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Chester Holiday Rentals

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50 rentals in Chester.
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Luxury Apt Sugar Loaf, Near Warwick, holiday rental in Chester

Luxury Apt Sugar Loaf, Near Warwick

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View, holiday rental in Chester

Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

2 bedrooms
2 bathrooms
Sleeps 6
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Cozy Lake House Near Mountain Creek & Warwick, NY - Under 5 miles to the Slopes!, holiday rental in Chester

Cozy Lake House Near Mountain Creek & Warwick, NY - Under 5 miles to the Slopes!

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Lakefront New York City Getaway Only One Hour Away in northern New Jersey, holiday rental in Chester

Lakefront New York City Getaway Only One Hour Away in northern New Jersey

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Private rural Timberframe House on 5 wooded acres in Mountainville, NY., holiday rental in Chester

Private rural Timberframe House on 5 wooded acres in Mountainville, NY.

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Private AT Historic Mountain Home... Where Serenity awaits... Right off the AT!, holiday rental in Chester

Private AT Historic Mountain Home... Where Serenity awaits... Right off the AT!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Orchard Hill + SANITIZED -1hr NYC, Remote, Corporate Retreats, Spacious, Private, holiday rental in Chester

Orchard Hill + SANITIZED -1hr NYC, Remote, Corporate Retreats, Spacious, Private

8 bedrooms
5 bathrooms
Sleeps 25
Match: Sleeps
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Modern Lake house - Private dock  - 35 miles Out of NYC, holiday rental in Chester

Modern Lake house - Private dock - 35 miles Out of NYC

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Cozy Cottage minutes to West Point, holiday rental in Chester

Cozy Cottage minutes to West Point

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Farmhouse In Heart Of 590 Acres Of Preserved Farmland, holiday rental in Chester

Farmhouse In Heart Of 590 Acres Of Preserved Farmland

3 bedrooms
2 bathrooms
Sleeps 6
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Luxurious Sophisticated Get away for large family or groups, holiday rental in Chester

Luxurious Sophisticated Get away for large family or groups

5 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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Rocky Point- Aboslutely the BEST Location on Greenwood Lake! 1 hour from NYC., holiday rental in Chester

Rocky Point- Aboslutely the BEST Location on Greenwood Lake! 1 hour from NYC.

3 bedrooms
2 bathrooms
Sleeps 8
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Modern Cabin Just Over An Hour From NYC!, holiday rental in Chester

Modern Cabin Just Over An Hour From NYC!

3 bedrooms
2 bathrooms
Sleeps 8
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Cosy lakefront cottage in Hudson Valley, holiday rental in Chester

Cosy lakefront cottage in Hudson Valley

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Fabulous 2nd Floor private apartment in Warwick Village, great space., holiday rental in Chester

Fabulous 2nd Floor private apartment in Warwick Village, great space.

4 bedrooms
1 bathroom
Sleeps 6
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West Point - Bear Mountain - Woodbury Commons, holiday rental in Chester

West Point - Bear Mountain - Woodbury Commons

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Historic Barn 2 Bedroom Apartment - Racetrack View, holiday rental in Chester

Historic Barn 2 Bedroom Apartment - Racetrack View

2 bedrooms
1 bathroom
Sleeps 6
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Apples, foliage, wineries, farms., holiday rental in Chester

Apples, foliage, wineries, farms.

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Pine Valley - #48 - Mountain Front-Skiing-Hiking-Wineries-WiFi-50 miles from NYC, holiday rental in Chester

Pine Valley - #48 - Mountain Front-Skiing-Hiking-Wineries-WiFi-50 miles from NYC

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Barrett's Barn House, Fabulous in Warwick, NY, holiday rental in Chester

Barrett's Barn House, Fabulous in Warwick, NY

3 bedrooms
3 bathrooms
Sleeps 6
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50 Mins from  Manhattan River view, holiday rental in Chester

50 Mins from Manhattan River view

5 bedrooms
3 bathrooms
Sleeps 17
Match: Sleeps
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Storm King Lodge is a country retreat ready for you., holiday rental in Chester

Storm King Lodge is a country retreat ready for you.

4 bedrooms
4 bathrooms
Sleeps 10
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Stay at Sparrow House: A Cozy, Waterfront Retreat in the Hudson Valley, holiday rental in Chester

Stay at Sparrow House: A Cozy, Waterfront Retreat in the Hudson Valley

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Colonial Style 'Warwick Retreat' - 1 Hour to NYC!, holiday rental in Chester

Colonial Style 'Warwick Retreat' - 1 Hour to NYC!

