Compare and find a welcoming rental for as little as $74 per night by searching and comparing the 69 properties listed in Chestertown. By comparing these accommodations, HomeToGo highlights the best deals and the most popular vacation homes in Chestertown.
Recommended Vacation Rentals in Chestertown
Rent a vacation accommodation in Chestertown: from $74 per night
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Popular Rental Amenities in Chestertown
The Weather in Chestertown
You can see our climate diagram above. During July, maximum temperatures go up to more than 82° On the contrary, the coolest month is January. The rainiest month is July while the driest month is August.
Get in touch with nature with a vacation home in Chestertown, New York
Not far from the Adirondack Mountain range, Chestertown is the perfect retreat for those wishing to get back to nature. Stunning wilderness, glistening lakes, and a charming local culture are yours to enjoy, in this scenic part of Upstate New York.
With its eclectic yet thoughtful collection of craft items, Rustic Charm is aptly named. Locally-made jewellery, decorative items, and more make for the perfect souvenirs, while the family-run shop also offers fun arts and crafts workshops.
Before heading off for you wilderness adventure, stop by The Crossroads to pick up some picnic items. Treat the kids to an ice cream - rumored to be the best in the area - and purchase local specialities such as boar meat and gluten-free beer. This is also the best place to buy your fishing equipment.
For an experience the kids won't forget, take them to Circle B Ranch. Based within Chestertown, the friendly team lead horse rides along excellent trails that take in some superb views. What's more, the horses are well-trained and well-looked-after.
For exciting water sports action, head over to Loon Lake Marina. Kids of all ages can have a go at waterskiing, stand-up paddle boarding, canoeing, and more, as you savor some quality family time.
Into the wild
Get a taste of the region's natural beauty with a visit to the 1,909-acre Cat and Thomas Mountains Preserve. Taking the yellow trail is highly recommended, due to the breathtaking views of Lake George and the Adirondacks, seen from the summit of Cat Mountain.
Characterised by the rugged cliffs that rise up alongside the Hudson River, the Hudson Gorge Wilderness Area is another top choice for keen hikers. The vast Pharaoh Lake Wilderness Area is also easily reached from your vacation home in Chestertown. With hidden ponds, the giant lake itself, and the 2,551-ft. Pharaoh Mountain, it's a true joy to explore.
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