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Vacation rentals in Chester
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Chester
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chester vacation rentals
Other great vacation rentals in Chester
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Guest favorite
Cottage in Middletown
4.96 out of 5 average rating, 55 reviews⌂ Backyard Porch ⌂ Cozy Getaway ⌂ Catskills Hikes
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Guest favorite
Home in Chester
4.96 out of 5 average rating, 27 reviewsSugar Loaf Mountain Retreat with Hot Tub - 1hr/NYC
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Guest favorite
Home in Chester
5 out of 5 average rating, 17 reviewsRelaxing 5BD Close to Adventures Shops & Exploring
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Guest favorite
Rental unit in Goshen
4.92 out of 5 average rating, 48 reviewsPrivate 1 bedroom apartment Village of Goshen
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Guest favorite
Home in Monroe
4.96 out of 5 average rating, 98 reviewsLakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!
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Guest favorite
Villa in New Hampton
5 out of 5 average rating, 32 reviewsLuxury School House W/ Heated Pool - 1 HR from NYC
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Guest favorite
Home in Monroe
4.91 out of 5 average rating, 23 reviews3 BDR Cottage (Hudson Valley Cottage)
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Guest favorite
Home in Warwick
5 out of 5 average rating, 8 reviewsClose to wineries, breweries, hikes, lake, shops!
Quick stats about vacation rentals in Chester
Total rentals
10 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
660 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
The Castle Fun Center, ShopRite of Chester Plaza, and NY
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