Chester Vacation Rentals

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Vacation Rentals in Chester

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 Schunnemunk State Park and Brotherhood Winery.

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Vernon Township NJ

$272 nightly

$307 total

Jul 28 - Jul 29

Total with taxes and fees

When you stay at this vacation home in Vernon, you'll be in the mountains, just steps from Mountain Creek Ski Resort and 14 minutes by foot from Mountain Creek Waterpark.

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.

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

New Windsor NY

With a stay at this vacation home in New Windsor, you'll be on a river, within a 10-minute drive of United States Military Academy and Hudson River.

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.

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.

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

Fishkill NY

$283 nightly

$327 total

Jul 29 - Jul 30

Total with taxes and fees

With a stay at this vacation home in Fishkill, you'll be within a 10-minute drive of SplashDown Beach and Northeast Regional Epilepsy Group.

Large Lake House Property Your Family And Friends Will Love Staying At!

Greenwood Lake NY

With a stay at this vacation home in Greenwood Lake, you'll be on a lake, just a 1-minute walk from Greenwood Lake and 8 minutes by foot from Lion's Field Park.

Lakefront Paradise Pool + Paddle Boats Sleeps 12

Monroe NY

$1,830 nightly

$2,070 total

Aug 5 - Aug 6

Total with taxes and fees

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

With a stay at this vacation home, you'll be centrally located in Beacon, within a 10-minute drive of SplashDown Beach and Mount Gulian Historic Site.

Private Mountain Creek Getaway!

Vernon Township NJ

$375 nightly

$423 total

Jul 30 - Jul 31

Total with taxes and fees

When you stay at this vacation home in Vernon, you'll be on a river, a 2-minute drive from Mountain Creek Ski Resort and 7 minutes from Mountain Creek Waterpark.

5 bdrm Victorian, built in 1881-With 21 rooms, on a hill on 4 VERY private acres

New Windsor NY

Located in New Windsor, this vacation home is within a 15-minute drive of United States Military Academy and SplashDown Beach.

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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.