Ossining Station holiday lettings
We found 755 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:7 Nov - 14 Nov
Image gallery for Hudson River Valley Estate - New Listing!
1010 out of 10 rating
Exceptional
(7 reviews)
Hudson River Valley Estate - New Listing!
Verplanck, NY
11% off
Price is £8,797
£8,797
£1,257 per night
includes taxes & fees
Image gallery for Faces The Hudson + Only An Hour Outside NYC
1010 out of 10 rating
Exceptional
(17 reviews)
Faces The Hudson + Only An Hour Outside NYC
Haverstraw, NY
16% off
Price is £3,013
£3,013
£430 per night
includes taxes & fees
Image gallery for RAIN, SNOW OR SHINE! THIS HOUSE HAS ALL YOU NEED AND MORE TO HAVE A GOOD TIME !
1010 out of 10 rating
Exceptional
(5 reviews)
RAIN, SNOW OR SHINE! THIS HOUSE HAS ALL YOU NEED AND MORE TO HAVE A GOOD TIME !
Pound Ridge, NY
5% off
Price is £8,133
£8,133
£1,162 per night
includes taxes & fees
Image gallery for Fun, Friends, and Family Lakefront Home w/Dock and Beach
1010 out of 10 rating
Exceptional
(12 reviews)
Fun, Friends, and Family Lakefront Home w/Dock and Beach
Mahopac, NY
12% off
Price is £3,641
£3,641
£520 per night
includes taxes & fees
Image gallery for Charming 3-bedroom house.
1010 out of 10 rating
Exceptional
(9 reviews)
Charming 3-bedroom house.
Cortlandt, NY
7% off
Price is £1,840
£1,840
£263 per night
includes taxes & fees
Image gallery for 3 Mi to Downtown: Spacious White Plains Home
9.69.6 out of 10 rating
Exceptional
(5 reviews)
3 Mi to Downtown: Spacious White Plains Home
White Plains, NY
18% off
Price is £3,422
£3,422
£489 per night
includes taxes & fees
Image gallery for Contemporary Cozy Cottage
1010 out of 10 rating
Exceptional
(26 reviews)
Contemporary Cozy Cottage
Lake Peekskill, NY
8% off
Price is £1,597
£1,597
£228 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 £10,882
£10,882
£1,555 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, NY
6% off
Price is £6,377
£6,377
£911 per night
includes taxes & fees
Image gallery for Aspen In Airmont NY
1010 out of 10 rating
Exceptional
(6 reviews)
Aspen In Airmont NY
Monsey, NY
7% off
Price is £5,428
£5,428
£775 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
15% off
Price is £4,807
£4,807
£687 per night
includes taxes & fees
Image gallery for Peaceful Cottage with Grill | Walk to Lake
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Peaceful Cottage with Grill | Walk to Lake
Putnam Valley, NY
7% off
Price is £2,627
£2,627
£375 per night
includes taxes & fees
Image gallery for Relaxing & Great Location & Minutes from New York
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Relaxing & Great Location & Minutes from New York
Tarrytown, NY
14% off
Price is £2,163
£2,163
£309 per night
includes taxes & fees
Image gallery for Stunning views, 3-bedroom house in delightful Croton-on-Hudson with WiFi, AC
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Stunning views, 3-bedroom house in delightful Croton-on-Hudson with WiFi, AC
Croton-on-Hudson, NY
7% off
Price is £2,836
£2,836
£405 per night
includes taxes & fees
Image gallery for Stylish downstairs apartment. Walk to town, train, & beach ferry!
1010 out of 10 rating
Exceptional
(20 reviews)
Stylish downstairs apartment. Walk to town, train, & beach ferry!
Greenwich, CT
7% off
Price is £2,184
£2,184
£312 per night
includes taxes & fees
Image gallery for Chic, Modern & Cozy~Walk to Train~Free Parking NYC
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Chic, Modern & Cozy~Walk to Train~Free Parking NYC
New Rochelle, NY
8% off
Price is £2,164
£2,164
£309 per night
includes taxes & fees
Image gallery for PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
9.09.0 out of 10 rating
Wonderful
(36 reviews)
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Yonkers, NY
7% off
Price is £1,518
£1,518
£217 per night
includes taxes & fees
Image gallery for Charming duplex with private yard. Close to the beach, dining & shopping!
9.89.8 out of 10 rating
Exceptional
(40 reviews)
Charming duplex with private yard. Close to the beach, dining & shopping!
Greenwich, CT
7% off
Price is £1,632
£1,632
£233 per night
includes taxes & fees
Image gallery for ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home
1010 out of 10 rating
Exceptional
(25 reviews)
ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home
Stamford, CT
9% off
Price is £2,884
£2,884
£412 per night
includes taxes & fees
Image gallery for 6 Bedroom Elegant and Comfy Upstate Oasis SANITIZED
1010 out of 10 rating
Exceptional
(22 reviews)
6 Bedroom Elegant and Comfy Upstate Oasis SANITIZED
Carmel, NY
8% off
Price is £7,279
£7,279
£1,040 per night
includes taxes & fees
Image gallery for Quaint duplex with private yard. Walk to beach, dining, & shopping!
1010 out of 10 rating
Exceptional
(44 reviews)
Quaint duplex with private yard. Walk to beach, dining, & shopping!
Greenwich, CT
7% off
Price is £1,769
£1,769
£253 per night
includes taxes & fees
Image gallery for Mid Century Modern ZEN House with Pool. 50 min from New York City
1010 out of 10 rating
Exceptional
(19 reviews)
Mid Century Modern ZEN House with Pool. 50 min from New York City
Stamford, CT
20% off
Price is £2,247
£2,247
£321 per night
includes taxes & fees
Image gallery for Luxury 3Bed Private Apartment Near Manhattan
9.29.2 out of 10 rating
Wonderful
(19 reviews)
Luxury 3Bed Private Apartment Near Manhattan
New Rochelle, NY
15% off
Price is £2,797
£2,797
£400 per night
includes taxes & fees
Image gallery for The Subterranean Haven
9.09.0 out of 10 rating
Wonderful
(8 reviews)
The Subterranean Haven
Mount Vernon, NY
8% off
Price is £1,149
£1,149
£164 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Ossining Station
Garrison Woods Getaway: Guest House w/ Screened Porch and Mountain Views
Sleeps 2 · 1 bedroom · 1 bathroom
Walk to WP Gate + Free Parking!
Sleeps 6 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
Global Luxury Suites White Plains
Sleeps 5 · 2 bedrooms
6.86.8 out of 10
31 reviews(31 reviews)
Modern Luxury Loft with Artful Vibes
Sleeps 4 · 2 bedrooms · 1 bathroom
Stamford Grand Apartment + Cozy Den
Sleeps 5 · 1 bedroom · 1 bathroom
8.48.4 out of 10
Very goodvery good
5 reviews(5 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, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value