Chestertown Vacation Rentals - HomeToGo base64Hash Chestertown Vacation Rentals - HomeToGo

Chestertown Vacation Rentals

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Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Distance to center
Max. 1 km
Max. 2 km
Max. 5 km
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 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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Save up to 68%

Best Vacation Home Deals in Chestertown

Cottage Chestertown
Apr 22 - Apr 29
-53%
$277
$130 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
Cottage in Warrensburg with Yard & Grill + Trail View
4.2
"Very good" (12 ratings)
Chestertown, Chester, New York, United States
Details
Evolve
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House Chestertown
Nov 11 - Nov 18
-68%
$507
$163 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Chestertown with Grill
5.0
"Excellent" (32 ratings)
Chestertown, Chester, New York, United States
Details
Vacasa
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House Chestertown
May 6 - May 13
-48%
$598
$309 per night
House ∙ 10 guests ∙ 5 bedrooms
House in Brant Lake with Hot Tub & Grill
4.8
"Excellent" (12 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
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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

House Chestertown
Feb 17 - Feb 24
-53%
$630
$296 per night
House ∙ 10 guests ∙ 5 bedrooms
House in Chestertown with Yard & Grill
4.7
"Outstanding" (141 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
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House Chestertown
Jun 10 - Jun 17
$350 per night
House ∙ 10 guests ∙ 4 bedrooms
Vacation Home in Chestertown with Grill & Yard + River Views
5.0
"Excellent" (54 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
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Cabin Chestertown
Jul 15 - Jul 22
$143 per night
Cabin ∙ 2 guests ∙ 1 bedroom
Cabin in Chestertown with Grill & Yard
4.7
"Outstanding" (25 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
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Recommended Vacation Rentals in Chestertown

Find your perfect vacation rental in Chestertown: from $90 per night

House Chestertown
May 6 - May 13
$744 per night
House ∙ 11 guests ∙ 6 bedrooms
Vacation Home in Chestertown with Grill
4.7
"Outstanding" (14 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
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House Chestertown
Sep 2 - Sep 9
$140 per night
House ∙ 4 guests ∙ 1 bedroom
Vacation Home in Chestertown with Seasonal Patio
Chestertown, Chester, New York, United States
Details
Vrbo
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Motel Chestertown
Jun 17 - Jun 24
$165 per night
Motel ∙ 4 guests ∙ 1 bedroom
Motel in Chestertown with Grill & Patio
4.6
"Outstanding" (110 ratings)
Chestertown, Chester, New York, United States
Details
Expedia
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House Chestertown
Jul 23 - Jul 30
$226 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Chestertown with Grill & Yard
Chestertown, Chester, New York, United States
Details
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Cabin Chestertown
Jun 10 - Jun 17
$238 per night
Cabin ∙ 4 guests ∙ 2 bedrooms
Pleasant Cabin in Chestertown with Outdoor Pool
4.0
"Very good" (12 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
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House Chestertown
Jun 10 - Jun 17
$215 per night
House ∙ 2 guests ∙ 1 bedroom
House in Chestertown with Outdoor Pool
4.7
"Outstanding" (6 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
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House Chestertown
Jun 10 - Jun 17
$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
Details
Vrbo
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Aparthotel Chestertown
Mar 25 - Apr 1
$166 per night
Aparthotel ∙ 6 guests ∙ 2 bedrooms
Aparthotel in Chestertown with Yard & Grill
4.4
"Very good" (6 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
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House Chestertown
Dec 16 - Dec 23
$406 per night
House ∙ 4 guests ∙ 6 bedrooms
Vacation Home in Chestertown with Grill & Yard
4.7
"Outstanding" (28 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
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Budget-friendly Vacation Rentals in Chestertown

Cabin Chestertown
Jun 24 - Jul 1
$140 per night
Cabin ∙ 4 guests ∙ 1 bedroom
Lovely Cabin in Chestertown with Yard & Grill
4.8
"Excellent" (33 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
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Cabin Chestertown
May 20 - May 27
$203 per night
Cabin ∙ 6 guests ∙ 2 bedrooms
Cabin in Chestertown with Grill
4.6
"Outstanding" (29 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
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House Chestertown
Mar 25 - Apr 1
-70%
$300
$90 per night
House ∙ 10 guests ∙ 3 bedrooms
Vacation Home in Brant Lake with Grill
5.0
"Excellent" (1 rating)
Chestertown, Chester, New York, United States
Details
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to Chestertown and book a vacation rental with air conditioning.

