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Holiday Rentals in Westchester County

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67 rentals in Westchester County.
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Lakeside Modern Farmhouse/Craftsman Chalet, holiday rental in Westchester County
Lakeside Modern Farmhouse/Craftsman Chalet, holiday rental in Westchester County
Lakeside Modern Farmhouse/Craftsman Chalet, holiday rental in Westchester County

Lakeside Modern Farmhouse/Craftsman Chalet

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Luxury 2bd⭐ Comfort+Style ⭐45min to NYC,Great Food, holiday rental in Westchester County
Luxury 2bd⭐ Comfort+Style ⭐45min to NYC,Great Food, holiday rental in Westchester County
Luxury 2bd⭐ Comfort+Style ⭐45min to NYC,Great Food, holiday rental in Westchester County

Luxury 2bd⭐ Comfort+Style ⭐45min to NYC,Great Food

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Luxury home with great access that sleeps up to twelve. More photos available., holiday rental in Westchester County
Luxury home with great access that sleeps up to twelve. More photos available., holiday rental in Westchester County
Luxury home with great access that sleeps up to twelve. More photos available., holiday rental in Westchester County

Luxury home with great access that sleeps up to twelve. More photos available.

Holiday Rental House
6 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Over Sized Colonial on Private Road., holiday rental in Westchester County
Over Sized Colonial on Private Road., holiday rental in Westchester County
Over Sized Colonial on Private Road., holiday rental in Westchester County

Over Sized Colonial on Private Road.

Holiday Rental House
6 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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The Perfect Studio Getaway, holiday rental in Westchester County
The Perfect Studio Getaway, holiday rental in Westchester County
The Perfect Studio Getaway, holiday rental in Westchester County

The Perfect Studio Getaway

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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HUGE BEAUTIFUL 3 BEDROOMS 2 BATH. APARTMENT WITH ATTIC - 30 MIN TO NYC BY TRAIN, holiday rental in Westchester County
HUGE BEAUTIFUL 3 BEDROOMS 2 BATH. APARTMENT WITH ATTIC - 30 MIN TO NYC BY TRAIN, holiday rental in Westchester County
HUGE BEAUTIFUL 3 BEDROOMS 2 BATH. APARTMENT WITH ATTIC - 30 MIN TO NYC BY TRAIN, holiday rental in Westchester County

HUGE BEAUTIFUL 3 BEDROOMS 2 BATH. APARTMENT WITH ATTIC - 30 MIN TO NYC BY TRAIN

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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Fabulous Rye Beach Cottage, holiday rental in Westchester County
Fabulous Rye Beach Cottage, holiday rental in Westchester County
Fabulous Rye Beach Cottage, holiday rental in Westchester County

Fabulous Rye Beach Cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Holiday cozy country cottage!, holiday rental in Westchester County
Holiday cozy country cottage!, holiday rental in Westchester County
Holiday cozy country cottage!, holiday rental in Westchester County

Holiday cozy country cottage!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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5-Br 3-bath Skylit Home on 3 Forested Acres, holiday rental in Westchester County
5-Br 3-bath Skylit Home on 3 Forested Acres, holiday rental in Westchester County
5-Br 3-bath Skylit Home on 3 Forested Acres, holiday rental in Westchester County

5-Br 3-bath Skylit Home on 3 Forested Acres

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Maison au bord du lac Waccabuc, 50 miles de NYC, South Salem, 4 miles du Chateau, holiday rental in Westchester County
Maison au bord du lac Waccabuc, 50 miles de NYC, South Salem, 4 miles du Chateau, holiday rental in Westchester County
Maison au bord du lac Waccabuc, 50 miles de NYC, South Salem, 4 miles du Chateau, holiday rental in Westchester County

Maison au bord du lac Waccabuc, 50 miles de NYC, South Salem, 4 miles du Chateau

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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The beautiful HillSide Cottage awaits you!  Great location and close to NY city!, holiday rental in Westchester County
The beautiful HillSide Cottage awaits you!  Great location and close to NY city!, holiday rental in Westchester County
The beautiful HillSide Cottage awaits you!  Great location and close to NY city!, holiday rental in Westchester County

The beautiful HillSide Cottage awaits you! Great location and close to NY city!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Neighbor's House -- Welcome!, holiday rental in Westchester County
Neighbor's House -- Welcome!, holiday rental in Westchester County
Neighbor's House -- Welcome!, holiday rental in Westchester County

