
Holiday rentals near Ossining Historical Society
We found 760 holiday rentals — enter your dates for availability
Select the perfect holiday home within close proximity to Ossining Historical Society. Holiday rentals provide the amenities that you need and want for your family, friends or furry companion, such as Wi-Fi and a pool. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Ossining Historical Society
Showing deals for:7 Nov - 14 Nov
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 NZ$18,102
NZ$18,102
NZ$2,586 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 NZ$3,548
NZ$3,548
NZ$507 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$24,555
NZ$24,555
NZ$3,508 per night
includes taxes & fees
Image gallery for Mid-Century Modern Hilltop Retreat

9.09.0 out of 10 rating
Wonderful
(9 reviews)
Mid-Century Modern Hilltop Retreat
South Salem, NY
12% off
Price is NZ$9,889
NZ$9,889
NZ$1,413 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
8% off
Price is NZ$4,999
NZ$4,999
NZ$714 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 NZ$4,090
NZ$4,090
NZ$584 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 NZ$7,811
NZ$7,811
NZ$1,116 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
6% off
Price is NZ$14,398
NZ$14,398
NZ$2,057 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
8% off
Price is NZ$11,857
NZ$11,857
NZ$1,694 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, New York
18% off
Price is NZ$7,764
NZ$7,764
NZ$1,109 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 NZ$6,740
NZ$6,740
NZ$963 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
16% off
Price is NZ$10,477
NZ$10,477
NZ$1,497 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 NZ$16,241
NZ$16,241
NZ$2,320 per night
includes taxes & fees
Image gallery for The Fred Deluxe 7 BR by I95, Train, HarborVw, Stamford Beaches & Workspace

8.68.6 out of 10 rating
Excellent
(7 reviews)
The Fred Deluxe 7 BR by I95, Train, HarborVw, Stamford Beaches & Workspace
Stamford, CT
8% off
Price is NZ$10,033
NZ$10,033
NZ$1,433 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 NZ$5,080
NZ$5,080
NZ$726 per night
includes taxes & fees
Image gallery for Relaxing & Great Location & Minutes from New York

8.88.8 out of 10 rating
Excellent
(6 reviews)
Relaxing & Great Location & Minutes from New York
Tarrytown, NY
14% off
Price is NZ$4,853
NZ$4,853
NZ$693 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
8% off
Price is NZ$4,866
NZ$4,866
NZ$695 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 NZ$4,987
NZ$4,987
NZ$712 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 NZ$3,636
NZ$3,636
NZ$519 per night
includes taxes & fees
Image gallery for The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!.

1010 out of 10 rating
Exceptional
(11 reviews)
The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!.
Brewster, NY
13% off
Price is NZ$3,857
NZ$3,857
NZ$551 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 NZ$3,939
NZ$3,939
NZ$563 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
8% off
Price is NZ$6,256
NZ$6,256
NZ$894 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
(118 reviews)
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery, NY
10% off
Price is NZ$2,634
NZ$2,634
NZ$376 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 NZ$3,362
NZ$3,362
NZ$480 per night
includes taxes & fees
Find spaces that suit your style
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Villa
Chalet
Find the best place to stay - Ossining Historical Society
Stunning views, 3-bedroom house in delightful Croton-on-Hudson with WiFi, AC
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Sleeps 4 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
118 reviews(118 reviews)
Cozy house on the Hudson
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
56 reviews(56 reviews)
Ideal Location 1block to Main St. Restaurants , Bars,Hudson River, Bus/ Train
Sleeps 4 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Relaxing & Great Location & Minutes from New York
Sleeps 8 · 4 bedrooms · 2 bathrooms
8.88.8 out of 10
Excellentexcellent
6 reviews(6 reviews)
Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.
Sleeps 8 · 4 bedrooms · 4 bathrooms
9.09.0 out of 10
Wonderfulwonderful
6 reviews(6 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