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
Save up to 81%
Compare and find a welcoming rental for as little as $95 per night by searching and comparing the 58 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
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Recommended Vacation Rentals in Chestertown
Find your perfect vacation rental in Chestertown: from $95 per night
Budget-friendly Vacation Rentals in Chestertown
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Vacation Houses With Pools
Make a splash on your next vacation! Over 16% of in Chestertown vacation rentals have a swimming pool.
Vacation Homes With Fishing Spots Nearby
Hoping to catch a few fish on your next vacation? Check out these amazing rentals in Chestertown with fishing spots nearby.
Apartments and vacation rentals with a kitchen
Cook up a feast on your next vacation and book a Chestertown rental with full kitchen.
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, 23 rentals include "Pets allowed". So, if you bring your pet everywhere, select the Pets allowed filter to compare these accommodations. Plan your vacation in advance if you need a fenced-in backyard or you need wheelchair access. There are just 1 listed rentals including "Fenced" and 3 properties including "Wheelchair accessible."
The Weather in Chestertown
- Rainy days
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
53°
46°
60°
46°
62°
50°
66°
48°
66°
48°
55°
46°
59°
51°
Accommodations for your vacation in Chestertown
In Chestertown, many of the 58 properties are house rental, which represent 61.9% of its short-term accommodations. Interestingly, specific accommodation type, this type of accommodation in particular is $508 per night, with an average area of 205 m². Moreover, if you are going in a group of 9, house rental are the perfect property type in Chestertown, as they usually welcome this exact group size. You can also consider other accommodation types in Chestertown. Cabin are, for example, another popular accommodation type in this destination, with 7 currently listed. While house rental in Chestertown have an average size of 205 m², cabin have an average size of 56 m².
Information about vacation rentals in Chestertown
| 🏡 Vacation rentals available | 58 homes |
|---|---|
| 💳 Possible discounts | up to 62% |
| 🌙 Nightly prices starting at | $95 |
| ⭐ Popular amenities | Pets allowed, Internet and Air conditioning |
| 🐾 Pet friendly homes | 20 homes |
| 🏊 Vacation rentals with pools | 9 homes |
Frequently Asked Questions
What is the typical price per night for a vacation rental in Chestertown?
The price of a night's stay in Chestertown starts at $95. If you would like to stay in a house rental, the average price is $508 per night. A cabin Chestertown will cost on average $268 per night.
How many vacation rentals are available for booking in Chestertown?
There are 58 rentals available for booking for your upcoming trip.
What amenities are most popular for vacation rentals in Chestertown?
Usually travelers search for Internet, Pets allowed, and Air conditioning when booking a vacation rental in Chestertown.
How many vacation homes with pools are there in Chestertown?
There are 9 rentals across 6 providers in Chestertown.
Are dogs allowed in vacation homes in Chestertown?
Yes, there are 20 vacation rentals in Chestertown that allow dogs and the average nightly price is $337.
What's the best time to travel to Chestertown?
July and August are the warmest months in Chestertown with temperatures around 82 °F. The coldest months in Chestertown are January and February, with 12 °F on average.
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