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Browse Select Chestertown Cottages

Adirondack Mountains Cottage Near Gore Mountain!
9.8 out of 10, Exceptional, (89)
"Loved it. Cozy cabin by the river. Easy access. Great view of the Hudson and loved watching the squirrels. We were all very pleased."
Adirondack Mountains Cottage Near Gore Mountain!
Adirondack Creekside Cottage-Sportmen’s Delight
10.0 out of 10, Exceptional, (36)
"Great time awesome fishing cottage was super clean and maintained"
Adirondack Creekside Cottage-Sportmen’s Delight
Beautiful cottage on quiet country road walking distance to charming North Creek
9.8 out of 10, Exceptional, (26)
"Thank you for letting us stay @ your beautiful cottage. You went above & beyond. Very homey accommodations & thank you for being so flexible & allowing us to stay another night."
The price is £171
per night
11 Jun - 12 Jun
Beautiful cottage on quiet country road walking distance to charming North Creek
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Cottage - near Lake George & Adirondacks - year round
10.0 out of 10, Exceptional, (27)
"Much of the typical Lake George activities were closed since we visited during April, but we were very happy to stay here and will definitely return! It was the perfect space for us two (with extra to fit an additional friend or 2). Owner provided towels, pans, grill, coffee, etc for the stay which is greatly appreciated. It was close distance to anywhere we needed to go for groceries, activities, stores! Sad to go but I look forward to future travels here :)"
Cottage - near Lake George & Adirondacks - year round
Hand-Crafted Cottage near Gore Mountain and Minerva Lake
10.0 out of 10, Exceptional, (179)
"This is an amazing place! The cabin is so cozy, we didn't want to leave. It was clean, well equipped, great lay-out. Beautiful area with lots of outdoor activities close by. I hope to come back again!"
Hand-Crafted Cottage near Gore Mountain and Minerva Lake
Direct lakefront cottage with wood burning fireplace in great room. Pet friendly
9.6 out of 10, Exceptional, (4)
"Cabin was clean and cozy and in a quiet location. Make sure you build the fire as far back in the fireplace as possible or you will be smoked out.The kitchen needs a frying pan or two. Overall we were very comfortable."
Direct lakefront cottage with wood burning fireplace in great room. Pet friendly
Pine Knoll on Lake George | Cottage with direct lake & private dock access
9.4 out of 10, Exceptional, (3)
"As an everyday workers, this place was the best therapy to rest, to share and to connect with nature!!!"
Pine Knoll on Lake George | Cottage with direct lake & private dock access
Athol Vacation Rental w/ Mountain Views!
10.0 out of 10, Exceptional, (5)
"Wonderful location, nice house with all the amenities."
Athol Vacation Rental w/ Mountain Views!
#6 Lakeview @Birchwood Cottages at Loon Lake. Family Friendly Waterfront
9.8 out of 10, Exceptional, (11)
"Owners were very accommodating. Sitting around campfire with family. Beach right across the road. Great awesome fun time. Definitely will be back"
#6 Lakeview @Birchwood Cottages at Loon Lake. Family Friendly Waterfront
Private Adirondack lakefront Cottage on Loon Lake
10.0 out of 10, Exceptional, (4)
"The cabin is exactly as described in the listing - it is very clean, welcoming, and tastefully decorated! Although we visited the town's public beach one day, we did appreciate having a private area on the beach. The host was great with communication. There is plenty to do in the area - our family went Horseback riding at Circle B Ranch, rail biking riding in North Creek, and took a summer ski lift ride up Gore Mountain. We also visited the farmer's market in Chestertown. Our family is from...
Private Adirondack lakefront Cottage on Loon Lake
Waterfront Home w/Fireplace near Lk George. Americade! Telecommuters welcome!
10.0 out of 10, Exceptional, (7)
"Some friends and I stayed in this lovely home on our way to see the eclipse and everything was wonderful; super responsive hosts, clear directions, a home that was perfectly ready for us. Bummer we only stayed the one night, would love to come back and stay longer!"
Waterfront Home w/Fireplace near Lk George. Americade! Telecommuters welcome!
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
Bluebear Cottage
9.0 out of 10, Wonderful, (2)
"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
Lakefront Rustic Cottage with Direct Lake Access
10.0 out of 10, Exceptional, (1)
"Small but all you need. Very relaxing. I enjoyed my stay immensely."
Lakefront Rustic Cottage with Direct Lake Access
Cottage by the lake
8.0 out of 10, Very good, (4)
"Property and photos as advertised. Owner kept in contact to ensure all was ok. Cabin/house clean, air conditioned. Proximity to marina named Hulett Landing was good. Marina had basic essentials. Would recommend this cabin and stay there again."
Cottage by the lake
Lake Luzerne Cottage with Lake Rights 15 Min from Lake George
9.2 out of 10, Wonderful, (16)
"Property is very nice and comfortable, and very nicely decorated. The bedrooms had a lot of space, the beds were very comfortable, and the furnishings were very retro, but stately (I love retro style!). Lots of sunshine from the windows. Kitchen is small, but adequate. The front porch was very nice and relaxing - I wish I could’ve enjoyed it longer. I really have no complaints except that I didn’t book a longer stay! I would love to come back to it and stay longer!"
The price is £163
per night
13 Jun - 14 Jun
Lake Luzerne Cottage with Lake Rights 15 Min from Lake George
Private Cottage on Lake George W/ Wood-Burning Fireplace, Lake View, & Fast WiFi
9.4 out of 10, Exceptional, (21)
"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
9.4 out of 10, Exceptional, (61)
"It was a fine stay, would do it again"
An Adirondack Retreat
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
9.6 out of 10, Exceptional, (14)
"We really enjoyed our stay and the views were awesome. We’ve been vacationing in the Adirondack Mountains for many years but didn’t know that Birchwood Cottages was a place that you could stay. We’ve always stayed at the Maple Leaf up in Schroon Lake. We now plan to make Loon Lake a yearly thing."
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
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
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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.