Neighbor's House -- Welcome!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Modern Hudson Valley Farmhouse just 50 min from NYC, holiday rental in Westchester County
Modern Hudson Valley Farmhouse just 50 min from NYC, holiday rental in Westchester County
Modern Hudson Valley Farmhouse just 50 min from NYC, holiday rental in Westchester County

Modern Hudson Valley Farmhouse just 50 min from NYC

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Bright & Airy Apartment w/ Balcony ~20 Mi to NYC!, holiday rental in Westchester County
Bright & Airy Apartment w/ Balcony ~20 Mi to NYC!, holiday rental in Westchester County
Bright & Airy Apartment w/ Balcony ~20 Mi to NYC!, holiday rental in Westchester County

Bright & Airy Apartment w/ Balcony ~20 Mi to NYC!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Marvelous 2 Bedroom apartment, holiday rental in Westchester County
Marvelous 2 Bedroom apartment, holiday rental in Westchester County
Marvelous 2 Bedroom apartment, holiday rental in Westchester County

Marvelous 2 Bedroom apartment

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Valhalla Sky 1 Queenn Rm, holiday rental in Westchester County
Valhalla Sky 1 Queenn Rm, holiday rental in Westchester County
Valhalla Sky 1 Queenn Rm, holiday rental in Westchester County

Valhalla Sky 1 Queenn Rm

Private Room
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Tiny House Close to NYC on Hudson River, holiday rental in Westchester County
Tiny House Close to NYC on Hudson River, holiday rental in Westchester County
Tiny House Close to NYC on Hudson River, holiday rental in Westchester County

Tiny House Close to NYC on Hudson River

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Modern,CloseToMetro/City,4BR/2BA, Free Parking- 35 minutes to NYC, holiday rental in Westchester County
Modern,CloseToMetro/City,4BR/2BA, Free Parking- 35 minutes to NYC, holiday rental in Westchester County
Modern,CloseToMetro/City,4BR/2BA, Free Parking- 35 minutes to NYC, holiday rental in Westchester County

Modern,CloseToMetro/City,4BR/2BA, Free Parking- 35 minutes to NYC

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Charming Rye Colonial Walk to Town & Train, holiday rental in Westchester County
Charming Rye Colonial Walk to Town & Train, holiday rental in Westchester County
Charming Rye Colonial Walk to Town & Train, holiday rental in Westchester County

Charming Rye Colonial Walk to Town & Train

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Private Double Room in House near NY Medical School, holiday rental in Westchester County
Private Double Room in House near NY Medical School, holiday rental in Westchester County
Private Double Room in House near NY Medical School, holiday rental in Westchester County

Private Double Room in House near NY Medical School

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Sunrise Waterfront House, holiday rental in Westchester County
Sunrise Waterfront House, holiday rental in Westchester County
Sunrise Waterfront House, holiday rental in Westchester County

Sunrise Waterfront House

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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PRIVATE 2 BEDROOM APARTMENT, holiday rental in Westchester County
PRIVATE 2 BEDROOM APARTMENT, holiday rental in Westchester County
PRIVATE 2 BEDROOM APARTMENT, holiday rental in Westchester County

PRIVATE 2 BEDROOM APARTMENT

Condo/Apartment in Wakefield
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Modern Comfy Studio 30 min from Manhattan - Yonkers NY, holiday rental in Westchester County
Modern Comfy Studio 30 min from Manhattan - Yonkers NY, holiday rental in Westchester County
Modern Comfy Studio 30 min from Manhattan - Yonkers NY, holiday rental in Westchester County

Modern Comfy Studio 30 min from Manhattan - Yonkers NY

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Charming Rye Colonial Walk to Town & Train, holiday rental in Westchester County
Charming Rye Colonial Walk to Town & Train, holiday rental in Westchester County
Charming Rye Colonial Walk to Town & Train, holiday rental in Westchester County

Charming Rye Colonial Walk to Town & Train

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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5 Bedroom House Near Manhattan & Connecticut, holiday rental in Westchester County
5 Bedroom House Near Manhattan & Connecticut, holiday rental in Westchester County
5 Bedroom House Near Manhattan & Connecticut, holiday rental in Westchester County

