Photo by Linda Zanetti

Search Villas 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
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 10 Villas in Ossining with updated reviews, rates, and availability.

Spacious Retreat w/ Pool, Hot Tub & Game Room
Interior

Spacious Retreat w/ Pool, Hot Tub & Game Room

Spacious Retreat w/ Pool, Hot Tub & Game Room
Lux Farmhouse Mansion, Pool, Pets, Hot Tub, Fire Pit, Hike, Private, 1 hr NYC
Exterior

Lux Farmhouse Mansion, Pool, Pets, Hot Tub, Fire Pit, Hike, Private, 1 hr NYC

10.0 out of 10, Exceptional, (77)
"Beautiful "
Lux Farmhouse Mansion, Pool, Pets, Hot Tub, Fire Pit, Hike, Private, 1 hr NYC
Luxury 5-Bdrm Getaway Near West Point
Property grounds

Luxury 5-Bdrm Getaway Near West Point

3.0 star property
10.0 out of 10, Exceptional, (2)
"seamless. Thank you. "
Luxury 5-Bdrm Getaway Near West Point
Kick back & relax in this peaceful, stylish place to stay with the whole family.
Fridge, microwave, oven, stovetop

Kick back & relax in this peaceful, stylish place to stay with the whole family.

10.0 out of 10, Exceptional, (24)
"Spacious and clean with a beautiful view of the mountains. We would stay there again."
Kick back & relax in this peaceful, stylish place to stay with the whole family.
Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT
Property grounds

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

9.0 out of 10, Wonderful, (6)
"Property was exactly what we were looking for with a group as large as ours (14 people). Plenty of indoor and outdoor space. Great kitchen as well (cooked all of our meals in the house for the whole group)."
Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT
Scenic Spring Home With Outdoor Dining Charm
Villa | 5 bedrooms

Scenic Spring Home With Outdoor Dining Charm

2.0 star property
Scenic Spring Home With Outdoor Dining Charm
Hudson Valley Estate on 4 Acres w/ Private Pool!
Dining

Hudson Valley Estate on 4 Acres w/ Private Pool!

Hudson Valley Estate on 4 Acres w/ Private Pool!
Historic Castle 1876 13 Mins to Wing Foot cc border of GREENWICH and New York
Exterior

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
Hudson Valley Estate on 4 Acres w/ Private Pool!
Interior

Hudson Valley Estate on 4 Acres w/ Private Pool!

3.0 star property
Hudson Valley Estate on 4 Acres w/ Private Pool!
NYC Hidden Chatteau
Interior

NYC Hidden Chatteau

NYC Hidden Chatteau
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
Sign in
Sign up, it's free

Frequently asked questions

Why book your villa in Ossining with Expedia?
We think vacation time shouldn’t be difficult, so if you’re looking for villas at an affordable price, Expedia can help. Stick to the budget and opt for an all-inclusive stay, or splurge on a high-end villa to spoil your nearest and dearest. Our search filters make it simple to find a retreat in Ossining that suits you best.
How can I find cheap villas in Ossining?
With Expedia’s helpful filter tool, reserving cheap villas in Ossining couldn’t be easier. To find accommodations that’ll make your wallet happy, narrow your search by amenities, star rating and budget.