Chester Vacation Rentals
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Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
1 mi
50 rentals in Chester.
Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Secluded Spacious NY Getaway, 1 hour from NYC
Rental Home
6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Spacious Suite (1 hr to Manhattan)
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Summerville Getaway (30 min to Mt. Creek)
Rental Home
7 bedrooms
4 bathrooms
Sleeps 14
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6 bedroom colonial house
Rental Home
5 bedrooms
3 bathrooms
Sleeps 16
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One-of-a-kind 5BR cottage
Rental Home
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Incredible Ranch in the Woods - Peace and Luxury!
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
Rental Home
3 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Guesthouse 2 bedroom. 25min-West Point
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Country Bliss Oak forest - Relax into Nature Enjoying Year Round Wonders.
Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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AmazingViews:TheModernMountainHouse Spa+Heated Pool-1 Hour NYC
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront retreat with stellar water views just a short drive from West...
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Entire house with lake view on private road in rural setting
Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Lakefront/Legoland/West Point Retreat Under 1 Hour From NYC! Finished Game Room!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Historic Barn 2 Bedroom Apartment - 4 Minutes from Legoland NY / Racetrack View
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NATURE'S NIRVANA FOR FAMILY AND FRIEND
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Your Family Getaway - 1 Hour from NYC! Hudson Valley Charm w/ Modern Upgrades!
Rental Home
7 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Newly Renovated Gorgeous Home in Goshen
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Goshen Winter Getaway-HotTub-PetFriendly-Gym-FirePit
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Hudson Valley Getaway! Private Pool & Hot Tub! 1HR from NYC
Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Hay Loft in Historic Barn - 4 Minutes to Legoland / Racetrack Views
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury Huge 6Br Suits, 8.55Bth & Indoor Pool at Goshen Vicinity NY
Rental Home
6 bedrooms
9 bathrooms
Sleeps 10
Match: Sleeps
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Newly Renovated and Expanded Former Barn
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront Getaway w/ Mix of Cozy & Modern Touches
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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MAGNIFICENT CHILD-FRIENDLY HOME NEAR LEGOLAND!!!
Rental Home
3 bedrooms
4 bathrooms
Sleeps 22
Match: Sleeps
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Farmhouse... Updated
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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76 acres of peace and light in Hudson Valley
Rental Home
6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Warwick Hilltop Retreat
Rental Home
6 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Cozy Log Cabin in Hudson Valley
Rental Home
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Decked-Out Home: Hot Tub, Pool, Fire Pit & More!
Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Caren House Bed and Breafast
Private Room
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Hudson Valley ‘Rainbow House’ w/ Yard & Pool!
Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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NEW- Lake Lodge 35 miles to NYC w 2ooft LakeFront
Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Charming Swedish Cottage in the Woods - Washingtonville & West Point
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Hidden Creek at Monroe
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cozy Family Home Near West Point, Shopping, Skiing and Legoland
Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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NEW- 2 Side by Side MODERN Lake Houses - 35 miles from NY
Rental Home
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Elmwood Home - Pool, Firepit, 5 min to Legoland, located in beautiful Goshen, NY
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Unique Dutch Barn in the Hudson Valley
Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Gorgeous Log Cabin Getaway with Private Lake
Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Goshen Renovated 5 Bedroom Country Home
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Historic Hudson Valley Farm House
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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�Cozy Lakefront Getaway�
Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Mountain House Escape - 1 Hour from NYC
Rental Home
5 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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Secluded Contemporary Home on 6-Acre Property!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Awesome Country Retreat - 5BR - Private and Peaceful
Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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The Twin Lakes House - Lake view
Rental Home
7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Stunning, Private House in the Hills - Huge Pool!
Rental Home
5 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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The Goshen Getaways
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Frequently Asked Questions about Chester
- Yes, here are some popular vacation rentals in Chester that have a pool:
- Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
- Guesthouse 2 bedroom. 25min-West Point
- Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
- Yes, here are some popular vacation rentals in Chester that have internet access:
- Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
- Guesthouse 2 bedroom. 25min-West Point
- Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
- The best pet friendly rentals in Chester are:
- Guesthouse 2 bedroom. 25min-West Point
- One-of-a-kind 5BR cottage
- Incredible Ranch in the Woods - Peace and Luxury!
- Some of the most popular kid friendly rentals in Chester are:
- Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
- Guesthouse 2 bedroom. 25min-West Point
- Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard