Southold Vacation Packages
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Top Southold vacation package deals
Price found within the past 48 hours. Click for updated prices.
4.0-star property
The Inn At Fox Hollow Hotel
9.2/10 Wonderful! (1,000 reviews)
Dec 10 - Dec 18
8 night stay
Los Angeles (LAX) to New York (JFK)
JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $2,371, price is now $1,478 per person
$1,478
per person
found 1 day ago
Even though we lost power do to the storm the staff was very accommodating in helping with a bad situation.
Reviewed on Sep 29, 2026
5.0-star property
1 Hotel Central Park
Manhattan
9/10 Wonderful! (1,003 reviews)
Dec 19 - Dec 25
6 night stay
Los Angeles (LAX) to New York (JFK)
Alaska Airlines • Coach
New York (JFK) to Los Angeles (LAX)
Southwest Airlines • Coach
Save 100% on your flight
Price was $5,033, price is now $3,139 per person
$3,139
per person
found 18 hours ago
3.5-star property
Citadines Connect Fifth Avenue - Times Square New York
Manhattan
8/10 Very Good! (1,998 reviews)
Dec 3 - Dec 9
6 night stay
Los Angeles (LAX) to New York (JFK)
Delta • Coach
New York (JFK) to Los Angeles (LAX)
Frontier Airlines • Coach
Save 100% on your flight
Price was $2,803, price is now $1,817 per person
$1,817
per person
found 1 day ago
Top rated hotels for your Southold vacation package
The Shoals Suites and Slips
61600 Main Rd Southold NY
1.41 mi from city center
$254 nightly
The price is $286 total per night
$286 total
Oct 1 - Oct 2
Total with taxes and fees
Guests of The Shoals Suites and Slips enjoy features like a business center, free use of bicycles and a computer station. Front-desk staff can assist with concierge services, luggage storage, and securing valuables. Additional amenities include express check-out, a ballroom, and wedding services.
Free WiFi
Restaurant
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Free Cancellation
Reserve now, pay when you stay
15.32 mi from city center
$78 nightly
The price is $90 total per night
$90 total
Oct 6 - Oct 7
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex features free WiFi in public areas and a picnic area. Free parking is included with your stay. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area.
Pet friendly
Parking included
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Free Cancellation
Reserve now, pay when you stay
14.97 mi from city center
$218 nightly
The price is $251 total per night
$251 total
Oct 4 - Oct 5
Total with taxes and fees
Guests of Water's Edge Resort & Spa have access to a private beach, a full-service spa, and an indoor pool. You can put free valet parking to good use if you drive. The 24-hour front desk has staff standing by to help with tours or tickets, securing valuables, and luggage storage. Other amenities at this beach resort include a gym, a sauna, and outdoor tennis courts.
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.
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