Holiday rentals near Ossining Historical Society
We found 772 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:14 Nov - 21 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 S$15,469
S$15,469
S$2,210 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 S$3,103
S$3,103
S$443 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
17% off
Price is S$5,034
S$5,034
S$719 per night
includes taxes & fees
Image gallery for Spacious 3b/3b Mediterranean in White Plains
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Spacious 3b/3b Mediterranean in White Plains
White Plains, NY
8% off
Price is S$3,973
S$3,973
S$568 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 S$6,522
S$6,522
S$932 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 S$5,907
S$5,907
S$844 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 S$14,075
S$14,075
S$2,011 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 S$5,725
S$5,725
S$818 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
15% off
Price is S$2,437
S$2,437
S$348 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
19% off
Price is S$6,775
S$6,775
S$968 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 S$19,246
S$19,246
S$2,749 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 S$2,528
S$2,528
S$361 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 S$9,347
S$9,347
S$1,335 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 S$7,952
S$7,952
S$1,136 per night
includes taxes & fees
Image gallery for Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
1010 out of 10 rating
Exceptional
(24 reviews)
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Rye Brook, NY
8% off
Price is S$2,360
S$2,360
S$337 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 S$2,067
S$2,067
S$295 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 S$8,245
S$8,245
S$1,178 per night
includes taxes & fees
Image gallery for Bright Stylish Chic 4BR 4BA Home Pet Friendly!
1010 out of 10 rating
Exceptional
(102 reviews)
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
Stamford, CT
8% off
Price is S$5,562
S$5,562
S$795 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 S$4,672
S$4,672
S$667 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
15% off
Price is S$3,626
S$3,626
S$518 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 S$3,702
S$3,702
S$529 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 S$3,649
S$3,649
S$521 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 S$2,550
S$2,550
S$364 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
(8 reviews)
Newly Renovated Cozy 2 Bedroom Apartment with 3 min walk to Main Street
Tarrytown, NY
8% off
Price is S$4,799
S$4,799
S$686 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 Historical Society
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)
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)
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
9.09.0 out of 10
Wonderfulwonderful
7 reviews(7 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