Photo by Linda Zanetti

Search Vacation Homes in Ossining

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

Compare 347 Vacation Homes in Ossining with updated reviews, rates, and availability.

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Fridge, microwave, stovetop, dishwasher

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

10.0 out of 10, Exceptional, (34)
"Perfect for our family’s visit to West Point. Great location "
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Fridge, microwave, oven, stovetop

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

9.0 out of 10, Wonderful, (27)
"Perfect place and plenty of parking. "
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Modern 4BD/3BA w/Parking & deck & 29 min>NYC
Point of interest

Modern 4BD/3BA w/Parking & deck & 29 min>NYC

9.6 out of 10, Exceptional, (10)
"House was very nice and roomy. Area was nice also. Had an issue upstairs with refrigerator but used downstairs one as a backup."
Modern 4BD/3BA w/Parking & deck & 29 min>NYC
Bright Cornwall-On-Hudson Vacation Rental!
Fridge, microwave, stovetop, dishwasher

Bright Cornwall-On-Hudson Vacation Rental!

9.8 out of 10, Exceptional, (14)
"Nice location. Clean and comfortable. Was very cold inside when we entered (52 degrees) and I could not find an extra blanket anywhere. Everything else was great. "
Bright Cornwall-On-Hudson Vacation Rental!
Luxury 3Bed Private Apartment Near Manhattan
Smart TV, computer monitors, printers

Luxury 3Bed Private Apartment Near Manhattan

9.2 out of 10, Wonderful, (11)
"Host was very accommodating and easy to communicate with!"
The price is SAR 1,219
SAR 1,984 total
includes taxes & fees
5 Apr - 6 Apr
Luxury 3Bed Private Apartment Near Manhattan
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
Fridge, microwave, oven, stovetop

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (96)
"House is absolutely perfect! This is our second time staying and we will definitely return. So much charm and warmth. I had the best sleep that I have had in months. All the amenities you could ask for, and more. Terrific convenient location. Host goes above and beyond to make sure we are comfortable. "
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
Contemporary Cozy Cottage
Interior

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (16)
"This is a fully decked out house with cozy beds, full kitchen, completely up to date amenities. The host is very accessible, polite, and helpful."
The price is SAR 938
SAR 1,399 total
includes taxes & fees
9 Apr - 10 Apr
Contemporary Cozy Cottage
Modern, Magical Woodsy Escape 1 Hour From NYC
Fridge, microwave, oven, stovetop

Modern, Magical Woodsy Escape 1 Hour From NYC

10.0 out of 10, Exceptional, (22)
"The home was beautiful, comfortable and so spacious. Great time with friends made even better by the location. The amenities were great, beds were so comfortable and quality toiletries provided. Would definitely considering coming back. Not one complaint. Host set us up to have a winderful weekend. "
Modern, Magical Woodsy Escape 1 Hour From NYC
Over Sized Colonial on Private Road.
Exterior

Over Sized Colonial on Private Road.

9.6 out of 10, Exceptional, (39)
"The home was spacious and provided recreation for kids with hot tub, gym, ping pong, foosball, and game. However, property was advertised as 9 bedrooms and 7 baths. My family looked forward to spreading out but 4 bedrooms with adjoining bathrooms were locked. Text host to see if he would open them but he declined. That was disappointing."
Over Sized Colonial on Private Road.
New Beach Home near Stamford Downtown/Shippan
Terrace/patio

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (20)
"Great home with fun ping pong table!"
The price is SAR 2,434
SAR 4,255 total
includes taxes & fees
13 Apr - 14 Apr
New Beach Home near Stamford Downtown/Shippan
Charming 2-bedroom house with AC, WiFi in marvelous Nyack
Private kitchen

Charming 2-bedroom house with AC, WiFi in marvelous Nyack

2.0 star property
Charming 2-bedroom house with AC, WiFi in marvelous Nyack
Lovely 3BR Home with parking-Walk to WP Gate!
TV

Lovely 3BR Home with parking-Walk to WP Gate!

