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Chestertown Vacation Rentals

Find 58 available offers from 6 partners
Chestertown
Anytime
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Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+
3.5+

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.

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Best Vacation Home Deals in Chestertown

Save up to 81%

House Chestertown
Dec 1 - Dec 8
-81%
$716
$138 per night
House ∙ 10 guests ∙ 3 bedrooms
Vacation Home in Brant Lake with Grill
4.7
Excellent (10 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
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House Chestertown
Apr 20 - Apr 27
-33%
$450
$300 per night
House ∙ 10 guests ∙ 4 bedrooms
Vacation Home in Chestertown with Grill & Yard + Amazing Views
4.9
Outstanding (56 ratings)
Chestertown, Chester, New York, United States
Details
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House Chestertown
Dec 1 - Dec 8
-61%
$662
$259 per night
House ∙ 6 guests ∙ 3 bedrooms
Wonderful House in Warrensburg with Grill
5.0
Outstanding
Chestertown, Chester, New York, United States
Details
Vacasa
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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

Book Vacation Rental Offers with the Highest User Rating

Cabin Chestertown
Oct 14 - Oct 21
$140 per night
Cabin ∙ 4 guests ∙ 1 bedroom
Lovely Cabin in Chestertown with Yard & Grill
4.8
Outstanding (33 ratings)
Chestertown, Chester, New York, United States
Details
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Cabin Chestertown
Oct 14 - Oct 21
$143 per night
Cabin ∙ 2 guests ∙ 1 bedroom
Cabin in Chestertown with Grill & Yard
4.7
Excellent (29 ratings)
Chestertown, Chester, New York, United States
Details
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Lodge Chestertown
Feb 2 - Feb 9
-25%
$330
$249 per night
Lodge ∙ 8 guests ∙ 3 bedrooms
Baby Friendly Lodge in Chestertown with Yard & Grill
5.0
Outstanding (24 ratings)
Chestertown, Chester, New York, United States
Details
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Recommended Vacation Rentals in Chestertown

Find your perfect vacation rental in Chestertown: from $95 per night

House Chestertown
Apr 19 - Apr 26
-18%
$193
$158 per night
House ∙ 8 guests ∙ 2 bedrooms
Vacation Home in Chestertown with Grill & Yard
5.0
Outstanding (6 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
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House Chestertown
Dec 2 - Dec 9
-81%
$589
$114 per night
House ∙ 6 guests ∙ 4 bedrooms
Beautiful Vacation Home in Chestertown
4.5
Excellent (1 rating)
Chestertown, Chester, New York, United States
Details
Vacasa
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Cottage Chestertown
Nov 11 - Nov 18
-59%
$286
$116 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
Lovely Cottage in Warrensburg with Grill & Yard + Trail View
4.2
Very good (14 ratings)
Chestertown, Chester, New York, United States
Details
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Chalet Chestertown
Oct 14 - Oct 21
-21%
$400
$318 per night
Chalet ∙ 8 guests ∙ 3 bedrooms
Chalet in Chestertown with Grill
4.9
Outstanding (27 ratings)
Chestertown, Chester, New York, United States
Details
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House Chestertown
Nov 3 - Nov 10
-76%
$4,445
$1,065 per night
House ∙ 25 guests ∙ 11 bedrooms
Wonderful Vacation Home in Chestertown with Grill & Yard
Chestertown, Chester, New York, United States
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House Chestertown
Apr 20 - Apr 27
-58%
$773
$327 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Warrensburg with Yard & Grill
5.0
Outstanding (1 rating)
Chestertown, Chester, New York, United States
Details
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House Chestertown
Dec 2 - Dec 9
-85%
$612
$93 per night
House ∙ 10 guests ∙ 3 bedrooms
Vacation Home in Brant Lake with Grill
4.5
Excellent
Chestertown, Chester, New York, United States
Details
Vacasa
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House Chestertown
Dec 16 - Dec 23
$315 per night
House ∙ 6 guests ∙ 3 bedrooms
Beautiful House in Chestertown with Grill
5.0
Outstanding (2 ratings)
Chestertown, Chester, New York, United States
Details
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House Chestertown
Nov 3 - Nov 10
-44%
$1,022
$575 per night
House ∙ 12 guests ∙ 6 bedrooms
Vacation Home in Chestertown with Yard & Grill
5.0
Outstanding (4 ratings)
Chestertown, Chester, New York, United States
Details
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Budget-friendly Vacation Rentals in Chestertown

Find Fantastic yet Inexpensive Offers

House Chestertown
Dec 16 - Dec 23
$200 per night
House ∙ 7 guests ∙ 3 bedrooms
House in Chestertown
Chestertown, Chester, New York, United States
Details
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Cottage Chestertown
Oct 21 - Oct 28
-60%
$357
$144 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
Wonderful Cottage in Warrensburg with Grill
Chestertown, Chester, New York, United States
Details
HomeToGo
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House Chestertown
Jan 5 - Jan 12
-61%
$438
$171 per night
House ∙ 8 guests ∙ 2 bedrooms
Vacation Home in Chestertown with Grill
Chestertown, Chester, New York, United States
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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.

