Photo by Linda Zanetti
Search Vacation Homes in Ossining
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 347 Vacation Homes in Ossining with updated reviews, rates, and availability.

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
10.0 out of 10, Exceptional, (34)

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
8.8 out of 10, Excellent, (28)

Modern 4BD/3BA w/Parking & deck & 29 min>NYC
Modern 4BD/3BA w/Parking & deck & 29 min>NYC
9.6 out of 10, Exceptional, (11)

Bright Cornwall-On-Hudson Vacation Rental!
Bright Cornwall-On-Hudson Vacation Rental!
9.8 out of 10, Exceptional, (14)

Luxury 3Bed Private Apartment Near Manhattan
Luxury 3Bed Private Apartment Near Manhattan
9.2 out of 10, Wonderful, (12)
The price is AED 1,194
AED 2,243 total
includes taxes & fees
1 May - 2 May

Bright Stylish Chic 4BR 4BA Home Pet Friendly!
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
10.0 out of 10, Exceptional, (96)

Contemporary Cozy Cottage
Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (17)
The price is AED 918
AED 1,497 total
includes taxes & fees
20 May - 21 May

Modern, Magical Woodsy Escape 1 Hour From NYC
Modern, Magical Woodsy Escape 1 Hour From NYC
10.0 out of 10, Exceptional, (23)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Ossining

Stamford Suites
Stamford Suites
5.8 out of 10, (28)
The price is AED 691
AED 794 total
includes taxes & fees
30 Apr - 1 May

Global Luxury Suites White Plains
Global Luxury Suites White Plains
6.6 out of 10, (30)

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (109)
The price is AED 617
AED 1,018 total
includes taxes & fees
30 Apr - 1 May
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Recent reviews of Ossining hotels
Recent reviews of Ossining hotels

Ardsley Acres Hotel Westchester
5/5 Excellent
"Very clean! "
A verified traveler stayed at Ardsley Acres Hotel Westchester
Posted 17 hours ago