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Greenport Vacations

Pack those stellar shades. We have Greenport 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 Greenport – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Greenport 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 Greenport

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 Greenport 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 Greenport well.

Greenport Flight + Hotel packages

Top Hotel Deals

See all 226 Hotels in Greenport
American Beech Hotel

American Beech Hotel

300 Main Street, Greenport
4.0 out of 5.0

Situated by the sea, this inn is within a 5-minute walk of Greenport Farmers' Market and Camera Obscura. East End Seaport Maritime Museum and Railroad Museum ...

$149

$149
Sound View Greenport

Sound View Greenport

58775 Route 48, Greenport
3.5 out of 5.0

Situated in Greenport, this hotel is within 3 mi (5 km) of Kontokosta Winery, Railroad Museum of Long Island, and Camera Obscura. East End Seaport Maritime Museum ...

$140

$140
Cliffside Resort Condominiums

Cliffside Resort Condominiums

61475 Route 48 (North Road), Greenport
3.5 out of 5.0

Offering direct access to the beach, this Greenport condo building is within 3 mi (5 km) of Kontokosta Winery, Island's End Golf and Country Club, and Railroad ...

$174

$174
Stirling House Bed & Breakfast

Stirling House Bed & Breakfast

104 Bay Avenue, Greenport
3.5 out of 5.0

Situated on the waterfront, this bed & breakfast is within a 15-minute walk of East End Seaport Maritime Museum and Railroad Museum of Long Island. Kontokosta ...

$255

$255
Fordham House

Fordham House

817 Main Street, Greenport
3.0 out of 5.0

Situated in Greenport, this bed & breakfast is within a 15-minute walk of Greenport Farmers' Market, Kontokosta Winery, and Camera Obscura. East End Seaport ...

The Gallery Hotel

The Gallery Hotel

439 Main Street, Greenport
4.0 out of 5.0

Situated in Greenport, this boutique hotel is within a 10-minute walk of Greenport Farmers' Market, Camera Obscura, and East End Seaport Maritime Museum. Railroad ...

Harbor Knoll Bed & Breakfast

Harbor Knoll Bed & Breakfast

424 4th Street, Greenport
Hyatt Place Long Island East End

Hyatt Place Long Island East End

451 East Main Street, Riverhead
3.5 out of 5.0

Located in central Riverhead, Hyatt Place Long Island East End overlooks the Peconic River. It's next to Long Island Aquarium & Exhibition Center and Treasure ...

$108

$108
Southampton Inn

Southampton Inn

91 Hill Street, Southampton
3.5 out of 5.0

This family-friendly Southampton hotel is located by the ocean, within a 5-minute walk of Agawam Park and Southampton Cultural Center. Southampton Historical ...

$160

$160
Saybrook Point Inn, Marina and Spa

Saybrook Point Inn, Marina and Spa

2 Bridge St, Old Saybrook
4.0 out of 5.0

Situated on the waterfront, this spa hotel is 1.5 mi (2.4 km) from General William Hart House and 1.7 mi (2.7 km) from Katharine Hepburn Cultural Arts Center. ...

$233

$233

Top Flight Deals

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