Find Vacation Rentals in Chestertown

We have 68 properties to choose from
Chestertown
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Chestertown
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Popular Chestertown Vacation Rentals

Find the perfect Chestertown vacation rental

House Chestertown
from $260 per night
House ∙ 8 guests ∙ 3 bedrooms
Chestertown, Chester, New York, United States
Details
HomeToGo
Details
Details
House Chestertown
from $453 per night
House ∙ 10 guests ∙ 6 bedrooms
4.4
Very good (25 ratings)
Chestertown, Chester, New York, United States
Details
Vacasa
Details
Details
House Chestertown
from $460 per night
House ∙ 18 guests ∙ 6 bedrooms
4.1
Very good (48 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
Details
Details
House Chestertown
from $349 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (41 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
Details
Details
House Chestertown
from $492 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (39 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
Details
Details
House Chestertown
from $278 per night
House ∙ 10 guests ∙ 3 bedrooms
4.7
Excellent (24 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
Details
Details
Cabin Chestertown
from $248 per night
Cabin ∙ 6 guests ∙ 2 bedrooms
4.6
Excellent (29 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
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Details
Lodge Chestertown
from $258 per night
Lodge ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (40 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
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Details
House Chestertown
from $234 per night
House ∙ 8 guests ∙ 2 bedrooms
5.0
Outstanding (6 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
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Recommended Rentals With Pools

House  Chestertown
from $655 per night
House ∙ 14 guests ∙ 4 bedrooms
5.0
Outstanding (1 rating)
Chestertown, Chester, New York, United States
Pool
Details
Vrbo
Details
Details
House  Chestertown
from $296 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (21 ratings)
Chestertown, Chester, New York, United States
Pool
Details
Vrbo
Details
Details
House  Chestertown
from $348 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (21 ratings)
Chestertown, Chester, New York, United States
Pool
Details
Vrbo
Details
Details
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Pet-Friendly Homes and Apartments

House  Chestertown
from $253 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (9 ratings)
Chestertown, Chester, New York, United States
Pet-friendly
Details
Vrbo
Details
Details
House  Chestertown
from $192 per night
House ∙ 8 guests ∙ 2 bedrooms
5.0
Outstanding (24 ratings)
Chestertown, Chester, New York, United States
Pet-friendly
Details
Vrbo
Details
Details
Cottage  Chestertown
from $194 per night
Cottage ∙ 5 guests ∙ 3 bedrooms
Chestertown, Chester, New York, United States
Pet-friendly
Details
Vrbo
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Details
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Best vacation rentals with a balcony

Cabin  Chestertown
from $351 per night
Cabin ∙ 6 guests ∙ 3 bedrooms
4.8
Outstanding (23 ratings)
Chestertown, Chester, New York, United States
Balcony
Details
Vrbo
Details
Details
House  Chestertown
from $238 per night
House ∙ 10 guests ∙ 3 bedrooms
4.5
Excellent
Chestertown, Chester, New York, United States
Balcony
Details
Vacasa
Details
Details
Apartment  Chestertown
from $246 per night
Apartment ∙ 16 guests ∙ 4 bedrooms
4.5
Excellent (7 ratings)
Chestertown, Chester, New York, United States
Balcony
Details
Vrbo
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 $160 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 68 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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