Ossining Station holiday homes
We found 723 holiday rentals — enter your dates for availability
Take a look at holiday rentals within easy reach of Ossining Station that provide the perfect home base for your trip. Whether you're going on holiday with family or friends, holiday homes have the best amenities for spending time at your holiday home, which might include Wi-Fi and a hot tub. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Ossining Station
Showing deals for:1 Aug - 8 Aug
Image gallery for GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS
1010 out of 10 rating
Exceptional
(19 reviews)
GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS
Mamaroneck, NY
8% off
Price is NZ$33,445
NZ$33,445
NZ$4,778 per night
includes taxes & fees
Image gallery for Waterfront Retreat Center for Health & Wellness
9.69.6 out of 10 rating
Exceptional
(56 reviews)
Waterfront Retreat Center for Health & Wellness
New Rochelle, NY
11% off
Price is NZ$17,880
NZ$17,880
NZ$2,554 per night
includes taxes & fees
Image gallery for Hudson River Views + Firepit, Patio, Dog Run, Game Room | Stone Manor
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Hudson River Views + Firepit, Patio, Dog Run, Game Room | Stone Manor
Briarcliff Manor, New York
18% off
Price is NZ$11,201
NZ$11,201
NZ$1,600 per night
includes taxes & fees
Image gallery for Stunning Mansion, Pool, Pets, Hot Tub, Fire Pit, Hike, Secluded luxury, 1 hr NYC
1010 out of 10 rating
Exceptional
(77 reviews)
Stunning Mansion, Pool, Pets, Hot Tub, Fire Pit, Hike, Secluded luxury, 1 hr NYC
Harriman, NY
8% off
Price is NZ$33,878
NZ$33,878
NZ$4,840 per night
includes taxes & fees
Image gallery for Bear Mountain House.
1010 out of 10 rating
Exceptional
(14 reviews)
Bear Mountain House.
Garrison, NY
8% off
Price is NZ$8,487
NZ$8,487
NZ$1,212 per night
includes taxes & fees
Image gallery for Minutes to NYC Private house in quite Neiborhood, walking distance to Starbucks
8.08.0 out of 10 rating
Very good
(5 reviews)
Minutes to NYC Private house in quite Neiborhood, walking distance to Starbucks
Mount Vernon, NY
8% off
Price is NZ$8,060
NZ$8,060
NZ$1,151 per night
includes taxes & fees
Image gallery for Beautiful private guesthouse in Larchmont
1010 out of 10 rating
Exceptional
(7 reviews)
Beautiful private guesthouse in Larchmont
Larchmont, NY
8% off
Price is NZ$4,777
NZ$4,777
NZ$682 per night
includes taxes & fees
Image gallery for Newly Renovated Cozy 2 Bedroom Apartment with 3 min walk to Main Street
1010 out of 10 rating
Exceptional
(7 reviews)
Newly Renovated Cozy 2 Bedroom Apartment with 3 min walk to Main Street
Tarrytown, NY
8% off
Price is NZ$5,218
NZ$5,218
NZ$745 per night
includes taxes & fees
Image gallery for Luxury 3Bed Private Apartment Near Manhattan
9.29.2 out of 10 rating
Wonderful
(12 reviews)
Luxury 3Bed Private Apartment Near Manhattan
New Rochelle, NY
12% off
Price is NZ$5,457
NZ$5,457
NZ$780 per night
includes taxes & fees
Image gallery for 2nd Floor, 1 Br / 1 Ba With Sofa Bed In The Living Room
9.89.8 out of 10 rating
Exceptional
(10 reviews)
2nd Floor, 1 Br / 1 Ba With Sofa Bed In The Living Room
Greenwich, CT
7% off
Price is NZ$1,919
NZ$1,919
NZ$274 per night
includes taxes & fees
Image gallery for Home To Rent For West Point Activities, PCS Moves, and TDY
9.49.4 out of 10 rating
Exceptional
(21 reviews)
Home To Rent For West Point Activities, PCS Moves, and TDY
Fort Montgomery, NY
10% off
Price is NZ$6,255
NZ$6,255
NZ$894 per night
includes taxes & fees
Image gallery for Charming 3-bedroom house.
1010 out of 10 rating
Exceptional
(6 reviews)
Charming 3-bedroom house.
