Southold Vacation Packages 2025 from $773

Southold flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

INNSiDE by Meliá New York Nomad

Manhattan

per person

Aug 22 - Aug 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A terrace, limo/town car service, and a picnic area are also on offer.

NobleDEN Hotel

Manhattan

per person

Aug 22 - Aug 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

A restaurant and a rooftop terrace are featured at this hotel. WiFi in public areas is free. A business center, a terrace, and luggage storage are also on offer.

1 Hotel Brooklyn Bridge

per person

Aug 30 - Sep 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

A full-service spa, a gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the seasonal outdoor pool and visit the 2 bars/lounges and poolside bar for drinks.

Ruschmeyers Hotel

Save 100% on your flight

per person

Sep 4 - Sep 7

found 1 day ago

Roundtrip flight included

Dallas (DFW) to New York (JFK)

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, express check-in, and express check-out are also on offer.

The Shelburne Sonesta New York

Manhattan

Save 100% on your flight

per person

Aug 21 - Aug 25

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, laundry service, and valet parking. WiFi in public areas, luggage storage, and laundry facilities are also on offer.

Top Southold hotels deals

The Shoals Suites and Slips

61600 Main Rd, Southold, NY

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A restaurant and a bar/lounge are featured at this hotel. A business center, a coffee shop, and a communal living room are also on offer.

Free WiFi

Restaurant

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd, Old Saybrook, CT

Free Cancellation

Reserve now, pay when you stay

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This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area and barbecue grills are also provided.

Pet friendly

Parking included

Baron's Cove

31 West Water Street, Sag Harbor, NY

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This hotel features a restaurant, a gym, and a bar/lounge. Enjoy the seasonal outdoor pool and perks like free valet parking and free WiFi. Free self parking, a business center, and a coffee shop are also offered.

Pool

Spa

Saybrook Point Resort & Marina

2 Bridge St, Old Saybrook, CT

Free Cancellation

Reserve now, pay when you stay

Get rates

A full-service spa, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and free train station pick-up. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and a shopping center shuttle.

Pool

Hot Tub

Hyatt Place Long Island East End

451 East Main Street, Riverhead, NY

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A marina, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at one of the 2 bars/lounges and enjoy perks like free self parking.

Pool

Pet friendly

Greenporter Hotel

326 Front St, Greenport, NY

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This hotel features a 24-hour gym and a seasonal outdoor pool. Enjoy the hot tub and perks like free self parking and free WiFi. A business center, a garden, and express check-out are also on offer.

Pool

Hot Tub

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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.

Popular places to visit

Cleanest, prettiest winery on the east end of Long Island! Try the Cuvee' Rose!

Sparkling Pointe

You can enjoy a tasting or tour at Sparkling Pointe during your travels to Southold. Discover the sunsets and wineries in this family-friendly area.

Croteaux Vineyards

You can enjoy a tasting or tour at Croteaux Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

Osprey's Dominion

You can enjoy a tasting or tour at Osprey's Dominion during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

Frequently asked questions

How much are vacation packages to Southold?

With a Travelocity vacation package, you could paint the town red in Southold for only $773. Activities, flights and hotels --- we've got you. You'll save loads just by bundling together your bookings. And with all of that taken care of before you even set off, you don't have to worry about a thing.

Where can I get the best vacation package deals for Southold?

No matter what you enjoy doing, Travelocity can help you score the perfect Southold package deal. All you have to do is mix and match from our 400 air carriers and 1,000,000 properties around the world.

Why should I purchase my Southold vacation bundle with Travelocity?

Because life is one incredible journey, and we offer everything you could hope for to help you along the way. With our top-quality service and Price Match Guarantee, you can book with confidence. Plus, you can sleep easy while you're on the road knowing you can reach us with our 24/7 support.

Can I save on my Southold car rental if I book it with a hotel or flight?

You can with our Southold vacation packages. With one of these, there are tons of ways to stretch your travel budget further. Combine any two or more car, hotel, flight and tour bookings and watch your savings start to grow. With your own set of wheels, all the popular attractions around Southold are an unforgettable road trip away.