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
Price found within the past 48 hours. Click for updated prices.
5-night Southold vacations
Price found within the past 48 hours. Click for updated prices.
6-7 night Southold vacations
Price found within the past 48 hours. Click for updated prices.
Flight deals to Southold
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, Dec 18 - Mon, Jan 6
MIA
Miami
LGA
New York
$63 Roundtrip, found 2 days ago
$63
Roundtrip
found 2 days ago
Thu, Nov 21 - Fri, Nov 22
FLL
Fort Lauderdale
EWR
New York
$77 Roundtrip, found 6 days ago
$77
Roundtrip
found 6 days ago
Wed, Dec 4 - Wed, Dec 4
MCO
Orlando
LGA
New York
$83 Roundtrip, found 1 day ago
$83
Roundtrip
found 1 day ago
Top rated hotels for your Southold vacation
The Shoals Suites and Slips
61600 Main Rd, Southold, NY
1.41 mi from city center
The price is $206 per night
$206
includes taxes & fees
$183 per night
Dec 15 - Dec 16
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.
Breakfast included
Free WiFi
Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
Free Cancellation
Reserve now, pay when you stay
17.88 mi from city center
The price is $88 per night
$88
includes taxes & fees
$77 per night
Dec 15 - Dec 16
A stay at Quality Inn Old Saybrook - Westbrook places you in the heart of Old Saybrook, a 5-minute drive from Essex Steam Train and 5 minutes from Essex Library.
Pool
Breakfast included
Sound View Greenport
58775 County Rd 48, Greenport, NY
2.63 mi from city center
The price is $201 per night
$201
includes taxes & fees
$176 per night
Dec 2 - Dec 3
When you stay at Sound View Greenport in Greenport, you'll be by the ocean, within a 5-minute drive of Kontokosta Winery and 67 Steps Beach.
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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^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.