House  Chestertown
Dec 16 - Dec 23
$214 per night
House ∙ 2 guests ∙ 1 bedroom
House in Chestertown with Outdoor Pool
4.7
Excellent (6 ratings)
Chestertown, Chester, New York, United States
Pool
Details
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Cabin  Chestertown
Dec 16 - Dec 23
$238 per night
Cabin ∙ 4 guests ∙ 2 bedrooms
Pleasant Cabin in Chestertown with Outdoor Pool
4.1
Very good (13 ratings)
Chestertown, Chester, New York, United States
Pool
Details
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House  Chestertown
Dec 16 - Dec 23
$238 per night
House ∙ 4 guests ∙ 2 bedrooms
Nice Vacation Home in Chestertown with Outdoor Pool
4.0
Very good (4 ratings)
Chestertown, Chester, New York, United States
Pool
Details
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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.

Cottage  Chestertown
Oct 20 - Oct 27
$173 per night
Cottage ∙ 6 guests ∙ 4 bedrooms
Cottage in Chestertown with Private Parking + Lake Views
4.7
Excellent (11 ratings)
Chestertown, Chester, New York, United States
Fishing
Details
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Cottage  Chestertown
Oct 21 - Oct 28
-25%
$138
$103 per night
Cottage ∙ 4 guests ∙ 3 bedrooms
Great Cottage in Chestertown with Yard & Grill
4.8
Outstanding (21 ratings)
Chestertown, Chester, New York, United States
Fishing
Details
Vrbo
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House  Chestertown
Dec 9 - Dec 16
-23%
$274
$212 per night
House ∙ 11 guests ∙ 4 bedrooms
Vacation Home in Chestertown with Yard & Grill
4.8
Outstanding (48 ratings)
Chestertown, Chester, New York, United States
Fishing
Details
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Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Chestertown rental with full kitchen.

Cabin  Chestertown
Dec 2 - Dec 9
-54%
$406
$186 per night
Cabin ∙ 8 guests ∙ 3 bedrooms
Cabin in Chestertown with Grill + Beautiful Views
5.0
Outstanding (3 ratings)
Chestertown, Chester, New York, United States
Kitchen
Details
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Cabin  Chestertown
Nov 11 - Nov 18
-61%
$371
$146 per night
Cabin ∙ 6 guests ∙ 2 bedrooms
Nice Cabin in Chestertown with Grill
5.0
Outstanding (5 ratings)
Chestertown, Chester, New York, United States
Kitchen
Details
Vrbo
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House  Chestertown
Nov 4 - Nov 11
-63%
$460
$170 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Chestertown with Grill + Beautiful Views
Chestertown, Chester, New York, United States
Free cancellation
Kitchen
Details
Evolve
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Popular Rental Amenities in Chestertown

  • Pet-friendly (23)
  • WiFi (64)
  • Air conditioning (56)
  • Pool (9)
  • Kitchen (59)
  • TV (63)
  • Parking (3)
  • Fishing (25)
  • Grill (60)
  • Washing machine (39)
  • No smoking (54)
  • Hot tub (3)

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

max.
Min.
32°
12°
15 days 15
max.
Min.
34°
12°
13 days 13
max.
Min.
43°
21°
13 days 13
max.
Min.
57°
34°
13 days 13
max.
Min.
72°
46°
14 days 14
max.
Min.
77°
54°
15 days 15
max.
Min.
82°
59°
14 days 14
max.
Min.
81°
57°
11 days 11
max.
Min.
73°
48°
11 days 11
max.
Min.
61°
39°
14 days 14
max.
Min.
48°
28°
11 days 11
max.
Min.
37°
23°
19 days 19
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.

7-Day Weather Forecast in Chestertown

Thu, 28 Sep
53°
46°

10%

0 h

2 mi/h

Fri, 29 Sep
60°
46°

10%

1 h

2 mi/h

Sat, 30 Sep
62°
50°

15%

1 h

2 mi/h

Sun, 1 Oct
66°
48°

0%

11 h

6 mi/h

Mon, 2 Oct
66°
48°

10%

11 h

3 mi/h

Tue, 3 Oct
55°
46°

10%

4 h

4 mi/h

Wed, 4 Oct
59°
51°

15%

0 h

5 mi/h

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.
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.

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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