Compare Ossining Villas

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Featured Villas in Ossining

Malkita Aria: Mountainview Escape with Postcard-Perfect Scenery

Malkita Aria: Mountainview Escape with Postcard-Perfect Scenery

Woodbury NY
This villa offers a gym, a sauna, and a hot tub. Other amenities at this family-friendly villa include an arcade/game room, laundry facilities, and barbecue grills.
Hot Tub
Kitchen
Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge

Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge

Stony Point NY
Guests of this villa enjoy features like an outdoor pool, a hot tub, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities, barbecue grills, and a garden.
Pool
Hot Tub
Warm Escape, Wood Stove, HotTub, Pets, <1 Hr NYC

Warm Escape, Wood Stove, HotTub, Pets, <1 Hr NYC

Harriman NY
At this villa, guests have access to an arcade/game room, laundry facilities, and a garden. This family-friendly villa also has barbecue grills.
Pool
Kitchen
Spacious Retreat w/ Pool, Hot Tub & Game Room

Spacious Retreat w/ Pool, Hot Tub & Game Room

Stony Point NY
At this villa, guests have access to features like laundry facilities.
Washer
Dryer
Family Retreat with Autumn Views and Game Room

Family Retreat with Autumn Views and Game Room

3 out of 5
Stony Point NY
Guests of this villa enjoy features like a gym, a hot tub, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities, a garden, and barbecue grills.
Pool
Hot Tub
Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT

Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT

Brewster NY
Guests staying at this villa enjoy a gym, an arcade/game room, and laundry facilities. This smoke-free villa also has barbecue grills.
Pool
Kitchen
Family Retreat With Autumn Views and Fireplace

Family Retreat With Autumn Views and Fireplace

2 out of 5
Stony Point NY
Guests staying at this villa enjoy a gym, free WiFi in public areas, and a garden. Free parking is included with your stay.
Parking included
Free WiFi
Hudson Valley Estate on 4 Acres w/ Private Pool!

Hudson Valley Estate on 4 Acres w/ Private Pool!

3 out of 5
Nyack NY
Guests staying at this villa enjoy access to a marina, an outdoor pool, and free WiFi in public areas. You can take advantage of free parking if you drive. This smoke-free villa also has a garden.
Pool
Kitchen
Historic Castle 1876 13 Mins to Wing Foot cc border of GREENWICH and New York

Historic Castle 1876 13 Mins to Wing Foot cc border of GREENWICH and New York

Rye Brook NY
At this villa, guests have access to features like laundry facilities. This smoke-free villa also has barbecue grills.
Kitchen
Washer
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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.

Hotel Options in Ossining

    Windrose On Hudson

    Windrose On Hudson

    1 Shady Lane Farm Road Ossining NY
    $197 nightly
    The price is $220 total per night from Jan 4 to Jan 5
    $220 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    8/10 Very Good! (101 reviews)
    Baymont by Wyndham White Plains - Elmsford

    Baymont by Wyndham White Plains - Elmsford

    540 Saw Mill River Rd Elmsford NY
    $126 nightly
    The price is $144 total per night from Jan 4 to Jan 5
    $144 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    8.2/10 Very Good! (1,460 reviews)
    Ramada by Wyndham Bronx

    Ramada by Wyndham Bronx

    1000 Baychester Ave Bronx NY
    $128 nightly
    The price is $151 total per night from Jan 11 to Jan 12
    $151 total
    Jan 11 - Jan 12, 2026
    Total with taxes and fees
    8.2/10 Very Good! (1,006 reviews)

Luxury Villas

Book luxury villas in Ossining
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Ossining. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Ossining, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Ossining
You won’t have a problem finding your own space in Ossining. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Ossining on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Ossining rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Ossining Villas essential information

Accommodation
10 Villas
Lowest Price
$144
Highest Price
$220
Popular accommodation
Malkita Aria: Mountainview Escape with Postcard-Perfect Scenery, Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge, Warm Escape, Wood Stove, HotTub, Pets, <1 Hr NYC, Spacious Retreat w/ Pool, Hot Tub & Game Room, Family Retreat with Autumn Views and Game Room, Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT, Family Retreat With Autumn Views and Fireplace, Hudson Valley Estate on 4 Acres w/ Private Pool!, Historic Castle 1876 13 Mins to Wing Foot cc border of GREENWICH and New York