Find Vacation Rentals in Chestertown

We have 98 properties to choose from
Anytime
1 guest
Anytime
1 guest

Popular Chestertown Vacation Rentals

Find the perfect Chestertown vacation rental

House Chestertown
from $235 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding(16 ratings)
Chestertown, Chester, New York, United States
Vrbo
Details
House Chestertown
from $312 per night
House ∙ 18 guests ∙ 6 bedrooms
4.2
Very good(49 ratings)
Chestertown, Chester, New York, United States
Vrbo
Details
Lodge Chestertown
from $250 per night
Lodge ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(47 ratings)
Chestertown, Chester, New York, United States
Vrbo
Details
House Chestertown
from $118 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(20 ratings)
Chestertown, Chester, New York, United States
Vrbo
Details
House Chestertown
from $481 per night
House ∙ 9 guests ∙ 4 bedrooms
5.0
Outstanding(44 ratings)
Chestertown, Chester, New York, United States
Vrbo
Details
House Chestertown
from $403 per night
House ∙ 10 guests ∙ 4 bedrooms
4.9
Outstanding(65 ratings)
Chestertown, Chester, New York, United States
Vrbo
Details
House Chestertown
-12%
$248
from $234 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(44 ratings)
Chestertown, Chester, New York, United States
Vacasa
Details
House Chestertown
from $306 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(18 ratings)
Chestertown, Chester, New York, United States
Vrbo
Details
House Chestertown
from $727 per night
House ∙ 12 guests ∙ 7 bedrooms
5.0
Outstanding(12 ratings)
Chestertown, Chester, New York, United States
Vrbo
Details
Show more

Recommended Rentals With Pools

House  Chestertown
from $255 per night
House ∙ 2 guests ∙ 1 bedroom
4.7
Excellent(6 ratings)
Chestertown, Chester, New York, United States
Pool
Vrbo
Details
House  Chestertown
from $277 per night
House ∙ 2 guests ∙ 1 bedroom
Chestertown, Chester, New York, United States
Pool
Vio.com
Details
House  Chestertown
from $374 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(21 ratings)
Chestertown, Chester, New York, United States
Pool
Vrbo
Details
Show more

Pet-Friendly Homes and Apartments

House  Chestertown
-12%
$257
from $219 per night
House ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding(20 ratings)
Chestertown, Chester, New York, United States
Pet-friendly
Vacasa
Details
Cabin  Chestertown
from $249 per night
Cabin ∙ 6 guests ∙ 2 bedrooms
4.6
Excellent(29 ratings)
Chestertown, Chester, New York, United States
Pet-friendly
Vrbo
Details
Cottage  Chestertown
from $191 per night
Cottage ∙ 5 guests ∙ 4 bedrooms
4.0
Very good(4 ratings)
Chestertown, Chester, New York, United States
Pet-friendly
Vrbo
Details
Show more

Vacation Homes With Terraces

Motel  Chestertown
from $215 per night
Motel ∙ 2 guests ∙ 1 bedroom
Chestertown, Chester, New York, United States
Balcony/Patio
Vio.com
Details
Chalet  Chestertown
from $413 per night
Chalet ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding(30 ratings)
Chestertown, Chester, New York, United States
Balcony/Patio
Vrbo
Details
House  Chestertown
from $497 per night
House ∙ 11 guests ∙ 6 bedrooms
4.7
Excellent(28 ratings)
Chestertown, Chester, New York, United States
Balcony/Patio
Vrbo
Details
Show more

Frequently Asked Questions

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

Accommodation in Chestertown cost from $118 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 98 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

image-tag