
Southold Vacations
Book a Hotel + Flight or Car together to unlock savings
Photo by Benny Goh
- Plan, book, travel with confidence
Better together
Save up to NT$5,067 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Find the Best Southold Vacation Packages
Southold Hotel Deals

The Shoals Suites and Slips
61600 Main Rd, Southold, NY
The price is NT$11,048 per night from Aug 3 to Aug 4
NT$11,048
NT$13,365 total
Aug 3 - Aug 4
includes taxes & fees
9.4/10 Exceptional! (186 reviews)
"Would stay again. So beautiful and clean."
Reviewed on 2025/7/27

Vine & Sand
47100 New York 25, Southold, NY
10/10 Exceptional! (8 reviews)
"Beautiful house and trip to stay in the North Fork. Hosts are incredible. Highly recommend!!"
Reviewed on 2025/7/23

Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is NT$3,284 per night from Aug 10 to Aug 11
NT$3,284
NT$3,776 total
Aug 10 - Aug 11
includes taxes & fees
7.6/10 Good! (1,000 reviews)
"This hotel is modern and provides as close to a full breakfast as you could get under the heading of "continental". The room was spacious and clean. My one complain was the overall design of the building. First, like us, everyone had to drive around both sides of the building to find the office which ..."
Reviewed on 2025/7/27
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.
Discover the most popular places to visit in Southold

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.
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.
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.
Frequently asked questions
Other vacations you might like
Expedia's Latest Trends
Hotels
Flights
Packages
General
- Visit Niagara Falls
- Visit Geneva
- Visit Syracuse
- Visit Amenia
- Visit Napa
- Visit Palm Springs
- Visit Yellowstone National Park
- Visit Southampton
- Visit Saratoga Springs
- Visit Lake George
- Visit Cold Spring Harbor
- Visit White Plains
- Visit Tarrytown
- Visit Grand Island
- Visit Cuba
- Visit San Diego
- Visit Bear Mountain
- Visit Newport Beach
- Visit Honolulu
- Visit Hampton Bays
- Visit Ithaca
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.