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.
Hotel Riu Plaza New York Times Square
Manhattan
Save 100% on your flight
Price was $1,332, price is now $738 per person
$738
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.
Seven Beach Lane
Price was $2,750, price is now $1,491 per person
$1,491
per person
Jul 21 - Jul 25
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
This hotel features a restaurant and 2 bars/lounges. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A garden, luggage storage, and concierge services are also on offer.
Hotel Riu Plaza Manhattan Times Square
Manhattan
Save 100% on your flight
Price was $1,333, price is now $738 per person
$738
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
This property features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. A snack bar/deli, dry cleaning, and luggage storage are also on offer.
The Towers at Lotte New York Palace
Manhattan
Price was $2,336, price is now $1,308 per person
$1,308
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
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.
Loews Regency New York Hotel
Manhattan
Save 100% on your flight
Price was $1,648, price is now $957 per person
$957
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
A full-service spa, 2 restaurants, and a gym are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.
Top Southold hotels deals
The Shoals Suites and Slips
61600 Main Rd Southold NY
$243 nightly
The price is $274 total per night
$274 total
May 21 - May 22
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
Vine & Sand
47100 New York 25 Southold NY
$351 nightly
The price is $401 total per night
$401 total
May 11 - May 12
Total with taxes and fees
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.
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Free Cancellation
$91 nightly
The price is $104 total per night
$104 total
May 13 - May 14
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 and barbecue grills are also provided.
Pet friendly
Parking included
Sound View Greenport
58775 County Rd 48 Greenport NY
$326 nightly
The price is $373 total per night
$373 total
May 10 - May 11
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 Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
Free Cancellation
Reserve now, pay when you stay
$145 nightly
The price is $166 total per night
$166 total
May 13 - May 14
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
$264 nightly
The price is $304 total per night
$304 total
May 8 - May 9
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.
Osprey's Dominion
You can enjoy a tasting or tour at Osprey's Dominion during your travels to Southold. Wander the beautiful beaches in this family-friendly area.
Horton Lane Beach
Why not spend a lazy afternoon at Horton Lane Beach during your trip to Southold? Stroll along the beaches or discover the area's sunsets.
Frequently asked questions
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