Chester Vacation Rentals

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Vacation Rentals in Chester

Spacious 7BR Villa on 14 Acres w/ Indoor Pool

Washingtonville NY

Located in Blooming Grove, this vacation home is within a 10-minute drive of Brotherhood Winery and Schunnemunk State Park.

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

Wallkill NY

With a stay at this vacation home in Wallkill, you'll be within a 15-minute drive of Tuthilltown Spirits and Jenkinstown Day Spa.

Greenwood Lake Lakefront Luxury

Hewitt NJ

When you stay at this vacation home in West Milford, you'll be on the waterfront, within a 5-minute walk of Greenwood Lake and Long Pond Ironworks State Park.

Cozy Cabin with Sauna & Firepit!

Monroe NY

With a stay at this vacation home in Monroe, you'll be within a 15-minute drive of Brotherhood Winery and Museum Village.

Lakefront Paradise Pool + Paddle Boats Sleeps 12

Monroe NY

With a stay at this vacation home in Monroe, you'll be within a 15-minute drive of Woodbury Common Premium Outlets and LEGOLAND® New York.

Beacon,Hudson Valley, 4bedroom 2bath, Sleeps 7, Pool, Hot Tub, Wifi,1.5m to town

Beacon NY

A stay at this vacation home places you in the heart of Beacon, within a 5-minute drive of Mount Gulian Historic Site and Hudson River.

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Fishkill NY

$278 nightly

$321 total

Jun 15 - Jun 16

Total with taxes and fees

Located in Fishkill, this vacation home is a 4-minute drive from Blodgett Memorial Library and 6 minutes from SplashDown Beach.

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Newburgh NY

When you stay at this vacation home in Newburgh, you'll be on the waterfront, within a 5-minute drive of Town of Newburgh Little League and Ice Time Sports Complex.

Kitchen

Air conditioning

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Newburgh NY

When you stay at this vacation home in Newburgh, you'll be on the waterfront, within a 5-minute drive of Town of Newburgh Little League and Ice Time Sports Complex.

Modern Farmhouse on pristine private 12 Acres

Wallkill NY

Located in Wallkill, this vacation home is in the mountains, within a 15-minute drive of Minnewaska State Park and Whitecliff Vineyard.

Peekskill Carriage House Downtown Studio

Peekskill NY

With a stay at this vacation home in Peekskill, you'll be within a 15-minute drive of United States Military Academy and Paramount Hudson Valley Theater.

Cozy 1920’s home in the heart of Pine Bush

Pine Bush NY

A stay at this vacation home places you in the heart of Pine Bush, a 3-minute drive from Brimstone Hill Winery and 9 minutes from Angry Orchard.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.