Deals on vacations and trips to Southold
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Southold flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel
Save 100% on your flight
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.
Sound View Greenport
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
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.
1 Hotel Brooklyn Bridge
Save 100% on your flight
per person
Sep 21 - Sep 23
found 15 hours 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
Save 100% on your flight
per person
Oct 12 - Oct 17
found 19 hours 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.
Empire Hotel
Manhattan
Save 100% on your flight
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This boutique hotel features 3 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. There's a seasonal outdoor pool on site, and a 24-hour front desk and a coffee shop are also provided.
Top Southold hotels deals
The Shoals Suites and Slips
61600 Main Rd, Southold, NY
$397 nightly
The price is $450 total per night
$450 total
Sep 3 - Sep 4
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
Vine & Sand
47100 New York 25, Southold, NY
A seasonal outdoor pool is featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. A terrace, a garden, and a lobby fireplace are also on offer.
Pool
Breakfast included
Greenview Inn Riverhead
1433 W Main St, Riverhead, NY
Free Cancellation
Reserve now, pay when you stay
$104 nightly
The price is $119 total per night
$119 total
Aug 19 - Aug 20
Total includes taxes and fees
Free self parking is available and the motel's front desk is staffed around-the-clock. WiFi in public areas is free. A garden is also provided.
Parking included
Free WiFi
Sound View Greenport
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
Saybrook Point Resort & Marina
2 Bridge St, Old Saybrook, CT
Free Cancellation
Reserve now, pay when you stay
$419 nightly
The price is $479 total per night
$479 total
Aug 26 - Aug 27
Total includes taxes and fees
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
The Atlantic Hotel
1655 County Road 39, Southampton, NY
$501 nightly
The price is $572 total per night
$572 total
Aug 18 - Aug 19
Total includes taxes and fees
This hotel's 2 outdoor tennis courts and outdoor pool are among the featured amenities. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
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
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.
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.
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.
Frequently asked questions
Photos of local treasures
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