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Holiday Rentals in Ossining

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50 rentals in Ossining.
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The Westchester Palace- 6BR Mansion w/ King Bed + Pool Near NYC, holiday rental in Ossining

The Westchester Palace- 6BR Mansion w/ King Bed + Pool Near NYC

5 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
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Country getaway with spectacular pond and mountain views, holiday rental in Ossining

Country getaway with spectacular pond and mountain views

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Built in 2018 3BR Lovely House near West Point, holiday rental in Ossining

Built in 2018 3BR Lovely House near West Point

3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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West Point - Bear Mountain - Woodbury Commons, holiday rental in Ossining

West Point - Bear Mountain - Woodbury Commons

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Twenty One ! Boutique Stay in Heart of Downtown, holiday rental in Ossining

Twenty One ! Boutique Stay in Heart of Downtown

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming and immaculate 3 br duplex!, holiday rental in Ossining

Charming and immaculate 3 br duplex!

3 bedrooms
1 bathroom
Sleeps 5
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Bear Mountain House., holiday rental in Ossining

Bear Mountain House.

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Our Rockbound Highland Home * 2 Blocks to West Point * 1/2 Block to Main St, holiday rental in Ossining

Our Rockbound Highland Home * 2 Blocks to West Point * 1/2 Block to Main St

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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The Perfect Studio Getaway

0 bedrooms
0 bathrooms
Sleeps 0
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Holiday cozy country cottage!, holiday rental in Ossining

Holiday cozy country cottage!

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Full Cottage at a Home from 1820, holiday rental in Ossining

Full Cottage at a Home from 1820

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful BRAND NEW 3 Bd Home Near West Point, holiday rental in Ossining

Beautiful BRAND NEW 3 Bd Home Near West Point

3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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The beautiful HillSide Cottage awaits you!  Great location and close to NY city!, holiday rental in Ossining

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Back Country Estate with Pool - Greenwich CT, holiday rental in Ossining

Back Country Estate with Pool - Greenwich CT

5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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5-Br 3-bath Skylit Home on 3 Forested Acres, holiday rental in Ossining

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

5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Serene Connecticut Retreat - Luxury 2 bedroom apt, holiday rental in Ossining

Serene Connecticut Retreat - Luxury 2 bedroom apt

2 bedrooms
2 bathrooms
Sleeps 4
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Quaint and immaculate 3 br duplex!, holiday rental in Ossining

Quaint and immaculate 3 br duplex!

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Croton Lodge: Luxury 2bd⭐Comfort+Style⭐45min to NYC., holiday rental in Ossining

Croton Lodge: Luxury 2bd⭐Comfort+Style⭐45min to NYC.

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Brand New! Walk to Train, Downtown Fully Loaded, holiday rental in Ossining

Brand New! Walk to Train, Downtown Fully Loaded

3 bedrooms
5 bathrooms
Sleeps 5
Match: Sleeps
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Greenwich Hotel Alternative / Boutique Living  - Fully Loaded- Turn Key 1B, holiday rental in Ossining

Greenwich Hotel Alternative / Boutique Living - Fully Loaded- Turn Key 1B

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Quaint Yonkers Condo - 1 Block to Hudson River!, holiday rental in Ossining

Quaint Yonkers Condo - 1 Block to Hudson River!

2 bedrooms
1 bathroom
Sleeps 6
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Modern,CloseToMetro/City,4BR/2BA, Free Parking- 35 minutes to NYC, holiday rental in Ossining

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

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Secluded Lakefront Cottage near Hudson Valley, holiday rental in Ossining

Secluded Lakefront Cottage near Hudson Valley

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Dominique's NYC Unique  2 Bedroom Pad-metro*wifi*safe neighborhood*quiet apt*, holiday rental in Ossining

Dominique's NYC Unique 2 Bedroom Pad-metro*wifi*safe neighborhood*quiet apt*

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Faces The Hudson + Only An Hour Outside NYC, holiday rental in Ossining

Faces The Hudson + Only An Hour Outside NYC

3 bedrooms
4 bathrooms
Sleeps 8
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'THE HILLTOP'-40Mins From NYC- Private Estate, holiday rental in Ossining

'THE HILLTOP'-40Mins From NYC- Private Estate

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Charming Rye Colonial Walk to Town & Train, holiday rental in Ossining

Charming Rye Colonial Walk to Town & Train

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Valhalla Sky 1 Queenn Rm, holiday rental in Ossining

Valhalla Sky 1 Queenn Rm

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Modern Comfy Studio 30 min from Manhattan - Yonkers NY, holiday rental in Ossining

Modern Comfy Studio 30 min from Manhattan - Yonkers NY

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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COZY RETREAT: HOT TUB, POOL, SAUNA, AND MORE..., holiday rental in Ossining

COZY RETREAT: HOT TUB, POOL, SAUNA, AND MORE...

5 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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Enchanting Hudson Valley Cottage Near Hiking!, holiday rental in Ossining

Enchanting Hudson Valley Cottage Near Hiking!

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Tentrr Signature Site - Downing Wood, holiday rental in Ossining

Tentrr Signature Site - Downing Wood

1 bedroom
1 bathroom
Sleeps 4
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Beautiful Private House; Golf, Hike, Fish, Swim, Relax, holiday rental in Ossining

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

2 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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DOMIR Garrison log cabin +hot tub+barrel sauna, holiday rental in Ossining

DOMIR Garrison log cabin +hot tub+barrel sauna

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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La Casita Bonita Near NYC, holiday rental in Ossining

La Casita Bonita Near NYC

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Sophisticated Country Living, holiday rental in Ossining

Sophisticated Country Living

4 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
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Walker's Paradise Steps from Greenwich Ave, holiday rental in Ossining

Walker's Paradise Steps from Greenwich Ave

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Emerald's Farm, holiday rental in Ossining

Emerald's Farm

5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Heart of Greenwich - Sun Drenched and Relaxing, holiday rental in Ossining

Heart of Greenwich - Sun Drenched and Relaxing

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bright & Airy Apartment w/ Balcony ~20 Mi to NYC!, holiday rental in Ossining

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Perfect Studio Getaway

0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
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Tentrr State Park Site - NY Harriman State Park - Midway at Silver Mine Lake, holiday rental in Ossining

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 Ossining

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 Ossining

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 Ossining

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 Ossining

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 Ossining

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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NEW! Updated Home w/ Patio Half Mile to West Point, holiday rental in Ossining

NEW! Updated Home w/ Patio Half Mile to West Point

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr State Park Site - NY Harriman State Park - Beaver Dam Silver Mine Lake, holiday rental in Ossining

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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Memory Lane Farm, holiday rental in Ossining

Memory Lane Farm

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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