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.
Choose the perfect vacation rental
Best Vacation Home Deals in Chestertown
Compare and find a welcoming rental for as little as $90 per night by searching and comparing the 231 properties listed in Chestertown. By comparing these accommodations, HomeToGo highlights the best deals and the most popular vacation homes in Chestertown.
Top-Rated Rentals and Accommodations in Chestertown
Recommended Vacation Rentals in Chestertown
Find your perfect vacation rental in Chestertown: from $90 per night
Budget-friendly Vacation Rentals in Chestertown
Vacation rentals and apartments with air conditioning
Keep cool during your trip to Chestertown and book a vacation rental with air conditioning.
Best vacation rentals with a balcony
Looking for a home with a balcony? Check out these vacation homes in Chestertown with their own private patios and balconies.
Vacation Rentals With Fireplaces
Get warm and cozy on cold winter nights in Chestertown by booking a vacation home with a fireplace.
Popular Rental Amenities in Chestertown
Accommodations can be chosen based on various criteria. Above, you can see the number of rentals that include a specific amenity in Chestertown. In Chestertown, 78 rentals include "TV". So, if you want to tune out with some TV time, select the TV filter to compare these accommodations. Plan your vacation in advance if you want a rental with a jacuzzi or you want a rental with a balcony or a patio. There are just 4 listed rentals including "Fenced" and 5 properties including "Smoking."
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 December while the driest month is August.
7-Day Weather Forecast in Chestertown
Accommodations for your vacation in Chestertown
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.
Information about vacation rentals in Chestertown
|🏡 Vacation rentals||231 properties|
|💳 Possible discounts||up to 66%|
|🌙 Nightly prices starting at||$90|
|⭐ Popular amenities||TV, Microwave and Internet|
|🐾 Pet friendly accommodations||24 properties|
|🏊 Vacation rentals with pools||17 properties|
Frequently Asked Questions
What is the price per night for a vacation home in Chestertown?
The price of a night's stay in Chestertown starts at $90. If you’re interested in a house rental, the average price is $662 per night. A cabin Chestertown will cost $264 per night on average.
How many vacation homes are available for booking in Chestertown?
Currently there are 231 vacation homes to choose from for your vacation.
What amenities are most popular for vacation homes in Chestertown?
Three most popular amenities for vacation rentals in Chestertown include accommodations with: TV, Microwave, and Internet.
How many vacation homes with pools are in Chestertown?
Check out 17 vacation rentals available to book in Chestertown.
Are pets allowed in vacation rentals in Chestertown?
Yes, currently there are 24 vacation homes in Chestertown that allow pets and the average nightly rate is $359.
When is it better to travel to Chestertown?
July and August are usually the warmest months in Chestertown with temperatures around 82 °F. January and February in Chestertown are the coldest, with 12 °F on average.
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