Find Vacation Rentals in Chestertown

We have 58 properties to choose from
Chestertown
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Popular Chestertown Vacation Rentals

Find the perfect Chestertown vacation rental

House Chestertown
$264 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding
Chestertown, Chester, New York, United States
Details
Vacasa
Details
Details
House Chestertown
$164 per night
House ∙ 6 guests ∙ 4 bedrooms
4.5
Excellent (1 rating)
Chestertown, Chester, New York, United States
Details
Vacasa
Details
Details
House Chestertown
$189 per night
House ∙ 8 guests ∙ 2 bedrooms
5.0
Outstanding (6 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
Details
Details
House Chestertown
$186 per night
House ∙ 10 guests ∙ 3 bedrooms
4.7
Excellent (10 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
Details
Details
House Chestertown
$363 per night
House ∙ 10 guests ∙ 4 bedrooms
4.9
Outstanding (54 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
Details
Details
Cabin Chestertown
$156 per night
Cabin ∙ 4 guests ∙ 1 bedroom
4.8
Outstanding (33 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
Details
Details
Cabin Chestertown
$160 per night
Cabin ∙ 2 guests ∙ 1 bedroom
4.7
Excellent (29 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
Details
Details
Lodge Chestertown
$272 per night
Lodge ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (24 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
Details
Details
Cottage Chestertown
$189 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
4.2
Very good (14 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
Details
Details
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Recommended Rentals With Pools

Cabin  Chestertown
$284 per night
Cabin ∙ 4 guests ∙ 2 bedrooms
4.1
Very good (13 ratings)
Chestertown, Chester, New York, United States
Pool
Details
Vrbo
Details
Details
House  Chestertown
$239 per night
House ∙ 2 guests ∙ 1 bedroom
4.7
Excellent (6 ratings)
Chestertown, Chester, New York, United States
Pool
Details
Vrbo
Details
Details
House  Chestertown
$264 per night
House ∙ 4 guests ∙ 2 bedrooms
4.0
Very good (4 ratings)
Chestertown, Chester, New York, United States
Pool
Details
Vrbo
Details
Details
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Pet-Friendly Homes and Apartments

House  Chestertown
$323 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (1 rating)
Chestertown, Chester, New York, United States
Pet-friendly
Details
Vrbo
Details
Details
House  Chestertown
$142 per night
House ∙ 10 guests ∙ 3 bedrooms
4.5
Excellent
Chestertown, Chester, New York, United States
Pet-friendly
Details
Vacasa
Details
Details
House  Chestertown
$235 per night
House ∙ 7 guests ∙ 3 bedrooms
Chestertown, Chester, New York, United States
Pet-friendly
Details
Vrbo
Details
Details
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Best vacation rentals with a balcony

House  Chestertown
$294 per night
House ∙ 6 guests ∙ 4 bedrooms
4.5
Excellent (4 ratings)
Chestertown, Chester, New York, United States
Balcony
Details
Vrbo
Details
Details
House  Chestertown
$437 per night
House ∙ 6 guests ∙ 3 bedrooms
Chestertown, Chester, New York, United States
Balcony
Details
Vrbo
Details
Details
House  Chestertown
$417 per night
House ∙ 8 guests ∙ 4 bedrooms
4.5
Excellent (1 rating)
Chestertown, Chester, New York, United States
Balcony
Details
Vacasa
Details
Details
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Frequently Asked Questions

How much does a night in a vacation rental cost in Chestertown on average?

Accommodation in Chestertown cost from $142 per night.

Is it possible to compare multiple vacation rentals in Chestertown?

Our large collection of vacation homes makes it easy to filter and compare 58 offers in Chestertown.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Chestertown

Looking for a vacation rental in Chestertown? Tripping.com has 48 vacation rental homes available in Chestertown. You'll find 0 studios, 12 1-bedroom, 12 2-bedroom and 24 rentals with 3 or more bedrooms ranging from $47 a night. For extra convenience, many of these vacation homes can be booked directly online. The average price of a nightly rental in Chestertown is $219 while the average price of a weekly rental is $25. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Chestertown home is $25. Wondering if you can bring your dog or cat along with you? There are 17 pet-friendly vacation rentals available in Chestertown. In addition to accommodating pets, Chestertown rentals offer a variety of amenities. In particular, 46 rentals have Internet and WiFi, 44 have TV and/or cable and 2 have a pool or hot tub. Search properties from 5 vacation rental sites in Chestertown where the top providers in that area are HomeAway, Booking.com, and VacationRentals. There are 40 HomeAway rentals, 2 Booking.com short term rentals and 2 VacationRentals vacation rentals.

Popular Day Trips Near Chestertown

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