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.
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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.
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Top-Rated Rentals and Accommodations in Chestertown
Recommended Vacation Rentals in Chestertown
Find your perfect vacation rental in Chestertown: from $90 per night
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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
- 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
37°
23°
41°
24°
42°
30°
44°
32°
33°
30°
32°
30°
35°
30°
Accommodations for your vacation in Chestertown
In Chestertown, two-thirds of the 231 properties are house rental, which represent 70.13% of its short-term accommodations. Interestingly, specific accommodation type, this type of accommodation in particular is $662 per night, with an average area of 188 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 10 currently listed. While house rental in Chestertown have an average size of 188 m², cabin have an average size of 56 m².
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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