Chester Vacation Rentals
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Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 mi
48 rentals in Chester.
Charming Historic Farmhouse
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Peace and Privacy at 5 BDRM Villa Set on Wooded Lot
Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private fun
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Luxury in the Woods, Pool, Privacy and Peace
Rental Home
6 bedrooms
3 bathrooms
Sleeps 16
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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Guesthouse 2 bedroom. 25min-West Point
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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6 bedroom colonial house
Rental Home
5 bedrooms
3 bathrooms
Sleeps 16
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1,******* Mansion Affordable Luxury on 1.5 Acres surrounded by fun things to do!
Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
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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Secluded Spacious NY Getaway, 1 hour from NYC
Rental Home
6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
Rental Home
7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Dexluxe Vacay in Chester
Rental Home
8 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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The following properties within 20 miles of Chester match all your filters:
Awesome Country Retreat - 4BR - Private and Peaceful
Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
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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Spacious Family Oasis ~ Pool ~ GameRoom ~ Backyard
Rental Home
7 bedrooms
4 bathrooms
Sleeps 22
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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Historic Hudson Valley Farm House
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Unique Scenic home with king suite & hot tub
Rental Home
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Rental Home
6 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Cozy, Private Walton Lakefront Getaway 2B/2B Home
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Hay Loft in Historic Barn - 4 Minutes to Legoland / Racetrack Views
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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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Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Charming brick house surrounded lakes and the fresh air of the mountains
Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy Private Cottage near Woodbury Commons, Trails
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Historic 3-Bedroom 2-Full Baths Victorian Home Fully Furnished in Prime Location
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Hudson Valley Mid Century Bungalow 1 hr from NYC
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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The Great Goshen Getaway
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Relaxing New York Home w/ Boat Dock & Lake View!
Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Monthly Rental, In Warwick
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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NEW- Lake Home 35 miles to NYC w/ 2oo ft private west facing Lake Front
Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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TheGoshenGetawaysHeatedPoolHotTubPetFriendly
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Goshe Farmhouse Legoland NY
Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Upstate Bliss LAKE HOME - Relax into Nature Enjoying Year Round Wonders.
Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Sanctuary Amidst Natures Majesty
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
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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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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Spacious Home w/Pool/Hot Tub, Mins to Parks/Skiing
Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
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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Goshen Renovated 5 Bedroom Country Home
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
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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Luxurious & Tranquil ~ Pool ~ Fire Pit ~ Backyard!
Rental Home
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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The Sweet Spot: Oasis w/ In Ground Pool
Rental Home
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Lakefront/Legoland/West Point Retreat Under 1 Hour From NYC! Heated pool & Spa!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Incredible Ranch in the Woods - Lake View - Peace and Luxury!
Rental Home
7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Mountain House Escape - 1 Hour from NYC
Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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NEW-2 Side by Side Lake Homes - Sleep 17, pet friendly and 2 private docks.
Rental Home
7 bedrooms
4 bathrooms
Sleeps 17
Match: Sleeps
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Showing results 1-48 of 48
Frequently Asked Questions about Chester
- Yes, here are some popular vacation rentals in Chester that have a pool:
- Charming Historic Farmhouse
- Peace and Privacy at 5 BDRM Villa Set on Wooded Lot
- Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
- Yes, here are some popular vacation rentals in Chester that have internet access:
- Charming Historic Farmhouse
- Peace and Privacy at 5 BDRM Villa Set on Wooded Lot
- Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
- Some of the most popular kid friendly rentals in Chester are:
- Charming Historic Farmhouse
- Peace and Privacy at 5 BDRM Villa Set on Wooded Lot
- Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
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