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.
Lotte New York Palace
Manhattan
Save 100% on your flight
Price was $2,121, price is now $1,286 per person
$1,286
per person
Sep 10 - Sep 15
found 15 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Topping Rose House
Price was $6,631, price is now $3,831 per person
$3,831
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Mandarin Oriental, New York
Manhattan
Save 100% on your flight
Price was $5,997, price is now $3,522 per person
$3,522
per person
Aug 30 - Sep 5
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Make the most of the indoor pool and gym, and relax with drinks at one of the 2 bars/lounges.
1 Hotel Brooklyn Bridge
Save 100% on your flight
Price was $3,834, price is now $2,288 per person
$2,288
per person
Jul 30 - Aug 4
found 20 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Top Southold hotels deals
The Shoals Suites and Slips
61600 Main Rd Southold NY
$381 nightly
The price is $431 total per night
$431 total
Jun 23 - Jun 24
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
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Free Cancellation
$109 nightly
The price is $126 total per night
$126 total
Jun 23 - Jun 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
$500 nightly
The price is $571 total per night
$571 total
Jul 1 - Jul 2
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 Atlantic Hotel
1655 County Road 39 Southampton NY
$264 nightly
The price is $302 total per night
$302 total
Jul 6 - Jul 7
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.
Pool
Pet friendly
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
Free Cancellation
Reserve now, pay when you stay
$408 nightly
The price is $466 total per night
$466 total
Jun 28 - Jun 29
Total with taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. 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. There's a garden and multilingual staff can provide around-the-clock assistance.
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Free Cancellation
Reserve now, pay when you stay
$364 nightly
The price is $419 total per night
$419 total
Jun 30 - Jul 1
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
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.
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.
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.
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