Find Vacation Rentals in Chestertown

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Popular Chestertown Vacation Rentals

Find the perfect Chestertown vacation rental

House Chestertown
from $298 per night
House ∙ 8 guests ∙ 3 bedrooms

119 m² House

5.0
Outstanding(1 rating)
Chestertown, Chester, New York, United States
HomeToGo
Details
House Chestertown
from $535 per night
House ∙ 10 guests ∙ 7 bedrooms

264 m² House

4.4
Very good(36 ratings)
Chestertown, Chester, New York, United States
Vrbo
Details
House Chestertown
from $309 per night
House ∙ 8 guests ∙ 4 bedrooms

130 m² House

5.0
Outstanding(44 ratings)
Chestertown, Chester, New York, United States
Vrbo
Details
House Chestertown
from $462 per night
House ∙ 10 guests ∙ 6 bedrooms

264 m² House

4.4
Very good(36 ratings)
Chestertown, Chester, New York, United States
Vacasa
Details
House Chestertown
from $228 per night
8 guests ∙ 3 bedrooms

House

5.0
Outstanding(16 ratings)
Chestertown, Chester, New York, United States
Vrbo
Details
House Chestertown
from $301 per night
House ∙ 18 guests ∙ 6 bedrooms

372 m² House

4.2
Very good(49 ratings)
Chestertown, Chester, New York, United States
Vrbo
Details
Lodge Chestertown
from $251 per night
Lodge ∙ 8 guests ∙ 4 bedrooms

186 m² Lodge

5.0
Outstanding(47 ratings)
Chestertown, Chester, New York, United States
Vrbo
Details
House Chestertown
from $123 per night
6 guests ∙ 3 bedrooms

House

5.0
Outstanding(20 ratings)
Chestertown, Chester, New York, United States
Vrbo
Details
House Chestertown
from $507 per night
House ∙ 9 guests ∙ 4 bedrooms

186 m² House

5.0
Outstanding(44 ratings)
Chestertown, Chester, New York, United States
Vrbo
Details
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Recommended Rentals With Pools

House  Chestertown
from $247 per night
2 guests ∙ 1 bedroom

House

4.7
Excellent(6 ratings)
Chestertown, Chester, New York, United States
Pool
Vrbo
Details
House  Chestertown
from $275 per night
2 guests ∙ 1 bedroom

House

Chestertown, Chester, New York, United States
Pool
Vio.com
Details
House  Chestertown
from $350 per night
6 guests ∙ 3 bedrooms

House

5.0
Outstanding(21 ratings)
Chestertown, Chester, New York, United States
Pool
Vrbo
Details
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Pet-Friendly Homes and Apartments

House  Chestertown
-12%
$222
from $205 per night
House ∙ 8 guests ∙ 3 bedrooms

149 m² House

4.9
Outstanding(20 ratings)
Chestertown, Chester, New York, United States
Pet-friendly
Vacasa
Details
Cabin  Chestertown
from $278 per night
Cabin ∙ 6 guests ∙ 2 bedrooms

74 m² Cabin

4.6
Excellent(29 ratings)
Chestertown, Chester, New York, United States
Pet-friendly
Vrbo
Details
Cottage  Chestertown
from $169 per night
Cottage ∙ 5 guests ∙ 4 bedrooms

68 m² Cottage

4.0
Very good(4 ratings)
Chestertown, Chester, New York, United States
Pet-friendly
Vrbo
Details
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Vacation Homes With Terraces

Motel  Chestertown
from $220 per night
2 guests ∙ 1 bedroom

Motel

Chestertown, Chester, New York, United States
Balcony/Patio
Vio.com
Details
Chalet  Chestertown
from $384 per night
8 guests ∙ 3 bedrooms

Chalet

4.9
Outstanding(30 ratings)
Chestertown, Chester, New York, United States
Balcony/Patio
Vrbo
Details
House  Chestertown
from $548 per night
House ∙ 11 guests ∙ 6 bedrooms

260 m² House

4.7
Excellent(28 ratings)
Chestertown, Chester, New York, United States
Balcony/Patio
Vrbo
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 $121 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 103 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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