Photo by Linda Zanetti

Search Villas 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

Compare 8 Villas in Ossining with updated reviews, rates, and availability.

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

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

10.0 out of 10, Exceptional, (21)
"Our family went to the Hudson Valley area for a wedding. Pre stay communication with Malka was excellent and we all had a wonderful time. Lots of room for the kids to play and be entertained downstairs as well as upstairs in the Projection Room. The backyard was a great soccer area and the fire pit was great to sit around at night. Firewood on site was a real plus! I do recommend to anyone doing substantial cooking for many people to bring their own favorite pots and pans if possible though...
Kick back & relax in this peaceful, stylish place to stay with the whole family.
DREAM Home, Pool, Hot Tub, Game Rm & Mountains.

DREAM Home, Pool, Hot Tub, Game Rm & Mountains.

10.0 out of 10, Exceptional, (1)
"This house was absolutely perfect for our friend's weekend wedding. 14 guests, guys/girls in their early to mid 30s. We stayed at this house and attended our friend's rehearsal dinner and wedding about 30 min away. The location is perfect, slightly secluded and quiet. The property is very large and has all the amenities a group of people could want. The interior of the house was clean, setup nicely, and aesthetically pleasing. Everything listed was accurate. The pool and hot tub were clean and...
DREAM Home, Pool, Hot Tub, Game Rm & Mountains.
Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT
Exterior

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

8.6 out of 10, Excellent, (4)
"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)."
The price is AED 2,700
AED 4,763 total
includes taxes & fees
5 Jan - 6 January 2025
Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT
5 Bdrm luxury near west point with gym, game room and more

5 Bdrm luxury near west point with gym, game room and more

3.0 star property
5 Bdrm luxury near west point with gym, game room and more
Historic Castle 1876 13 Mins to Wing Foot cc border of GREENWICH and New York
Point of interest

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
Exterior

NYC Hidden Chatteau

NYC Hidden Chatteau
Hudson Valley Estate on 4 Acres w/ Private Pool!
Living area

Hudson Valley Estate on 4 Acres w/ Private Pool!

3.0 star property
Hudson Valley Estate on 4 Acres w/ Private Pool!
Hudson Valley Estate on 4 Acres w/ Private Pool!
Nyack Vacation Rental | 7BR | 4.5BA | 5,400 Sq Ft | Stairs Required

Hudson Valley Estate on 4 Acres w/ Private Pool!

Hudson Valley Estate on 4 Acres w/ Private Pool!
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
Property amenity

Stamford Suites

2.5 star property
6.8 out of 10, (772)
"It was in walking distance of the event we were going to."
The price is AED 515
AED 592 total
includes taxes & fees
3 Jan - 4 January 2025
Stamford Suites
Waterfront Retreat Center for Health & Wellness
Exterior

Waterfront Retreat Center for Health & Wellness

9.6 out of 10, Exceptional, (54)
"Second time our 24 person family group stayed here, and if anything, it was even better than last year! The location is exceptional, a quiet, private beautiful Victorian era house right on the Sound. The house is roomy, immaculate and very well equipped. Nancy is on top of everything and responds essentially immediately to any and every concern. There aren’t enough superlatives to describe our wonderful experience! "
Waterfront Retreat Center for Health & Wellness
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Autumn Foliage - Private Patio View

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (105)
"Super cozy apartment with a beautiful view. Very welcoming host and a great place for a short stay near Bear Mountain. "
The price is AED 617
AED 915 total
includes taxes & fees
28 Dec - 29 Dec
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.

Frequently asked questions

Why book your villa in Ossining with Expedia?
We think organizing a vacation shouldn’t be hard, so if you’re looking for villas at the right price, Expedia can help. Save money and go for an all-inclusive stay, or splurge on a high-end villa to treat your sweetheart. Use our convenient search filters to find an escape in Ossining that you’ll adore.
How can I find cheap villas in Ossining?
With Expedia’s user-friendly filter tool, scoring cheap villas in Ossining couldn’t be simpler. To find stays that’ll make your wallet happy, narrow your search by budget, amenities and star rating.