Southold Vacation Packages 2026 from $1,022

Southold flight + hotel vacation packages

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

Night Hotel Broadway

Manhattan

Save 100% on your flight

$1,022

per person

Sep 21 - Sep 25

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to New York (JFK)

A steam room is featured at this hotel, along with free WiFi in public areas and dry cleaning. There's luggage storage and multilingual staff can provide around-the-clock assistance.

1 Hotel Brooklyn Bridge

$1,633

per person

Oct 9 - Oct 13

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.

Seven Beach Lane

Save 100% on your flight

$1,225

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip flight included

San Juan (SJU) to New York (JFK)

This hotel features a restaurant and 2 bars/lounges. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A garden, luggage storage, and concierge services are also on offer.

1 Hotel Central Park

Manhattan

Save 100% on your flight

$2,655

per person

Nov 3 - Nov 10

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, free WiFi in public areas, and valet parking. A coffee shop, limo/town car service, and a snack bar/deli are also on offer.

NobleDEN Hotel

Manhattan

Save 100% on your flight

$1,074

per person

Oct 11 - Oct 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

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

Top Southold hotels deals

The Shoals Suites and Slips

61600 Main Rd Southold NY

$345 nightly

$391 total

Sep 7 - Sep 8

Total with taxes and fees

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

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Free Cancellation

$87 nightly

$100 total

Aug 23 - Aug 24

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A picnic area is also provided.

Sound View Greenport

58775 County Rd 48 Greenport NY

$343 nightly

$392 total

Sep 15 - Sep 16

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.

The Atlantic Hotel

1655 County Road 39 Southampton NY

$219 nightly

$250 total

Sep 8 - Sep 9

Total with taxes and fees

This hotel's 2 outdoor tennis courts and outdoor pool are among the featured amenities. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking, free newspapers, and barbecue grills are also on offer.

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

Free Cancellation

Reserve now, pay when you stay

$257 nightly

$296 total

Sep 2 - Sep 3

Total with taxes and fees

This smoke-free resort features a private beach, a full-service spa, and 3 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Enjoy the 2 outdoor tennis courts and perks like free valet parking and free WiFi.

On private beach

Pool

North Fork Resort

690 Queen St Greenport NY

$278 nightly

$318 total

Sep 14 - Sep 15

Total with taxes and fees

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this cottage. WiFi in public areas is free. A picnic area and barbecue grills are also provided.

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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.

Stay near popular Southold attractions

Sparkling Pointe

8.8/10 (11 reviews)

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.

See properties

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 $1,022. 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.