Holiday Homes in Chester
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48 rentals in Chester.
Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
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Private fun
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious Suite (1 hr to Manhattan)
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Guesthouse 2 bedroom. 25min-West Point
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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6 bedroom colonial house
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Millionare Mansion w/ Lrg Hot Tub on 1.5 Acres - fun activities all around!
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Secluded Spacious NY Getaway, 1 hour from NYC
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Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
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Comfortable 5BD Near Legoland Bear Mtn, West Point, Wineries, Woodbury Common
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Elegant Home w/7BRs, Game Room, Luxury Yard, Pool
Holiday Rental House
7 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Very Private Large Home on 22 Acres with Outdoor Kitchen
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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The following properties within 32 kms of Chester match all your filters:
Renovated House w/Hot Tub, Deck, Grill & Fire Pit
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Amazing Home Near West Point, Shopping, Skiing and Legoland
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Historic Hudson Valley Farm House
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Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
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Cozy, Private Walton Lakefront Getaway 2B/2B Home
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Hay Loft in Historic Barn - 4 Minutes to Legoland / Racetrack Views
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Historic Barn 2 Bedroom Apartment - 4 Minutes from Legoland NY / Racetrack View
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Goshen apartment located
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Charming house surrounded lakes and the fresh air of the mountains
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Historic 3-Bedroom 2-Full Baths Victorian Home Fully Furnished in Prime Location
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Hudson Valley Mid Century Monroe Bungalow -1 hr from NYC - Gourmet Kitchen
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The Goshen House - close to downtown with hot tub
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Relaxing New York Home w/ Boat Dock & Lake View!
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NEW- Lake Home 35 miles to NYC w/ 2oo ft private west facing Lake Front
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Goshe Farmhouse Legoland NY
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Upstate Bliss LAKE HOME - Relax into Nature Enjoying Year Round Wonders.
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Sanctuary Amidst Natures Majesty
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Lakefront retreat with stellar water views just a short drive from West...
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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76 acres of peace and light in Hudson Valley
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New 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
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Unique Dutch Barn in the Hudson Valley
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Luxurious & Tranquil ~ Pool ~ Fire Pit ~ Backyard!
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The Sweet Spot: Fun-Filled Fall Getaway
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Lakefront/Legoland/Mt. Peter Retreat Under 1 Hour From NYC! Heated pool & Spa!
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NEW-2 Side by Side Lake Homes - Sleep 17, pet friendly and 2 private docks.
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Spacious Smart Home Retreat on 14 Acres of Nature
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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The Cozy Goshen Home, 5mins from LEGOLAND and near skiing!
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Spectacular ~10k sqft Mansion w/Pool&Tennis
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Large 5-bedroom home on 3 acres with heated pool and billiard room
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons
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Lakeside Haven - Ultimate Relaxation Spot
Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.
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Modern minimalist home in the forest with hot tub
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Large Three bedroom apartment, Main St., Goshen
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Awesome Country Retreat - 4BR - Private & Peaceful
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Luxury 3-bedroom fully renovated house in Goshen with brand new furniture.
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Carriage House Apartment Close to Legoland NY
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Showing results 1-48 of 48
Frequently Asked Questions about Chester
- Yes, here are some popular holiday rentals in Chester that have a pool:
- Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
- Private fun
- Spacious Suite (1 hr to Manhattan)
- Yes, here are some popular holiday rentals in Chester that have internet access:
- Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
- Private fun
- Spacious Suite (1 hr to Manhattan)
- Some of the most popular kid friendly rentals in Chester are:
- Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
- Private fun
- Guesthouse 2 bedroom. 25min-West Point
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