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Check prices for these dates

Next weekend
20 Jun - 22 Jun
In two weeks
27 Jun - 29 Jun
In one month
11 Jul - 13 Jul
In two months
8 Aug - 10 Aug

Villas in Ossining

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
Simply Unforgettable 8br, Pool, Pets, Hot Tub, Fire Pit, Private, 1 hr NYC
Exterior

Simply Unforgettable 8br, Pool, Pets, Hot Tub, Fire Pit, Private, 1 hr NYC

10.0 out of 10, Exceptional, (77)
"Beautiful "
Simply Unforgettable 8br, Pool, Pets, Hot Tub, Fire Pit, 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)
"Great place, great host "
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)
"Truly a gem of a place! We loved it. Great spot to celebrate my 30th birthday with a low-key, mellow group. My chef friend who cooked the entire weekend was thrilled at the industrial-style kitchen. The house is probably unlike anything you've ever seen. We're still talking about it haha. A lovely spot. "
The price is SARĀ 3,911
SARĀ 6,440 total
includes taxes & fees
15 Jul - 16 Jul
Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT
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!
Scenic Spring Home With Outdoor Dining Charm
Villa

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!
Interior

Hudson Valley Estate on 4 Acres w/ Private Pool!

3.0 star property
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
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.
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Frequently asked questions

Why book your villa in Ossining with Expedia?
We think vacation time shouldnā€™t be difficult, so if youā€™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 Expediaā€™s helpful filter tool, reserving cheap villas in Ossining couldnā€™t be easier. To find accommodations thatā€™ll make your wallet happy, narrow your search by amenities, star rating and budget.