Town of Southold Town Vacation Packages 2026 from $348

Search vacation packages deals in Town of Southold Town's top destinations

The one of best destinations for summer vacation!#Trove#Summer

Greenport

Vacations

Town of Southold Town flight + hotel vacation packages

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

Topping Rose House

$348

per person

Mar 6 - Mar 8

found 12 hours ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and free valet parking. Enjoy the gym and perks like free self parking and a free area shuttle.

Lotte New York Palace

Manhattan

$1,184

per person

Apr 5 - Apr 10

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 smoke-free hotel. Families will appreciate complimentary bicycles and babysitting. Traveling on business? Take advantage of the business center, express check-out, and valet parking.

1 Hotel Brooklyn Bridge

$1,615

per person

Apr 10 - Apr 14

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.

Beechmont - Perfect for Family Retreat!

North End

Save 100% on your flight

$976

per person

Mar 12 - Mar 15

found 1 day ago

Roundtrip flight included

Dallas (DFW) to New Haven (HVN)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.

The Inn At Fox Hollow Hotel

Save 100% on your flight

$498

per person

Feb 27 - Mar 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free train station pick-up. Enjoy the 24-hour gym and perks like free self parking and a free area shuttle.

Top Town of Southold Town hotels deals

Sound View Greenport

58775 County Rd 48 Greenport NY

$159 nightly

$182 total

Jan 28 - Jan 29

Total with taxes and fees

A private beach and a restaurant are featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like continental breakfast and WiFi in public areas.

On private beach

Pool

The Harbor Front Inn

209 Front St Greenport NY

$142 nightly

$162 total

Jan 28 - Jan 29

Total with taxes and fees

This hotel features a 24-hour gym and a seasonal outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free continental breakfast each morning.

Pool

Breakfast included

The Shoals Suites and Slips

61600 Main Rd Southold NY

$158 nightly

$181 total

Jan 29 - Jan 30

Total with taxes and fees

This hotel features a bar/lounge, a coffee shop, and a communal living room. A business center, a picnic area, and express check-out are also on offer.

Free WiFi

Air conditioning

Silver Sands Motel & Beach Bungalows

1400 Silvermere Rd Greenport NY

$275 nightly

$314 total

Jan 30 - Jan 31

Total with taxes and fees

This smoke-free hotel features a private beach, a full-service spa, and 3 restaurants. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.

On private beach

Spa

Zey Hotel

439 Main Street Greenport NY

$225 nightly

$259 total

Jan 28 - Jan 29

Total with taxes and fees

A bar/lounge and a coffee shop are featured at this hotel, along with free self parking. WiFi in public areas is free. A terrace, a garden, and a picnic area are also on offer.

Pet friendly

Parking included

The Menhaden

207 Front St Greenport NY

$282 nightly

$317 total

Feb 25 - Feb 26

Total with taxes and fees

This hotel features a restaurant, a rooftop terrace, and a bar/lounge. Guests will appreciate free perks like self-serve breakfast and WiFi in public areas. A coffee shop, a terrace, and a snack bar/deli are also on offer.

Breakfast included

Pet friendly

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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.

Photos of local treasures

Browse Town of Southold Town vacation photos for more inspiration

Horton Point Lighthouse, the landmark navigational architecture built in 1857 commissioned by George Washington, on Long Island, Southold, New York, USA

Plum Island on the northern coast of MA is the perfect place to end your morning run. The views 🙌🏽 #LifeAtExpedia

Beautiful spot on the #longisland sound surfing

Frequently asked questions

How much are vacation packages to Town of Southold Town?

Spoil yourself with an unforgettable travel experience in Town of Southold Town with a vacation package starting at $348. Locking in flights, tours and hotels through Travelocity is simple. And even better, our great deals will leave you with more savings in your pocket for plenty of fun times.

How long should my Town of Southold Town vacation be?

Around 2 nights is the average amount of time travelers vacation in Town of Southold Town. But the perfect trip length depends on how many cherished memories you want to make. Why not stay a little longer and explore some off-the-beaten-path gems?

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

Travelocity has all you need to score an awesome Town of Southold Town package deal. Choose from 400 partner airlines and 1,000,000 properties all over the globe and create a travel itinerary that's perfect for you. With this amount of choice, you have inspiration galore for your next big adventure.

Why should I purchase my Town of Southold Town vacation bundle with Travelocity?

We offer 24/7 customer support, exceptional service and a Price Match Guarantee. Life is all about the journey — and we have amazing destinations for you to journey to all across the globe. Explore with us and your bank balance will thank you for it.

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

Combining your car, flight and hotel into a Town of Southold Town vacation package is an easy way to land the best deal. Plus, having your own rental car gives you total freedom to find your way to all those amazing sights you'd like to check out. Sitting 85 mi away from Town of Southold Town, Times Square is one place that should be on your itinerary. Buckle up and make a day trip of it.

Which airport is best for Town of Southold Town?

Bradley Intl. Airport (BDL) is 60 mi from the city center and is the starting point for many memorable experiences. Alternatively, MacArthur Airport (ISP) is 40 mi away from central Town of Southold Town and Tweed - New Haven Regional Airport (HVN) is 30 mi away from central Town of Southold Town.

What is there to do in Town of Southold Town?

There's a certain magic in the air as you stroll through the streets of Town of Southold Town. 67 Steps Beach and Greenport Carousel are just two attractions that make this city so popular, so add them to your to-do list.

Where should I stay when visiting Town of Southold Town?

Many people choose to check in to the The Blue Inn At North Fork. It's a great base for your Town of Southold Town vacation.