5 Bedroom House Near Manhattan & Connecticut

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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La Casita Bonita Near NYC, holiday rental in Westchester County
La Casita Bonita Near NYC, holiday rental in Westchester County
La Casita Bonita Near NYC, holiday rental in Westchester County

La Casita Bonita Near NYC

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Westchester Castle | 49 Min to NYC | Historic | Spacious | Pool Table, holiday rental in Westchester County
Westchester Castle | 49 Min to NYC | Historic | Spacious | Pool Table, holiday rental in Westchester County
Westchester Castle | 49 Min to NYC | Historic | Spacious | Pool Table, holiday rental in Westchester County

Westchester Castle | 49 Min to NYC | Historic | Spacious | Pool Table

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
More info
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Larchmont Manor: Walking Distance To Train, Town and Schools 30 Minutes from NYC, holiday rental in Westchester County
Larchmont Manor: Walking Distance To Train, Town and Schools 30 Minutes from NYC, holiday rental in Westchester County
Larchmont Manor: Walking Distance To Train, Town and Schools 30 Minutes from NYC, holiday rental in Westchester County

Larchmont Manor: Walking Distance To Train, Town and Schools 30 Minutes from NYC

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
More info
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Dramatic Family Home 30 Minutes From NYC, holiday rental in Westchester County
Dramatic Family Home 30 Minutes From NYC, holiday rental in Westchester County
Dramatic Family Home 30 Minutes From NYC, holiday rental in Westchester County

Dramatic Family Home 30 Minutes From NYC

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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private loft bedroom with bath, holiday rental in Westchester County
private loft bedroom with bath, holiday rental in Westchester County
private loft bedroom with bath, holiday rental in Westchester County

private loft bedroom with bath

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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A new 1BR close to White Plains Train Station, holiday rental in Westchester County
A new 1BR close to White Plains Train Station, holiday rental in Westchester County
A new 1BR close to White Plains Train Station, holiday rental in Westchester County

A new 1BR close to White Plains Train Station

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Quaint Yonkers Condo - 1 Block to Hudson River!, holiday rental in Westchester County
Quaint Yonkers Condo - 1 Block to Hudson River!, holiday rental in Westchester County
Quaint Yonkers Condo - 1 Block to Hudson River!, holiday rental in Westchester County

Quaint Yonkers Condo - 1 Block to Hudson River!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Tranquil Country Contemporary, holiday rental in Westchester County
Tranquil Country Contemporary, holiday rental in Westchester County
Tranquil Country Contemporary, holiday rental in Westchester County

Tranquil Country Contemporary

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Quiet Comfort by the Big Apple - Une Oasis Tout Pres De New York, holiday rental in Westchester County
Quiet Comfort by the Big Apple - Une Oasis Tout Pres De New York, holiday rental in Westchester County
Quiet Comfort by the Big Apple - Une Oasis Tout Pres De New York, holiday rental in Westchester County

Quiet Comfort by the Big Apple - Une Oasis Tout Pres De New York

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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A dream summer rental 30 miles from New York City in picturesque Bedford, NY!, holiday rental in Westchester County
A dream summer rental 30 miles from New York City in picturesque Bedford, NY!, holiday rental in Westchester County
A dream summer rental 30 miles from New York City in picturesque Bedford, NY!, holiday rental in Westchester County

A dream summer rental 30 miles from New York City in picturesque Bedford, NY!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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Mid Century Modern Hilltop Retreat, holiday rental in Westchester County
Mid Century Modern Hilltop Retreat, holiday rental in Westchester County
Mid Century Modern Hilltop Retreat, holiday rental in Westchester County

Mid Century Modern Hilltop Retreat

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
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Beautiful property one minute from Winged Foot golf course, holiday rental in Westchester County
Beautiful property one minute from Winged Foot golf course, holiday rental in Westchester County
Beautiful property one minute from Winged Foot golf course, holiday rental in Westchester County

Beautiful property one minute from Winged Foot golf course

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
More info
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4 BRs, Less than 1 mile to Winged Foot Golf Club, holiday rental in Westchester County
4 BRs, Less than 1 mile to Winged Foot Golf Club, holiday rental in Westchester County
4 BRs, Less than 1 mile to Winged Foot Golf Club, holiday rental in Westchester County