Cortlandt, NY
8% off
Price is NZ$3,961
NZ$3,961
NZ$566 per night
includes taxes & fees
Image gallery for Historic 6-Bdrm Tudor Estate w pool/tennis access
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Historic 6-Bdrm Tudor Estate w pool/tennis access
Stamford, CT
8% off
Price is NZ$20,478
NZ$20,478
NZ$2,925 per night
includes taxes & fees
Image gallery for Modern Highland Falls House near USMA - 3 bed, 2 bath w/ Hot tub & Fire pit!
1010 out of 10 rating
Exceptional
(10 reviews)
Modern Highland Falls House near USMA - 3 bed, 2 bath w/ Hot tub & Fire pit!
Highland Falls, NY
11% off
Price is NZ$5,516
NZ$5,516
NZ$788 per night
includes taxes & fees
Image gallery for Contemporary Cozy Cottage
1010 out of 10 rating
Exceptional
(17 reviews)
Contemporary Cozy Cottage
Lake Peekskill, NY
8% off
Price is NZ$3,388
NZ$3,388
NZ$484 per night
includes taxes & fees
Image gallery for Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
1010 out of 10 rating
Exceptional
(21 reviews)
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Rye Brook, NY
8% off
Price is NZ$3,079
NZ$3,079
NZ$440 per night
includes taxes & fees
Image gallery for Cozy House 3 Blocks From West Pt
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Cozy House 3 Blocks From West Pt
Highland Falls, NY
8% off
Price is NZ$6,040
NZ$6,040
NZ$863 per night
includes taxes & fees
Image gallery for 6 Bedroom Elegant and Comfy Upstate Oasis SANITIZED
1010 out of 10 rating
Exceptional
(18 reviews)
6 Bedroom Elegant and Comfy Upstate Oasis SANITIZED
Carmel, NY
8% off
Price is NZ$25,278
NZ$25,278
NZ$3,611 per night
includes taxes & fees
Image gallery for Discover fun at NYC 30min drive stay at our cozy 2bed apartment in New Rochelle
9.09.0 out of 10 rating
Wonderful
(16 reviews)
Discover fun at NYC 30min drive stay at our cozy 2bed apartment in New Rochelle
New Rochelle, NY
11% off
Price is NZ$2,228
NZ$2,228
NZ$318 per night
includes taxes & fees
Image gallery for New Jersey home, close to NY City Fun!
8.88.8 out of 10 rating
Excellent
(6 reviews)
New Jersey home, close to NY City Fun!
Englewood, NJ
8% off
Price is NZ$5,269
NZ$5,269
NZ$753 per night
includes taxes & fees
Image gallery for Ultra Secluded mountaintop mansion amazing views-hot tub-arcade
8.48.4 out of 10 rating
Very good
(18 reviews)
Ultra Secluded mountaintop mansion amazing views-hot tub-arcade
Mahopac, NY
8% off
Price is NZ$11,851
NZ$11,851
NZ$1,693 per night
includes taxes & fees
Image gallery for Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.89.8 out of 10 rating
Exceptional
(109 reviews)
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery, NY
10% off
Price is NZ$2,614
NZ$2,614
NZ$373 per night
includes taxes & fees
Image gallery for Colorful, Comfy & Modern - Close to NYC - Parking!
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Colorful, Comfy & Modern - Close to NYC - Parking!
Mount Vernon, NY
8% off
Price is NZ$3,034
NZ$3,034
NZ$433 per night
includes taxes & fees
Image gallery for NewRo Chic Retreat- 3 Bdrms 30 min to NYC
1010 out of 10 rating
Exceptional
(5 reviews)
NewRo Chic Retreat- 3 Bdrms 30 min to NYC
New Rochelle, NY
24% off
Price is NZ$4,237
NZ$4,237
NZ$605 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Ossining Station
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Sleeps 4 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
109 reviews(109 reviews)
Cozy house on the Hudson
Sleeps 2 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
48 reviews(48 reviews)
Relaxing & Great Location & Minutes from New York
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
Hudson River Views + Firepit, Patio, Dog Run, Game Room | Stone Manor
Sleeps 12 · 4 bedrooms · 3+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Stunning views, 3-bedroom house in delightful Croton-on-Hudson with WiFi, AC
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
Hudson Valley Getaway for Families
Sleeps 12 · 6 bedrooms · 2+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
90 reviews(90 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value