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Ossining Vacations

Pack those stellar shades. We have Ossining vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Ossining – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Ossining vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Ossining

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Ossining vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Ossining well.

Top Hotel Deals

See all 171 Hotels in Ossining
Tarrytown House Estate on the Hudson

Tarrytown House Estate on the Hudson

49 E Sunnyside Lane, Tarrytown
4.0 out of 5.0

Situated in the historical district, this hotel is within 1 mi (2 km) of Washington Irving's Sunnyside, Lyndhurst Mansion, and Irvington Town Hall Theater. Memorial ...

$95

$95
Radisson Hotel New Rochelle

Radisson Hotel New Rochelle

1 Radisson Plz, New Rochelle
3.5 out of 5.0

Located near Long Island Sound, this hotel in New Rochelle is 10 miles from Yankee Stadium and 25 miles from downtown New York City.

$118

$118
Hampton Inn & Suites Yonkers

Hampton Inn & Suites Yonkers

160 Corporate Blvd, Yonkers
2.5 out of 5.0

Easily travel to the glamour and bustle of New York City, then retreat to the peaceful luxury of our hotel in the quiet setting of Yonkers, NY. Elegant design ...

$110

$110
The Time Nyack

The Time Nyack

400 High Avenue, Nyack
4.5 out of 5.0

Situated in Nyack, this hotel is within 1 mi (2 km) of Elmwood Playhouse and Memorial Park. Rockland Center for the Arts and Buttermilk Falls Park are also within ...

$103

$103
La Quinta Inn & Suites White Plains - Elmsford

La Quinta Inn & Suites White Plains - Elmsford

540 Saw Mill River Rd, Elmsford
2.5 out of 5.0

Situated in the business district, this hotel is within a 5-minute walk of Captain Lawrence Brewing Company and Sportime USA. Westchester Skating Academy and ...

$81

$81
Hyatt Regency Greenwich

Hyatt Regency Greenwich

1800 E Putnam Avenue, Old Greenwich
4.5 out of 5.0

This Hyatt Regency hotel, located on the Stamford/Greenwich border, is minutes from both the heart of downtown Stamford and shopping on Greenwich Avenue. New ...

$98

$98
DoubleTree by Hilton Tarrytown

DoubleTree by Hilton Tarrytown

455 S Broadway, Tarrytown
4.0 out of 5.0

Situated in the historical district, this spa hotel is within 1 mi (2 km) of Lyndhurst Mansion and Tarrytown Music Hall. Washington Irving's Sunnyside and Pierson ...

$104

$104
Crowne Plaza White Plains - Downtown

Crowne Plaza White Plains - Downtown

66 Hale Ave, White Plains
4.5 out of 5.0

Located in the heart of White Plains, this eco-friendly hotel is within 1 mi (2 km) of The Westchester Mall, Pace University Law School, and Galleria at White ...

$119

$119
Royal Regency Hotel

Royal Regency Hotel

165 Tuckahoe Rd, Yonkers
4.0 out of 5.0

Situated in the business district, this hotel is 2.5 mi (4.1 km) from Hudson River Museum and 2.6 mi (4.1 km) from Sarah Lawrence College. Tibbetts Brook Park ...

$102

$102
Americas Best Value Inn

Americas Best Value Inn

1209 E Main St, Stamford
2.5 out of 5.0

Situated near the beach, this hotel is within 1 mi (2 km) of Chelsea Piers and Cove Island Park. Stamford Town Center and Stamford Public Library - Ferguson ...

$64

$64

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.