4 BRs, Less than 1 mile to Winged Foot Golf Club

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beautiful Private House; Golf, Hike, Fish, Swim, Relax, holiday rental in Westchester County
Beautiful Private House; Golf, Hike, Fish, Swim, Relax, holiday rental in Westchester County
Beautiful Private House; Golf, Hike, Fish, Swim, Relax, holiday rental in Westchester County

Beautiful Private House; Golf, Hike, Fish, Swim, Relax

Holiday Rental House
2 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
More info
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Private Secluded Estate Home with Pool and Waterfall in beautiful community, holiday rental in Westchester County
Private Secluded Estate Home with Pool and Waterfall in beautiful community, holiday rental in Westchester County
Private Secluded Estate Home with Pool and Waterfall in beautiful community, holiday rental in Westchester County

Private Secluded Estate Home with Pool and Waterfall in beautiful community

Holiday Rental House
4 bedrooms
7 bathrooms
Sleeps 6
Match: Sleeps
More info
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One of a Kind Cotswold Summer Retreat on 18 Secluded Acres, holiday rental in Westchester County
One of a Kind Cotswold Summer Retreat on 18 Secluded Acres, holiday rental in Westchester County
One of a Kind Cotswold Summer Retreat on 18 Secluded Acres, holiday rental in Westchester County

One of a Kind Cotswold Summer Retreat on 18 Secluded Acres

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Habitación moderna amplia y acogedora, holiday rental in Westchester County
Habitación moderna amplia y acogedora, holiday rental in Westchester County
Habitación moderna amplia y acogedora, holiday rental in Westchester County

Habitación moderna amplia y acogedora

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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The Cozy Family Home, holiday rental in Westchester County
The Cozy Family Home, holiday rental in Westchester County
The Cozy Family Home, holiday rental in Westchester County

The Cozy Family Home

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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Perfect Home for 2020 U.S. Open at Winged Foot, holiday rental in Westchester County
Perfect Home for 2020 U.S. Open at Winged Foot, holiday rental in Westchester County
Perfect Home for 2020 U.S. Open at Winged Foot, holiday rental in Westchester County

Perfect Home for 2020 U.S. Open at Winged Foot

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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La Casita Bonita  near NYC, holiday rental in Westchester County
La Casita Bonita  near NYC, holiday rental in Westchester County
La Casita Bonita  near NYC, holiday rental in Westchester County

La Casita Bonita near NYC

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Gorgeous Westchester Home with Pool, Hot Tub, Steam Room & Tennis!, holiday rental in Westchester County
Gorgeous Westchester Home with Pool, Hot Tub, Steam Room & Tennis!, holiday rental in Westchester County
Gorgeous Westchester Home with Pool, Hot Tub, Steam Room & Tennis!, holiday rental in Westchester County

Gorgeous Westchester Home with Pool, Hot Tub, Steam Room & Tennis!

Holiday Rental House
8 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
More info
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Little studio with parking in  Yonkers safe location close to all, holiday rental in Westchester County
Little studio with parking in  Yonkers safe location close to all, holiday rental in Westchester County
Little studio with parking in  Yonkers safe location close to all, holiday rental in Westchester County

Little studio with parking in Yonkers safe location close to all

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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1870 Restored Victorian with Pool, sleeps 12, walking distance to train to NYC, holiday rental in Westchester County
1870 Restored Victorian with Pool, sleeps 12, walking distance to train to NYC, holiday rental in Westchester County
1870 Restored Victorian with Pool, sleeps 12, walking distance to train to NYC, holiday rental in Westchester County

1870 Restored Victorian with Pool, sleeps 12, walking distance to train to NYC

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Single Family Home 10 Min from US OPEN * Winged Foot, holiday rental in Westchester County
Single Family Home 10 Min from US OPEN * Winged Foot, holiday rental in Westchester County
Single Family Home 10 Min from US OPEN * Winged Foot, holiday rental in Westchester County

Single Family Home 10 Min from US OPEN * Winged Foot

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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LIVE ON A BEAUTIFUL LAKE one hour from New York City!, holiday rental in Westchester County
LIVE ON A BEAUTIFUL LAKE one hour from New York City!, holiday rental in Westchester County
LIVE ON A BEAUTIFUL LAKE one hour from New York City!, holiday rental in Westchester County

LIVE ON A BEAUTIFUL LAKE one hour from New York City!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Frequently Asked Questions about Westchester County