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Southold Vacations

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

Hotwire can help you find your travel bliss with Southold 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 Southold

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 Southold 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 Southold well.

Southold Flight + Hotel packages

Top Hotel Deals

See all 246 Hotels in Southold
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 ...

Shorecrest Bed and Breakfast

Shorecrest Bed and Breakfast

54300 County Route 48, Southold
4.0 out of 5.0

Situated by the ocean, this bed & breakfast is within 3 mi (5 km) of Horton Point Park, The Old Field Vineyards, and Sparkling Pointe. Kontokosta Winery and ...

Heron Suites at Port of Egypt Marine

Heron Suites at Port of Egypt Marine

61600 Main Rd, Southold
3.5 out of 5.0

Situated near the beach, this condo resort is 0.5 mi (0.8 km) from The Old Field Vineyards and within 3 mi (5 km) of Railroad Museum of Long Island and Sparkling ...

Southold Beach Motel

Southold Beach Motel

53250 North Road, Southold
2.5 out of 5.0

Situated on the beach, this motel is within 3 mi (5 km) of Horton Point Park, The Old Field Vineyards, and Sparkling Pointe. Kontokosta Winery and Railroad Museum ...

Holiday Inn Express Hotel & Suites Long Island-East End

Holiday Inn Express Hotel & Suites Long Island-East End

1707 Old Country Rd, Riverhead
3.0 out of 5.0

Located in the heart of Riverhead, this hotel is within a 10-minute walk of Out East Family Fun and Riverhead Raceway. Tanger Outlet Center and Tanger Outlets ...

$100

$100
Hotel Indigo East End

Hotel Indigo East End

1830 W Main St, Riverhead
4.0 out of 5.0

This family-friendly Riverhead hotel is located in a shopping district, within a 15-minute walk of Tanger Outlets Riverhead and Tanger Outlet Center. Out East ...

$108

$108
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 ...

Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

2038 Old Country Rd, Riverhead
3.5 out of 5.0

Located in the heart of Riverhead, this hotel is within a 15-minute walk of Tanger Outlet Center, Tanger Outlets Riverhead, and Riverhead Raceway. Out East Family ...

$98

$98
Greenview Inn Riverhead

Greenview Inn Riverhead

1433 W Main St, Riverhead
2.5 out of 5.0

Located in the heart of Riverhead, this motel is within 1 mi (2 km) of Tanger Outlets Riverhead and Riverhead Raceway. Tanger Outlet Center and Out East Family ...

$70

$70

Top Flight Deals

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