Southold Vacations

Hotel options

Hotel stay must be within date range of Leave and Return.

Room 1
*Ages of children at time of trip (for pricing, discounts)


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Your Southold vacation

From family vacations to last-minute romantic getaways, make Orbitz your first and only stop for Southold vacations. You can customize your trip with flights, hotels and activities to match your travel plans and tastes. Sweeten the pot with extra savings when you book your flight and hotel together.

Create your own Southold travel plans
Build your own Southold vacation itinerary. Choose a flight that matches your schedule and a hotel with the amenities you need. Book them together for extra discounts you won't find when booking separately.

Find Southold travel discounts
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Get Southold travel support 24/7
Reach out to an Orbitz travel specialist for Southold vacation assistance. Our specialists are available around the clock at 1-800-504-3248. We can even help with last-minute Southold vacations.

Sign up for free Southold travel alerts
Make travel plans smoother with Orbitz Care Alerts. Receive real-time info about flight delays, weather and other events via phone, e-mail or text. Keep up to six other people in the loop with travel alerts, too.

Scope out your Southold vacation options and savings
With the Orbitz Matrix Display, you can view all your flight and hotel options quickly. Plus, you'll see what you can save on your travel packages when you book them together.

Southold Vacation Packages

Hotel only $109

1 Hyatt Place Long Island East End

4 stars
4.3 / 5 21 reviews


Save 15% on your stay

Guest rooms feature contemporary decor with stylish furnishings including the Hyatt Grand beds, state-of-the-art media and work center with a high-definition 42 inch flat panel television that easily integrates with laptops, a comfortable cozy corner L-shaped... More

Hotel only $159

2 Waters Edge Resort and Spa

3 stars
3.4 / 5 14 reviews

1525 Boston Post Rd Map

The enchanting Waters Edge Resort and Spa is secluded along the beautiful Connecticut shoreline overlooking Long Island Sound in rustic Westbrook. The perfect New England beach front resort offering Charm History Sandy Beaches Spacious Rooms Award Winning Food Luxury Spa... More

Hotel only $102

3 Holiday Inn Express & Suites LONG ISLAND-EAST END

3 stars
3.9 / 5 21 reviews

1707 Old Country Road Map

Enjoy Riverhead Hotel's Convenient Long Island Location Situated in the heart of Long Island's North Fork, the Holiday Inn Express® Hotel East End offers travelers quality accommodations and impeccable service. Minutes from the Long Island Expressway, this Riverhead... More

4 The Blue Inn at North Fork

2 stars
3.8 / 5 6 reviews

7850 Main Road Map

The Blue Inn offers 29 refurbished guest rooms and suites conveniently located on the beautiful and charming North Fork of Long Island New York. Nestled in the heart of wine country The Blue Inn is minutes from unspoiled beaches historic and picturesque villages bustling... More

5 Townsend Manor Inn

3 stars
3.0 / 5 1 reviews

714 Main Street Map

6 Sunset Beach

3 stars
Not yet reviewed

35 Shore Road Map

Sunset Beach is a relaxing hideaway on secluded Shelter Island. The exquisite 20 room seasonal hotel has a charming restaurant and bar where you can take in the stunning sunset views across the picturesque Peconic Bay. Inspired by the Italian and French Rivieras - Sunset... More

Hotel only $107

7 Hilton Garden Inn Riverhead

3 stars
3.9 / 5 18 reviews

2038 Old Country Rd Map

Complimentary wired and Wi-Fi Internet Access

Across the street from famed bargain shopping at the outlets Five minutes from closest Long Island winery, Hilton Garden Inn Riverhead offers a cozy, well-priced place to rest after sipping wine, shopping across the street at Tanger Outlet Mall or sunning on... More

Hotel only $97


3 stars
3.9 / 5 11 reviews

1830 West Main Street, Rt. 25 Map

Enjoy the Best as Long Island, NY Hotel's Guest. A sophisticated palette of cool sea tones and pops of warm orange set the stage for the perfect East End getaway for the Hotel Indigo® East End's guests. The East End of Long Island is the destination of choice for savvy... More

Hotel only $99

9 Comfort Inn Guilford

2 stars
3.6 / 5 7 reviews

300 Boston Post Road Map

Perfect for leisure and business travelers alike. The Comfort Inn of Guilford features free wireless internet service, free breakfast, business center and warmly appointed guestrooms. A number of great dining, shopping and entertainment options are available nearby.... More

Hotel only $59

10 Super 8 Old Saybrook

2 stars
2.9 / 5 15 reviews

37 Spencer Plain Rd. Map

Stay 2, Save 15%

* Free High Speed Wireless Internet * 24 hour desk * Super Start Breakfast * Fax Service * Free Local Calls More

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