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.
Radio Hotel
Manhattan
Save 100% on your flight
Price was $670, price is now $432 per person
$432
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the express check-out and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
1 Hotel Brooklyn Bridge
Save 100% on your flight
Price was $2,841, price is now $1,557 per person
$1,557
per person
Aug 2 - Aug 6
found 1 day 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.
Lotte New York Palace
Manhattan
Save 100% on your flight
Price was $2,286, price is now $1,451 per person
$1,451
per person
Sep 10 - Sep 15
found 1 day 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.
Night Hotel Broadway
Manhattan
Price was $1,265, price is now $839 per person
$839
per person
Aug 25 - Aug 30
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Newark Liberty Intl. Airport (EWR)
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.
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 30 - Jul 1
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.
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Free Cancellation
$102 nightly
The price is $117 total per night
$117 total
Jul 6 - Jul 7
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
$525 nightly
The price is $600 total per night
$600 total
Jun 25 - Jun 26
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 Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
Free Cancellation
Reserve now, pay when you stay
$417 nightly
The price is $476 total per night
$476 total
Jun 30 - Jul 1
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
$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
The Atlantic Hotel
1655 County Road 39 Southampton NY
$251 nightly
The price is $287 total per night
$287 total
Jun 25 - Jun 26
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.
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.
Frequently asked questions
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