Deals on vacations and trips to Southold
Save when you book Southold package deals
Southold flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Alameda Highline
Manhattan
Price was $2,001, price is now $403 per person
$403
per person
Mar 22 - Mar 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Limo/town car service, dry cleaning, and luggage storage are also on offer.
Topping Rose House
Price was $1,167, price is now $551 per person
$551
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
INNSiDE by Meliá New York Nomad
Manhattan
Save 100% on your flight
Price was $800, price is now $414 per person
$414
per person
Mar 19 - Mar 22
found 1 day ago
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 and free WiFi in public areas. A terrace, limo/town car service, and a picnic area are also on offer.
The Inn At Fox Hollow Hotel
Price was $1,104, price is now $618 per person
$618
per person
Apr 9 - Apr 13
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.
1 Hotel Brooklyn Bridge
Save 100% on your flight
Price was $2,268, price is now $1,274 per person
$1,274
per person
Apr 9 - Apr 12
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.
Top Southold hotels deals
The Shoals Suites and Slips
61600 Main Rd Southold NY
$163 nightly
The price is $187 total per night
$187 total
Feb 12 - Feb 13
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
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Free Cancellation
Reserve now, pay when you stay
$244 nightly
The price is $281 total per night
$281 total
Jan 15 - Jan 16
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
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Free Cancellation
Reserve now, pay when you stay
$74 nightly
The price is $85 total per night
$85 total
Jan 15 - Jan 16
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
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
Free Cancellation
Reserve now, pay when you stay
$123 nightly
The price is $140 total per night
$140 total
Jan 22 - Jan 23
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.
Pool
Pet friendly
Hilton Garden Inn Riverhead
2038 Old Country Rd Riverhead NY
Free Cancellation
Reserve now, pay when you stay
$111 nightly
The price is $126 total per night
$126 total
Jan 21 - Jan 22
Total with taxes and fees
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.
Pool
Hot Tub
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.
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.
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
Photos of local treasures
Browse Southold vacation photos for more inspiration
