Chestertown Vacation Rentals

Compare 99 available properties from 12 providers
Chestertown
Anytime
2 guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Bed & Breakfast
Distance to center
Max. 1 mi
Max. 2 mi
Max. 3 mi
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

Recommended Vacation Rentals in Chestertown

Find your perfect vacation rental in Chestertown: from $75 per night

Private room Chestertown 2
Private room ∙ 2 guests ∙ 1 bedroom
Chestertown, Chester, New York, United States
from $78
Homestay.com
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Vacation Houses With Pools

House Pool Chestertown
Pool
House ∙ 2 guests ∙ 1 bedroom
Chestertown, Chester, New York, United States
from $150
Vrbo
5.0
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House Pool Chestertown
Pool
House ∙ 6 guests ∙ 4 bedrooms
Chestertown, Chester, New York, United States
from $204
Vrbo
4.8
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House Pool Chestertown
Pool
House ∙ 6 guests ∙ 3 bedrooms
Chestertown, Chester, New York, United States
from $159
Vrbo
4.5
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Dog-Friendly Vacation Rentals

House Pet-friendly Chestertown
Pet-friendly
House ∙ 4 guests ∙ 3 bedrooms
Chestertown, Chester, New York, United States
from $53
Vrbo
4.5
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House Pet-friendly Chestertown
Pet-friendly
House ∙ 4 guests ∙ 2 bedrooms
Chestertown, Chester, New York, United States
from $185
Vrbo
4.6
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House Pet-friendly Chestertown
Pet-friendly
House ∙ 4 guests ∙ 1 bedroom
Chestertown, Chester, New York, United States
from $156
Vrbo
4.7
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Best vacation rentals with a balcony

House Balcony Chestertown
Balcony
House ∙ 10 guests ∙ 3 bedrooms
Chestertown, Chester, New York, United States
from $400
Vrbo
4.8
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House Balcony Chestertown
Balcony
House ∙ 6 guests ∙ 3 bedrooms
Chestertown, Chester, New York, United States
from $415
Vacasa
3.8
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House Balcony Chestertown
Balcony
House ∙ 8 guests ∙ 4 bedrooms
Chestertown, Chester, New York, United States
from $313
Vacasa
4.4
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Popular Rental Amenities in Chestertown

  • Internet (72)
  • Parking (71)
  • No smoking (71)
  • Kitchen (65)
  • TV (65)
  • Microwave (65)
  • Grill (54)
  • Washer (42)
  • Fishing (38)
  • Fireplace (35)
  • Yard (24)
  • Air conditioning (24)

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, 198 rentals include "internet". So, if you can't imagine a vacation without internet, select the internet filter to compare these accommodations. Plan your vacation in advance if you love sweating the stress away in saunas or you want a rental with a pool. There are just 4 listed rentals including "saunas" and 6 properties including "pools."

The Weather in Chestertown

32°
12°
34°
12°
43°
21°
57°
34°
72°
46°
77°
54°
82°
59°
81°
57°
73°
48°
61°
39°
48°
28°
37°
23°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- 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.

Accommodations for your vacation in Chestertown

In Chestertown, two-thirds of the 99 properties are house rentals, which represent 70.64% of its short-term accommodations. Interestingly, specific accommodation type, this type of accommodation in particular is $393 per night, with an average area of 1,430 ft². Moreover, if you are going in a group of 8, house rentals are the perfect property type in Chestertown, as they usually welcome this exact group size. You can also consider other accommodation types in Chestertown. Hotel rooms are, for example, another popular accommodation type in this destination, with 7 currently listed. While house rentals in Chestertown have an average size of 1,430 ft², hotel rooms have an average size of 550 ft².

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.

Show all 99 properties
What are the best places to discover the arts and culture of Chestertown?

Chestertown souvenirs

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.

What are the best activities for families in Chestertown?

Family action

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.

Where are the unique attractions in Chestertown?

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.

We compare more than 1,300 providers, including:

Booking.com Vacation Rentals in Chestertown TripAdvisor Vacation Rentals in Chestertown Vrbo Vacation Rentals in Chestertown Airbnb Vacation Rentals in Chestertown VacationRentals.com Vacation Rentals in Chestertown HouseTrip Vacation Rentals in Chestertown FlipKey Vacation Rentals in Chestertown 9flats.com Vacation Rentals in Chestertown PerfectPlaces.com Vacation Rentals in Chestertown Homestay.com Vacation Rentals in Chestertown Only-apartments Vacation Rentals in Chestertown Interhome Vacation Rentals in Chestertown Bedycasa Vacation Rentals in Chestertown Novasol Vacation Rentals in Chestertown HomeEscape Vacation Rentals in Chestertown

Vacation Destinations Near Chestertown

Vacation Rentals

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