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.
Radio Hotel
Manhattan
Price was $627, price is now $287 per person
$287
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Valet parking, a coffee shop, and a snack bar/deli are also offered.
Hotel Seville Nomad, in the Unbound Collection by Hyatt
Manhattan
Price was $809, price is now $350 per person
$350
per person
Feb 5 - Feb 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A computer station, dry cleaning, and luggage storage are also on offer.
INNSiDE by Meliá New York Nomad
Manhattan
Price was $1,105, price is now $500 per person
$500
per person
Feb 5 - Feb 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
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.
Sheraton New York Times Square Hotel
Manhattan
Price was $798, price is now $369 per person
$369
per person
Feb 5 - Feb 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a snack bar/deli are also offered.
Hotel Riu Plaza New York Times Square
Manhattan
Price was $1,207, price is now $575 per person
$575
per person
Feb 19 - Feb 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
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.
Top Southold hotels deals
The Shoals Suites and Slips
61600 Main Rd Southold NY
$174 nightly
The price is $199 total per night
$199 total
Dec 29 - Dec 30
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 luggage storage are also on offer.
Free WiFi
Air conditioning
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Free Cancellation
Reserve now, pay when you stay
$71 nightly
The price is $82 total per night
$82 total
Dec 11 - Dec 12
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
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Free Cancellation
Reserve now, pay when you stay
$175 nightly
The price is $202 total per night
$202 total
Nov 30 - Dec 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
Sound View Greenport
58775 County Rd 48 Greenport NY
$203 nightly
The price is $232 total per night
$232 total
Nov 30 - Dec 1
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
Quality Inn Old Saybrook - Westbrook
100 Essex Rd Old Saybrook CT
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $116 total per night
$116 total
Dec 7 - Dec 8
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.
Pool
Breakfast included
Saybrook Point Resort & Marina
2 Bridge St Old Saybrook CT
Free Cancellation
Reserve now, pay when you stay
$256 nightly
The price is $295 total per night
$295 total
Nov 30 - Dec 1
Total with 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
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.
The Old Field Vineyards
You can enjoy a tasting or tour at The Old Field Vineyards during your travels to Southold. Stroll along 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
Browse Southold vacation photos for more inspiration