4 bedrooms
3 bathrooms
Sleeps 10
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Caren House Bed and Breafast, holiday rental in Chester

Caren House Bed and Breafast

3 bedrooms
3 bathrooms
Sleeps 6
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Cozy Lake Front House w. Pool near Storm King and West Point, holiday rental in Chester

Cozy Lake Front House w. Pool near Storm King and West Point

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Wawayanda House on 62 Acres - Multiple Fireplaces!, holiday rental in Chester

Wawayanda House on 62 Acres - Multiple Fireplaces!

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Cottage at Millpond Falls - Warwick NY B&B, holiday rental in Chester

The Cottage at Millpond Falls - Warwick NY B&B

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Guests state the home is charming. New central air conditioning., holiday rental in Chester

Guests state the home is charming. New central air conditioning.

1 bedroom
1 bathroom
Sleeps 4
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Tentrr Signature Site - Camp Coal Tree, holiday rental in Chester

Tentrr Signature Site - Camp Coal Tree

1 bedroom
1 bathroom
Sleeps 4
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Warwick NY The Davis House, holiday rental in Chester

Warwick NY The Davis House

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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A Destination for All Seasons, holiday rental in Chester

A Destination for All Seasons

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Two Fields Farm   Close to NYC with beautiful pond, holiday rental in Chester

Tentrr Signature Site - Two Fields Farm Close to NYC with beautiful pond

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Historic Hudson Valley Riverside Hemp Farm, holiday rental in Chester

Tentrr Signature Site - Historic Hudson Valley Riverside Hemp Farm

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Twin Ponds on the FARM, holiday rental in Chester

Tentrr Signature Site - Twin Ponds on the FARM

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful house, Woodbury comns SKI NYC 55 Miles

0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
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NEW! Dtwn Goshen Escape: 1 Block to Historic Track, holiday rental in Chester

NEW! Dtwn Goshen Escape: 1 Block to Historic Track

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Dtwn Goshen Retreat: 29 Mi to Holiday Mtn Ski, holiday rental in Chester

NEW! Dtwn Goshen Retreat: 29 Mi to Holiday Mtn Ski

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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NEW! Romantic Goshen Getaway: Wineries + Shopping!, holiday rental in Chester

NEW! Romantic Goshen Getaway: Wineries + Shopping!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Tentrr State Park Site - NY Harriman State Park - Old Sebago Beach at Lake, holiday rental in Chester

Tentrr State Park Site - NY Harriman State Park - Old Sebago Beach at Lake

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr State Park Site - NY Harriman State Park - Midway at Silver Mine Lake, holiday rental in Chester

Tentrr State Park Site - NY Harriman State Park - Midway at Silver Mine Lake

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr State Park Site - NY Harriman State Park - Tucked Away at Silver Mine, holiday rental in Chester

Tentrr State Park Site - NY Harriman State Park - Tucked Away at Silver Mine

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr State Park Site - NY Harriman State Park - Fenced Field at Lake Sebago, holiday rental in Chester

Tentrr State Park Site - NY Harriman State Park - Fenced Field at Lake Sebago

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr State Park Site - NY Harriman State Park - Field of Five H for Large, holiday rental in Chester

Tentrr State Park Site - NY Harriman State Park - Field of Five H for Large

1 bedroom
1 bathroom
Sleeps 20
Match: Sleeps
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Tentrr State Park Site - NY Harriman State Park - Water View at Lake Sebago, holiday rental in Chester

Tentrr State Park Site - NY Harriman State Park - Water View at Lake Sebago

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr State Park Site - NY Harriman State Park - Old Comfort Station at Lake, holiday rental in Chester

Tentrr State Park Site - NY Harriman State Park - Old Comfort Station at Lake

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr State Park Site - NY Harriman State Park - Beaver Dam Silver Mine Lake, holiday rental in Chester

Tentrr State Park Site - NY Harriman State Park - Beaver Dam Silver Mine Lake

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Heavens Landing, holiday rental in Chester

Tentrr Signature Site - Heavens Landing

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Pastoral Paradise on 42-Acre Farm Close to NYC, holiday rental in Chester

Tentrr Signature Site - Pastoral Paradise on 42-Acre Farm Close to NYC

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Contemporary Home Style Getaway in Slate Hill NY, holiday rental in Chester

Contemporary Home Style Getaway in Slate Hill NY

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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