Other property types in Chestertown

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
10.0 out of 10, Exceptional, (39)
"The place was amazing!!! So clean and had everything you need to stay away from home!!! Our do Oliver especially loved playing with Ruby and Pearl!!!"
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Private child-friendly home with game room, high-speed WiFi, and wraparound deck
9.8 out of 10, Exceptional, (48)
"Clean property. Kids enjoyed games in basement."
Private child-friendly home with game room, high-speed WiFi, and wraparound deck
Cozy retreat with fireplace, kayaks, and shared beach/pond access
8.8 out of 10, Excellent, (9)
"We loved the days we stayed there, beautiful environment, very nice view. Be careful with the mosquitos, they came out in the evening."
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.

Chestertown Cottages information

Number of reviews
487
Accommodation
117 Cottages
Lowest Price
£163
Highest Price
£171

Frequently asked questions

How much do holiday cottages in Chestertown cost?
Prices for holiday cottages in Chestertown range between £163 and £171 per night. No matter your budget, you’ll find a perfect place to get in tune with nature. This price was 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 holiday cottages are there in Chestertown?
You can choose from 117 holiday cottages in Chestertown. No matter if you’re travelling with the kids or organising a weekend break with your buddies, Expedia can help you find the ideal place to reconnect with nature.
Are there any family-friendly holiday cottages in Chestertown?
Yes, there certainly are! Lock in Sunset Mountain Lodge, a terrific base for discovering the great outdoors in Chestertown. This family-friendly cottage has a 3-star rating and offers useful amenities like a playground and a nearby beach. Once you’ve checked in and unpacked, there are loads of family-friendly attractions to discover in and around Chestertown. Natural Stone Bridge and Caves and Loon Lake Beach are two popular options.
Why book your cottage in Chestertown with Expedia?
Reserving a cottage in Chestertown is as simple as working out your travel dates and selecting your ideal place for outdoor fun and relaxation. From upscale retreats to low-cost properties and holiday cottages that feature amenities like a kitchenette, Expedia has something for all tastes and styles. As for terrific deals? We’ve got them as well!
How can I find cheap cottages in Chestertown?
A great way to uncover cheap cottages in Chestertown is with Expedia’s convenient filter tool. Refine your search by star rating, budget and amenities to nab awesome bargains with only a few clicks.
What is there to do in Chestertown near my cottage?
There are loads of wonderful things to do in Chestertown. Discover well-known attractions like Loon Lake Beach, Natural Stone Bridge and Caves and Friends Lake. Avalanche Lake, Loon Lake and Tripp Pond are other highlights.

Chestertown Hotel Reviews
Expedia verified reviews