Lodge Air conditioning Chestertown
Feb 3 - Feb 10
-26%
$293
$216 per night
Lodge ∙ 8 guests ∙ 3 bedrooms
Baby Friendly Lodge in Chestertown with Yard & Grill
5.0
"Excellent" (4 ratings)
Chestertown, Chester, New York, United States
Air conditioning
Details
Vrbo
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House Air conditioning Chestertown
Apr 8 - Apr 15
$325 per night
House ∙ 10 guests ∙ 4 bedrooms
Child Friendly Vacation Home in Chester with Yard & Grill + Mountain Views
4.9
"Excellent" (84 ratings)
Chestertown, Chester, New York, United States
Air conditioning
Details
Vrbo
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House Air conditioning Chestertown
May 5 - May 12
-33%
$450
$300 per night
House ∙ 10 guests ∙ 4 bedrooms
Vacation Home in Chestertown with Grill & Yard + Amazing Views
5.0
"Excellent" (55 ratings)
Chestertown, Chester, New York, United States
Air conditioning
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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.

House Balcony Chestertown
May 5 - May 12
-27%
$398
$290 per night
House ∙ 10 guests ∙ 4 bedrooms
House in Chestertown with Yard & Grill
5.0
"Excellent" (1 rating)
Chestertown, Chester, New York, United States
Balcony
Details
Vrbo
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House Balcony Chestertown
Sep 23 - Sep 30
-35%
$327
$213 per night
House ∙ 8 guests ∙ 4 bedrooms
House in Chestertown with Grill
4.8
"Excellent" (16 ratings)
Chestertown, Chester, New York, United States
Balcony
Details
Vrbo
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House Balcony Chestertown
Oct 21 - Oct 28
-41%
$379
$225 per night
House ∙ 6 guests ∙ 4 bedrooms
House in Brant Lake with Grill & Yard + Meadow Views
4.0
"Very good" (2 ratings)
Chestertown, Chester, New York, United States
Balcony
Details
Vrbo
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Vacation Rentals With Fireplaces

Get warm and cozy on cold winter nights in Chestertown by booking a vacation home with a fireplace.

House Fireplace Chestertown
May 27 - Jun 3
$262 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Chestertown with Outdoor Pool
4.9
"Excellent" (14 ratings)
Chestertown, Chester, New York, United States
Fireplace
Details
Vrbo
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House Fireplace Chestertown
Apr 8 - Apr 15
$297 per night
House ∙ 6 guests ∙ 3 bedrooms
Beautiful House in Chestertown with Grill
5.0
"Excellent" (1 rating)
Chestertown, Chester, New York, United States
Fireplace
Details
Vrbo
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Cabin Fireplace Chestertown
Jan 5 - Jan 12
$205 per night
Cabin ∙ 6 guests ∙ 2 bedrooms
Cabin in Chestertown with Grill & Yard
4.8
"Excellent" (18 ratings)
Chestertown, Chester, New York, United States
Fireplace
Details
Vrbo
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Popular Rental Amenities in Chestertown

  • TV (78)
  • Microwave (78)
  • Internet (78)
  • Fireplace (77)
  • Kitchen (76)
  • Grill (73)
  • No smoking (69)
  • Air conditioning (65)
  • Yard (52)
  • No pets (51)
  • Washer (48)
  • Dishwasher (38)

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

max.
Min.
32°
12°
15 days 15
max.
Min.
34°
12°
13 days 13
max.
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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

Mon, 20 Mar
37°
23°

10%

6 h

7 mi/h

Tue, 21 Mar
41°
24°

15%

2 h

6 mi/h

Wed, 22 Mar
42°
30°

15%

0 h

4 mi/h

Thu, 23 Mar
44°
32°

15%

1 h

7 mi/h

Fri, 24 Mar
33°
30°

15%

0 h

1 mi/h

Sat, 25 Mar
32°
30°

15%

0 h

8 mi/h

Sun, 26 Mar
35°
30°

15%

1 h

10 mi/h

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.
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 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.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals in Chestertown TripAdvisor Vacation Rentals in Chestertown Vrbo Vacation Rentals in Chestertown VacationRentals.com Vacation Rentals in Chestertown HouseTrip Vacation Rentals in Chestertown FlipKey Vacation Rentals in Chestertown Homestay.com Vacation Rentals in Chestertown Only-apartments Vacation Rentals in Chestertown Interhome Vacation Rentals in Chestertown Novasol Vacation Rentals in Chestertown HomeEscape Vacation Rentals in Chestertown

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