
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, (32)
"The cabin worked out well for our needs and at a good value. The owners were very communicative. I plan to use this place in the future as long as they have us. Thank you, Joe"
The price is SAR 619
SAR 811 total
includes taxes & fees
12 Jan - 13 Jan
Beautiful cottage on quiet country road walking distance to charming North Creek
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
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!
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 SAR 484
SAR 909 total
includes taxes & fees
12 Jan - 13 Jan
Lake Luzerne Cottage with Lake Rights 15 Min from Lake George
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
Adirondack Creekside Cottage-Sportmen’s Delight
Exterior

Adirondack Creekside Cottage-Sportmen’s Delight

10.0 out of 10, Exceptional, (47)
"House was super clean and had all we needed. Nice décor, and the pictures are accurate. Easy drive to Gore Mountain!Cathy was an excellent host, and the check-in and check-out were convenient and stress-free.Close to the road and truck traffic therefore some car noise noticeable at night. The heating equipment making some weird noise when starting maybe get it checked out. "
Adirondack Creekside Cottage-Sportmen’s Delight
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
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!
Housekeeping Cottage - near Lake George & Adirondacks - Belmont Special June 3-8
main entrance where code lock is located

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

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

9.2 out of 10, Wonderful, (69)
"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
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
#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
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, (19)
"We stayed at 35 Athol Rd during Christmas week. A fantastic house. Very spacious, yet comfortable and cozy. Incredibly well appointed. If you need something, you will find it in the house. Great location, secluded in the woods of the southern tier of the Adirondack Mountains. Yet, easy access to shopping stores. Yes, we enjoyed a white Christmas! And this house has easy access to outdoor winter activities!Cheers, Jack & Debbie"
Athol Vacation Rental w/ Mountain Views!
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, (103)
"Beautiful location and the space was super cozy. Will definitely be back!"
Adirondack Mountains Cottage Near Gore Mountain!
#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
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, (55)
"We could not have been happier or more comfortable in this spacious, yet cozy rental home. The property itself is so beautiful and peaceful. We used this as a home base for skiing at nearby (17 min away) Gore Mountain, and it was the perfect place to return to for an evening of relaxation by the fireplace. The hosts and property managers are lovely. "
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

9.0 out of 10, Wonderful, (16)
"Beautiful place wood location"
Cozy retreat with fireplace, kayaks, and shared beach/pond access
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 SAR 484 and SAR 619 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 123 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.