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.
The Inn At Fox Hollow Hotel
Save 100% on your flight
Price was $964, price is now $530 per person
$530
per person
Dec 14 - Dec 18
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.
NobleDEN Hotel
Manhattan
Price was $2,354, price is now $1,174 per person
$1,174
per person
Dec 21 - Dec 28
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
A restaurant and a rooftop terrace are featured at this hotel. WiFi in public areas is free. A business center, a terrace, and luggage storage are also on offer.
Courtyard New York Manhattan/ Midtown East
Manhattan
Price was $1,759, price is now $880 per person
$880
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. A coffee shop, limo/town car service, and a snack bar/deli are also on offer.
Hotel Riu Plaza Manhattan Times Square
Manhattan
Price was $2,471, price is now $1,294 per person
$1,294
per person
Dec 21 - Dec 28
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
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.
ModernHaus SoHo
Manhattan
Save 100% on your flight
Price was $1,830, price is now $1,021 per person
$1,021
per person
Dec 21 - Dec 28
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. You'll appreciate the seasonal outdoor pool, poolside bar, and rooftop terrace.
Top Southold hotels deals
The Shoals Suites and Slips
61600 Main Rd, Southold, NY
$250 nightly
The price is $283 total per night
$283 total
Nov 4 - Nov 5
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. A business center, a coffee shop, and a communal living room are also on offer.
Free WiFi
Restaurant
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
Free Cancellation
Reserve now, pay when you stay
$82 nightly
The price is $95 total per night
$95 total
Oct 6 - Oct 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 and barbecue grills are also provided.
Pet friendly
Parking included
Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
Free Cancellation
Reserve now, pay when you stay
$94 nightly
The price is $108 total per night
$108 total
Nov 2 - Nov 3
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
Sound View Greenport
58775 County Rd 48, Greenport, NY
$291 nightly
The price is $332 total per night
$332 total
Oct 27 - Oct 28
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
$191 nightly
The price is $218 total per night
$218 total
Oct 6 - Oct 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
Saybrook Point Resort & Marina
2 Bridge St, Old Saybrook, CT
Free Cancellation
Reserve now, pay when you stay
$311 nightly
The price is $357 total per night
$357 total
Nov 5 - Nov 6
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.
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.
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
