Deals on vacations and trips to Town of Southold Town

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Beautiful spot on the #longisland sound surfing

Greenport

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Greenport

Town of Southold Town flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $728, price is now $381 per person
$381
per person
Nov 4 - Nov 7
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.
Harpoon House

Harpoon House

3 out of 5
Price was $941, price is now $494 per person
$494
per person
Oct 20 - Oct 24
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This bed & breakfast features a restaurant and 3 bars/lounges. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a terrace, and a garden are also on offer.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $2,262, price is now $1,236 per person
$1,236
per person
Oct 26 - Oct 29
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.
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
Save 100% on your flight
Price was $922, price is now $530 per person
$530
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
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.
Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Save 100% on your flight
Price was $688, price is now $407 per person
$407
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Free WiFi in public areas, a library, and luggage storage are available at this hotel. Multilingual staff at the 24-hour front desk can provide around-the-clock assistance.

Top Town of Southold Town hotels deals

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
$332 nightly
The price is $380 total per night
$380 total
Sep 9 - Sep 10
Total includes 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
Greenporter Hotel

Greenporter Hotel

2 out of 5
326 Front St, Greenport, NY
$151 nightly
The price is $173 total per night
$173 total
Sep 2 - Sep 3
Total includes taxes and fees
This hotel features a 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
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St, Greenport, NY
$262 nightly
The price is $299 total per night
$299 total
Sep 7 - Sep 8
Total includes 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

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd, Southold, NY
$393 nightly
The price is $446 total per night
$446 total
Sep 8 - Sep 9
Total includes taxes and fees
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
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

4 out of 5
1400 Silvermere Rd, Greenport, NY
$356 nightly
The price is $406 total per night
$406 total
Sep 2 - Sep 3
Total includes taxes and fees
This smoke-free hotel features a private beach and 2 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
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road), Greenport, NY
$370 nightly
The price is $422 total per night
$422 total
Sep 11 - Sep 12
Total includes taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A terrace, a picnic area, and barbecue grills are also on offer.
Pool
Kitchen
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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

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Town of Southold Town
Town of Southold Town
Photo by Jan Shannon
Photo by Jan Shannon
Photo by Richard Miska
Photo by Richard Miska
Photo by Dawn Biscardi Alperstein
Photo by Dawn Biscardi Alperstein

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 $381. 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.