Cheap Vacations in Southold
- Southold vacations
- 3-night Southold vacations
- 4-night Southold vacations
- 5-night Southold vacations
- 6-7 night Southold vacations
3-night Southold vacations
Price found within the past 48 hours. Click for updated prices.
4-night Southold vacations
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5-night Southold vacations
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6-7 night Southold vacations
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Flight deals to Southold
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
FLL
Fort Lauderdale
EWR
New York
$86 Roundtrip, found 1 day ago
$86
Roundtrip
found 1 day ago
MCO
Orlando
LGA
New York
$87 Roundtrip, found 2 hours ago
$87
Roundtrip
found 2 hours ago
FLL
Fort Lauderdale
LGA
New York
$90 Roundtrip, just found
$90
Roundtrip
just found
Top rated hotels for your Southold vacation
The Shoals Suites and Slips
61600 Main Rd Southold NY
1.41 mi from city center
$194 nightly
The price is $218 total per night
$218 total
May 3 - May 4
Total with taxes and fees
When you stay at The Shoals Suites and Slips in Southold, you'll be near the bay, within a 5-minute drive of The Old Field Vineyards and Mattebella Vineyards.
Free WiFi
Air conditioning
Vine & Sand
47100 New York 25 Southold NY
1.32 mi from city center
$361 nightly
The price is $412 total per night
$412 total
Apr 20 - Apr 21
Total with taxes and fees
With a stay at Vine & Sand in Southold, you'll be a 2-minute walk from Mattebella Vineyards and 8 minutes by foot from Corey Creek Winery.
Pool
Breakfast included
The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
Free Cancellation
Reserve now, pay when you stay
11.94 mi from city center
$140 nightly
The price is $160 total per night
$160 total
Apr 26 - Apr 27
Total with taxes and fees
When you stay at The Bentley Hotel Southampton in Southampton, you'll be near the airport, within a 5-minute drive of The Hamptons Beaches and Meschutt Beach.
Pool
Pet friendly
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.
Top Picks
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^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.