10.0 out of 10, Exceptional, (2)
"Close to west point where we were able to attend the sporting event. It is walking distance to the small town outside campus where you can find local shops for eating or shopping. ."
The price is SAR 654
SAR 1,062 total
includes taxes & fees
31 Mar - 1 Apr
Lovely 3BR Home with parking-Walk to WP Gate!
The Woodbury Cottage
Terrace/patio

The Woodbury Cottage

8.6 out of 10, Excellent, (18)
"Great little cottage, nice neighborhood and close to everything "
The Woodbury Cottage
Perfect for families and large groups
A heated pool

Perfect for families and large groups

9.6 out of 10, Exceptional, (12)
"The property is beautiful and was perfect for our stay. We were in town to see a family members art exhibit. It was my father first stay at a rental property like this and was a good experience for him. We really enjoyed the game room and projecter tv to watch the Superbowl! It was a great place for our family to come together. Thank you!"
Perfect for families and large groups
Charming Hudson Valley 3-Bedroom Family Getaway
Fridge, microwave, oven, stovetop

Charming Hudson Valley 3-Bedroom Family Getaway

8.0 out of 10, Very Good, (2)
"Nice entryway, lots of room for shoes. 1st and 3rd floor bedrooms were spacious. Nice size livingroom. Need more cookware for kitchen, and would recommend fixing the exhaust fan in the bathroom, and a better foundation for the attic bed. Moving slats caused the mattress to sag, especially at the foot of the bed. We would stay again. "
The price is SAR 658
SAR 1,103 total
includes taxes & fees
8 Apr - 9 Apr
Charming Hudson Valley 3-Bedroom Family Getaway
Cozy and beautiful house
Interior

Cozy and beautiful house

10.0 out of 10, Exceptional, (21)
"A movie was being produced at our home.We needed to relocate for the week.We loved the house. All the rooms were clean & organized . Kitchen was well equipped .We met the neighbors! Lovely people !The only draw back is the stairs. Bathrooms are upstairs & in finished basement , but otherwise lovely"
Cozy and beautiful house
Charming Mamaroneck Home ~ 22 Mi to Manhattan
TV

Charming Mamaroneck Home ~ 22 Mi to Manhattan

7.8 out of 10, Good, (11)
"Clean and easy check in--Great Location!"
Charming Mamaroneck Home ~ 22 Mi to Manhattan
Ossining Vacation Rental Near River, Trails & MTA!
Fridge, microwave, stovetop, dishwasher

Ossining Vacation Rental Near River, Trails & MTA!

8.4 out of 10, Very Good, (7)
"This was our Christmas gathering place for family from 4 states. Beautiful home and location. "
Ossining Vacation Rental Near River, Trails & MTA!
Luxe Living: Pool, Playground & Fireplace
Interior

Luxe Living: Pool, Playground & Fireplace

10.0 out of 10, Exceptional, (1)
Luxe Living: Pool, Playground & Fireplace
West Point Family Retreat, 5 min walk to Thayer!
Exterior

West Point Family Retreat, 5 min walk to Thayer!

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great house and right outside West Point"
The price is SAR 1,688
SAR 2,826 total
includes taxes & fees
7 Apr - 8 Apr
West Point Family Retreat, 5 min walk to Thayer!
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.
Don't see what you're looking for?
See all available properties in Ossining
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Ossining

Global Luxury Suites White Plains
Reception

Global Luxury Suites White Plains

3.5 star property
6.6 out of 10, (30)
"I was very impressed with this "hotel". It is more of an AirBB as your unit is an apartment in an apartment building with permant residents. It comes nicely furnished, including basic kitchen essentials (like service for four, pots and pans, coffee maker, etc). All of the amenities are modern, and the in-unit washer dryer is a huge plus. I also really appreciated some of the welcome gifts, including some coffee/tea, laundry detergent, and your basic hygiene essentials. Property communicates...
Global Luxury Suites White Plains
Stamford Suites
Exterior

Stamford Suites

3.0 star property
7.0 out of 10, Good, (575)
"Room was very spacious "
The price is SAR 623
SAR 716 total
includes taxes & fees
24 Apr - 25 Apr
Stamford Suites
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (108)
"Awesome "
The price is SAR 671
SAR 979 total
includes taxes & fees
2 Apr - 3 Apr
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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.