Deals on vacations and trips to Southold

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Southold flight + hotel vacation packages

The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Manhattan
Save 100% on your flight
per person
May 25 - May 28
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, express check-in, and valet parking. Self parking, a coffee shop, and a snack bar/deli are also offered.
The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
per person
Jun 27 - Jun 30
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
This hotel features a restaurant, a gym, and a bar/lounge. Families will appreciate the onsite laundry facilities and in-room childcare. Guests will appreciate perks like free WiFi and a free area shuttle.
Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Save 100% on your flight
per person
Jun 7 - Jun 9
Roundtrip non-stop flight included
Atlanta (ATL) to New York (JFK)
A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. A coffee shop, limo/town car service, and a snack bar/deli are also on offer.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
May 24 - May 28
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.
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Jun 5 - Jun 9
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.
Prices and availability subject to change. Additional terms may apply.

Top Southold hotels deals

The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd, Southold, NY
The price is $259 per night
$259
per night
Apr 21 - Apr 22
A restaurant and a bar/lounge are featured at this hotel. Enjoy the free continental breakfast each morning. A business center, a coffee shop, and a communal living room are also on offer.
Breakfast included
Restaurant
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

3 out of 5
2038 Old Country Rd, Riverhead, NY
Free Cancellation
Reserve now, pay when you stay
The price is $115 per night
$115
per night
Apr 28 - Apr 29
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the indoor pool and perks like free self parking and free WiFi. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Hot Tub
Pet friendly
Residence Inn by Marriott New York Long Island East End

Residence Inn by Marriott New York Long Island East End

3 out of 5
2012 Old Country Road, Riverhead, NY
Free Cancellation
Reserve now, pay when you stay
The price is $134 per night
$134
per night
Apr 22 - Apr 23
2 spa tubs, an outdoor pool, and an indoor pool 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. Enjoy the 24-hour gym and free perks like full breakfast and free self parking.
Hot Tub
Pet friendly
Hyatt Place Long Island East End

Hyatt Place Long Island East End

3 out of 5
451 East Main Street, Riverhead, NY
Free Cancellation
The price is $134 per night
$134
per night
Apr 28 - Apr 29
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.
Pet friendly
Breakfast available
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
Free Cancellation
Reserve now, pay when you stay
The price is $253 per night
$253
per night
Apr 28 - Apr 29
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 business center, free WiFi in public areas, 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.
Hot Tub
Pet friendly
Sag Harbor Inn

Sag Harbor Inn

3.5 out of 5
45 West Water Street, Sag Harbor, NY
The price is $209 per night
$209
per night
Apr 21 - Apr 22
An outdoor pool is featured at this hotel, along with free self parking. Enjoy the free continental breakfast each morning. A fireplace in the lobby and luggage storage are also provided.
Breakfast included
Pool
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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

Image for Sparkling Pointe

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.

Sparkling Pointe
Image for Croteaux Vineyards

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.

Croteaux Vineyards
Image for Sannino's Bella Vita Vineyard

Sannino's Bella Vita Vineyard

You can enjoy a tasting or tour at Sannino's Bella Vita Vineyard during your travels to Southold. Wander the beaches or discover the sunsets in this family-friendly area.

Sannino's Bella Vita Vineyard

Frequently asked questions

How much are vacation packages to Southold?
With vacation packages being sold for only $501, there’s no need to drain your bank balance for your visit to Southold. Travelocity can help. Bundle experiences, flights and hotels into a package and receive some fantastic discounts. The more you book, the more you save.
Where can I get the best vacation package deals for Southold?
You can snap up sensational Southold package deals with Travelocity. Select from 400 airlines and 1,000,000 worldwide properties and turn those travel dreams into reality.
Why should I book my Southold vacation package via Travelocity?
Whether you’re searching for the ultimate unplugged getaway or you crave the fun and excitement of the big smoke, booking everything with Travelocity saves you time, hassle and money. No need to sift through hundreds of different websites for the best deal — our Price Match Guarantee ensures you’ll never be out of pocket, and our professional customer service experts are available 24/7 should you need them.
Can I save money on my Southold car rental if I book it with a hotel or flight?
Combining your bookings into a Southold vacation package will leave you with some serious savings. You can book a flight and car; a car, hotel and flight; or a car and hotel. You won’t find a better way to explore the greater Southold area than from behind the wheel of your own rental car. You can also add tours and experiences to your Travelocity package.
What is the best time of year to go to Southold?
Escape in and spend more cash on amazing experiences, rather than your hotel. This is the most inexpensive month to arrange your stay. Prices are at their most expensive in , so avoid this time if you want to save. May, June and July are the busiest months in Southold. You’ll need to book well in advance and be ready to pay higher prices. January, October and December are the least popular months to visit.