Book Holiday Homes in Ossining

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Featured Holiday Homes in Ossining

Cozy Indoor Hot Tub, Fire Pit & Game Room

Cozy Indoor Hot Tub, Fire Pit & Game Room

Suffern
Located in Suffern, this vacation home is within a 5-minute drive of Lower Hudson Valley Challenger Learning Center and Good Samaritan Hospital - Suffern.
Cozy Indoor Hot Tub, Fire Pit & Game Room
Waterfront Retreat Center for Health & Wellness

Waterfront Retreat Center for Health & Wellness

New Rochelle
Located in New Rochelle, this vacation home is by the ocean, within a 5-minute drive of New Roc City and Monroe College New Rochelle Campus.
Waterfront Retreat Center for Health & Wellness
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Stamford
With a stay at this vacation home in Stamford (North Stamford), you'll be a 4-minute drive from Mianus River State Park and 5 minutes from Yale New Haven Health ...
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
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Cozy and beautiful house

Cozy and beautiful house

Mount Vernon
With a stay at this vacation home in Bronxville (North Side), you'll be within a 15-minute drive of Fordham University and Bronx Zoo.
Cozy and beautiful house
Historic Hideaway with Lake Access!

Historic Hideaway with Lake Access!

South Salem
With a stay at this vacation home in South Salem, you'll be within a 10-minute drive of Four winds and Aldrich Contemporary Art Museum.
Historic Hideaway with Lake Access!
Bright Cornwall-On-Hudson Vacation Rental!

Bright Cornwall-On-Hudson Vacation Rental!

Cornwall-On-Hudson
With a stay at this vacation home in Cornwall, you'll be in the mountains, within a 10-minute drive of United States Military Academy and New York Military ...
Bright Cornwall-On-Hudson Vacation Rental!
Up-to-date Home w/ Pool, Playground & Fireplace!

Up-to-date Home w/ Pool, Playground & Fireplace!

Suffern
Located in Suffern, this vacation home is within a 5-minute drive of Lower Hudson Valley Challenger Learning Center and Good Samaritan Hospital - Suffern.
Up-to-date Home w/ Pool, Playground & Fireplace!
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!

'The Glabin’: Garrison Gem w/ Deck & Fire Pit!

Garrison
Located in Philipstown, this vacation home is in the mountains, a 4-minute drive from Graymoor - The Holy Mountain and 9 minutes from Peekskill Landing ...
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point

Highland Falls
With a stay at this vacation home in Highland Falls, you'll be within a 10-minute walk of United States Military Academy and West Point Museum.
Updated Home w/ Patio Half Mile to West Point
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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.

Ossining Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Ossining vacation homes are the perfect way for you to wing it.

Holiday houses in Ossining let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Ossining in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Ossining adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Ossining with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Ossining vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Ossining Holiday Homes essential information

Accommodation
262 Holiday Homes
Lowest Price
AU$100
Highest Price
AU$349
Popular accommodation
Cozy Indoor Hot Tub, Fire Pit & Game Room, Waterfront Retreat Center for Health & Wellness, Bright Stylish Chic 4BR 4BA Home Pet Friendly!, Cozy and beautiful house , Historic Hideaway with Lake Access!, Bright Cornwall-On-Hudson Vacation Rental!, Up-to-date Home w/ Pool, Playground & Fireplace!, 'The Glabin’: Garrison Gem w/ Deck & Fire Pit!, Updated Home w/ Patio Half Mile to West Point

Top trending hotels in Ossining

Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303, Orangeburg, NY
Fully refundableReserve now, pay when you stay
The price is AU$100 per night from 20 Feb to 21 Feb
AU$100
includes taxes & fees
20 Feb - 21 Feb
With a stay at Armoni Inn & Suites in Orangeburg, you'll be within a 15-minute walk of Dominican College and St. Thomas Aquinas College.
Armoni Inn & Suites
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
The price is AU$212 per night from 23 Feb to 24 Feb
AU$212
includes taxes & fees
23 Feb - 24 Feb
With a stay at Royal Regency Hotel in Yonkers (Northwest Yonkers), you'll be within a 15-minute drive of Columbia University and Yankee Stadium.
Royal Regency Hotel
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave, White Plains, NY
Fully refundableReserve now, pay when you stay
The price is AU$349 per night from 2 Mar to 3 Mar
AU$349
includes taxes & fees
2 Mar - 3 Mar
In the heart of White Plains, Sonesta White Plains Downtown is within a 5-minute drive of The Westchester Mall and Westchester County Center.
Sonesta White Plains Downtown
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Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is AU$252 per night from 13 Feb to 14 Feb
AU$252
includes taxes & fees
13 Feb - 14 Feb
With a stay at Hampton Inn White Plains/Tarrytown in Elmsford, you'll be in the historical district, within a 5-minute drive of Westchester County Center and ...
Hampton Inn White Plains/Tarrytown
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See all available properties in Ossining
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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.

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^Subject to availability and chosen travel dates.