Find Vacation Rentals in Chestertown

We have 232 properties to choose from
Chestertown
Anytime
Guests

Popular Chestertown Vacation Rentals

Find the perfect Chestertown vacation rental

Lodge Chestertown
$277 per night
Lodge ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (5 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
Details
Details
Cabin Chestertown
$157 per night
Cabin ∙ 4 guests ∙ 1 bedroom
4.8
"Excellent" (33 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
Details
Details
Cabin Chestertown
$174 per night
Cabin ∙ 2 guests ∙ 1 bedroom
4.7
"Outstanding" (25 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
Details
Details
House Chestertown
$177 per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
"Excellent" (1 rating)
Chestertown, Chester, New York, United States
Details
Vrbo
Details
Details
House Chestertown
$362 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
"Excellent" (1 rating)
Chestertown, Chester, New York, United States
Details
Vrbo
Details
Details
House Chestertown
$307 per night
House ∙ 10 guests ∙ 5 bedrooms
4.7
"Outstanding" (142 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
Details
Details
House Chestertown
$370 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (1 rating)
Chestertown, Chester, New York, United States
Details
Vrbo
Details
Details
House Chestertown
$302 per night
House ∙ 8 guests ∙ 4 bedrooms
4.9
"Excellent" (14 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
Details
Details
Cabin Chestertown
$261 per night
Cabin ∙ 4 guests ∙ 2 bedrooms
4.0
"Very good" (12 ratings)
Chestertown, Chester, New York, United States
Details
Vrbo
Details
Details
View more

Vacation rentals and apartments with air conditioning

House Air conditioning Chestertown
$347 per night
House ∙ 6 guests ∙ 3 bedrooms
4.9
"Excellent" (21 ratings)
Chestertown, Chester, New York, United States
Air conditioning
Details
Vrbo
Details
Details
House Air conditioning Chestertown
$166 per night
House ∙ 4 guests ∙ 1 bedroom
Chestertown, Chester, New York, United States
Air conditioning
Details
Vrbo
Details
Details
House Air conditioning Chestertown
$251 per night
House ∙ 2 guests ∙ 1 bedroom
4.7
"Outstanding" (6 ratings)
Chestertown, Chester, New York, United States
Air conditioning
Details
Vrbo
Details
Details
View more

Best vacation rentals with a balcony

House Balcony Chestertown
$288 per night
House ∙ 6 guests ∙ 4 bedrooms
4.0
"Very good" (2 ratings)
Chestertown, Chester, New York, United States
Balcony
Details
Vrbo
Details
Details
House Balcony Chestertown
$91 per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
"Excellent" (1 rating)
Chestertown, Chester, New York, United States
Balcony
Details
Expedia
Details
Details
House Balcony Chestertown
$328 per night
House ∙ 8 guests ∙ 4 bedrooms
4.6
"Outstanding" (7 ratings)
Chestertown, Chester, New York, United States
Balcony
Details
Expedia
Details
Details
View more

Cabins and Homes With Fireplaces

Cabin Fireplace Chestertown
$261 per night
Cabin ∙ 4 guests ∙ 2 bedrooms
4.7
"Outstanding" (23 ratings)
Chestertown, Chester, New York, United States
Fireplace
Details
Vrbo
Details
Details
House Fireplace Chestertown
$277 per night
House ∙ 4 guests ∙ 2 bedrooms
4.0
"Very good" (4 ratings)
Chestertown, Chester, New York, United States
Fireplace
Details
Vrbo
Details
Details
House Fireplace Chestertown
$1,309 per night
House ∙ 25 guests ∙ 11 bedrooms
Chestertown, Chester, New York, United States
Fireplace
Details
Vrbo
Details
Details
View more

Frequently Asked Questions

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

Accommodation in Chestertown cost from $91 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 232 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