Photo by Linda Zanetti

Search Vacation Homes in Ossining

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

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

8.8 out of 10, Excellent, (28)
"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, (11)
"Great location! Cozy property! Accommodated our group nicely! If you are visiting NY and don’t want to be in the city check this place out."
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, (13)
"Apartment was large spacious and clean. Check in a but stressful. Requested. 30 mintue early check in so my daughters and i could get ready for a wedding we were attending. Host could not give a definitive answer and check in instructions werent sent but 20 minutes before check in. NO PARKING. 30 mintues driving around at midnight to find a spot 6 blockes away. Thats a long walk in heels aftering dancing all night! LoL. I dont know the area so I assumed there would be parking. I will ask from...
The price is AED 1,194
AED 2,248 total
includes taxes & fees
30 Apr - 1 May
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, (18)
"Clean, beautiful and comfortable! A woodsy retreat close to Peekskill. We will book again for sure! "
The price is AED 918
AED 1,497 total
includes taxes & fees
4 May - 5 May
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, (24)
"Clean, large, well stocked kitchen. Everything you could want from a VRBO."
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!"
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!
Interior

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 AED 525
AED 993 total
includes taxes & fees
30 Apr - 1 May
Lovely 3BR Home with parking-Walk to WP Gate!
The Woodbury Cottage
Terrace/patio

The Woodbury Cottage

8.8 out of 10, Excellent, (19)
"Really enjoyed our stay at this comfy cottage. Easily slept a family of 3 with plenty of room to lounge around. It's an older cottage, but the owner has added a lot of neat touches that make this a nice place to stay in this area."
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 AED 775
AED 1,369 total
includes taxes & fees
12 May - 13 May
Charming Hudson Valley 3-Bedroom Family Getaway
Cozy and beautiful house
Interior

Cozy and beautiful house

9.8 out of 10, Exceptional, (24)
"Great stay and near Sarah Lawrence College"
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, (12)
"The property is as advertised. It's spacious and the beds are comfortable; it was clean when we arrived. The kitchen was well equipped - pretty much everything you could want (except, as one previous guest noted, bowls, and dish cloths). Rogerta responded promptly to emails with small questions and we didn't have any issues during our stay. As noted there is a second apartment in the building and you can occasionally hear talking or the TV, but it was not at volume or enough to disturb anyone...
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, (3)
"Nice houseAwesome kitchen Granddaughter loved the bunk bed and the many games"
The price is AED 1,653
AED 3,037 total
includes taxes & fees
30 Apr - 1 May
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

Stamford Suites
Exterior

Stamford Suites

3.0 star property
5.8 out of 10, (28)
"Convenience. Full kitchen and spacious rooms"
The price is AED 691
AED 794 total
includes taxes & fees
30 Apr - 1 May
Stamford Suites
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
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, (109)
"We enjoyed our stay. The views are great and the space comfortable. It worked well for our visit with family living nearby and visiting Bear Mountain."
The price is AED 617
AED 1,018 total
includes taxes & fees
30 Apr - 1 May
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.