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
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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.
Mon, Mar 10 - Mon, Mar 17
MCO
Orlando
HVN
New Haven
$82 Roundtrip, found 1 day ago
$82
Roundtrip
found 1 day ago
Wed, Dec 11 - Tue, Dec 17
MIA
Miami
EWR
New York
$83 Roundtrip, found 4 days ago
$83
Roundtrip
found 4 days ago
Thu, Dec 5 - Sun, Dec 8
MCO
Orlando
SWF
Newburgh
$84 Roundtrip, found 5 days ago
$84
Roundtrip
found 5 days 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 $215 per night
$215
includes taxes & fees
$191 per night
Dec 9 - Dec 10
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.
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 10 - Dec 11
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.
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
The price is $76 per night
$76
includes taxes & fees
$66 per night
Dec 1 - Dec 2
Located in Old Saybrook (Saybrook Manor), Pier Blue Inn Old Saybrook - Essex is within a 5-minute drive of Chalker Beach and Saybrook Country Barn.
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.