Cheap Vacations in Southold

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Southold vacations

Price found within the past 48 hours. Click for updated prices.
Somerset Hills Hotel, Tapestry Collection by Hilton

Somerset Hills Hotel, Tapestry Collection by Hilton

4 out of 5
per person
Feb 13 - Feb 16
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
The William Vale

The William Vale

5 out of 5
Save 100% on your flight
per person
Feb 7 - Feb 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to New York (JFK)
Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Save 100% on your flight
per person
Feb 13 - Feb 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
Feb 7 - Feb 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Feb 13 - Feb 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
BeHome by LuxUrban

BeHome by LuxUrban

2 out of 5
Manhattan
Save 100% on your flight
per person
Feb 13 - Feb 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Feb 7 - Feb 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to New York (JFK)
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)

3-night Southold vacations

Price found within the past 48 hours. Click for updated prices.
Somerset Hills Hotel, Tapestry Collection by Hilton

Somerset Hills Hotel, Tapestry Collection by Hilton

4 out of 5
per person
Feb 13 - Feb 16
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Save 100% on your flight
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to New York (JFK)
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Save 100% on your flight
per person
Feb 28 - Mar 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Mandarin Oriental, New York

Mandarin Oriental, New York

5 out of 5
Save 100% on your flight
per person
Feb 26 - Mar 1
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to New York (JFK)
The Carlyle, A Rosewood Hotel

The Carlyle, A Rosewood Hotel

5 out of 5
Save 100% on your flight
per person
Feb 13 - Feb 16
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Save 100% on your flight
per person
Feb 28 - Mar 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Save 100% on your flight
per person
Feb 14 - Feb 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Save 100% on your flight
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Sheraton Parsippany Hotel

Sheraton Parsippany Hotel

4 out of 5
per person
Feb 13 - Feb 16
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Hilton Parsippany

Hilton Parsippany

4 out of 5
per person
Feb 13 - Feb 16
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)

4-night Southold vacations

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
per person
Feb 17 - Feb 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The William Vale

The William Vale

5 out of 5
Save 100% on your flight
per person
Feb 7 - Feb 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Save 100% on your flight
per person
Feb 17 - Feb 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Save 100% on your flight
per person
Feb 13 - Feb 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
Feb 7 - Feb 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Save 100% on your flight
per person
Feb 13 - Feb 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Blakely by LuxUrban

The Blakely by LuxUrban

2.5 out of 5
Save 100% on your flight
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
per person
Feb 7 - Feb 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Tuscany by LuxUrban

Tuscany by LuxUrban

3 out of 5
Save 100% on your flight
per person
Feb 17 - Feb 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Herald by LuxUrban

The Herald by LuxUrban

2.5 out of 5
Save 100% on your flight
per person
Feb 17 - Feb 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Washington by LuxUrban

The Washington by LuxUrban

3 out of 5
Save 100% on your flight
per person
Feb 17 - Feb 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Save 100% on your flight
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)

5-night Southold vacations

Price found within the past 48 hours. Click for updated prices.
Hotel 32 32

Hotel 32 32

4 out of 5
Save 100% on your flight
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Save 100% on your flight
per person
Feb 3 - Feb 8
found 23 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Save 100% on your flight
per person
Feb 3 - Feb 8
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
New York Marriott Downtown

New York Marriott Downtown

4 out of 5
Save 100% on your flight
per person
Feb 3 - Feb 8
found 23 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Save 100% on your flight
per person
Feb 3 - Feb 8
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
per person
Feb 10 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to New York (JFK)
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
per person
Feb 10 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to New York (JFK)
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
per person
Feb 8 - Feb 13
found 5 hours ago
Roundtrip flight included
Miami (MIA) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
per person
Feb 3 - Feb 8
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Newark Liberty International Airport Marriott

Newark Liberty International Airport Marriott

4 out of 5
Save 100% on your flight
per person
Feb 12 - Feb 17
found 18 hours ago
Roundtrip flight included
San Juan (SJU) to Newark Liberty Intl. Airport (EWR)
The Prince Kitano New York

The Prince Kitano New York

4.5 out of 5
Save 100% on your flight
per person
Feb 8 - Feb 13
found 5 hours ago
Roundtrip flight included
Miami (MIA) to New York (JFK)
The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Save 100% on your flight
per person
Feb 8 - Feb 13
found 5 hours ago
Roundtrip flight included
Miami (MIA) to New York (JFK)

6-7 night Southold vacations

Price found within the past 48 hours. Click for updated prices.
Hotel 32 32

Hotel 32 32

4 out of 5
Save 100% on your flight
per person
Feb 2 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
The William Vale

The William Vale

5 out of 5
per person
Feb 13 - Feb 20
found 14 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
per person
Feb 2 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to New York (JFK)
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Save 100% on your flight
per person
Feb 13 - Feb 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
Feb 13 - Feb 20
found 14 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Tuscany by LuxUrban

Tuscany by LuxUrban

3 out of 5
Save 100% on your flight
per person
Feb 13 - Feb 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hotel 57 by LuxUrban

Hotel 57 by LuxUrban

4 out of 5
Save 100% on your flight
per person
Feb 13 - Feb 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Save 100% on your flight
per person
Feb 13 - Feb 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Washington by LuxUrban

The Washington by LuxUrban

3 out of 5
Save 100% on your flight
per person
Feb 13 - Feb 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
per person
Feb 15 - Feb 21
found 12 hours ago
Roundtrip flight included
Miami (MIA) to New York (JFK)
The Blakely by LuxUrban

The Blakely by LuxUrban

2.5 out of 5
Save 100% on your flight
per person
Feb 13 - Feb 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Save 100% on your flight
per person
Feb 13 - Feb 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)

Flight deals to Southold

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, Jan 14 - Tue, Jan 21
MCO
Orlando
LGA
New York
$58 Roundtrip, found 2 days ago
$58
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Jan 14 from Orlando to New York, returning Tue, Jan 21, priced at $58 found 2 days ago
Fri, Apr 25 - Wed, Apr 30
MIA
Miami
LGA
New York
$62 Roundtrip, found 6 days ago
$62
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, Apr 25 from Miami to New York, returning Wed, Apr 30, priced at $62 found 6 days ago
Wed, Feb 26 - Wed, Feb 26
MCO
Orlando
JFK
New York
$67 Roundtrip, found 3 hours ago
$67
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Wed, Feb 26 from Orlando to New York, returning Wed, Feb 26, priced at $67 found 3 hours ago

Top rated hotels for your Southold vacation

The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd, Southold, NY
1.41 mi from city center
The price is $215 per night
$215
includes taxes & fees
$188 per night
Jan 5 - Jan 6
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.
Residence Inn by Marriott New York Long Island East End

Residence Inn by Marriott New York Long Island East End

3 out of 5
2012 Old Country Road, Riverhead, NY
Free Cancellation
Reserve now, pay when you stay
17.97 mi from city center
The price is $135 per night
$135
includes taxes & fees
$118 per night
Jan 20 - Jan 21
With a stay at Residence Inn by Marriott New York Long Island East End in Riverhead, you'll be within a 15-minute walk of Tanger Outlet Center and Riverhead Raceway.
Hyatt Place Long Island East End

Hyatt Place Long Island East End

3 out of 5
451 East Main Street, Riverhead, NY
Free Cancellation
Reserve now, pay when you stay
15.66 mi from city center
The price is $118 per night
$118
includes taxes & fees
$103 per night
Jan 12 - Jan 13
With a stay at Hyatt Place Long Island East End in Riverhead, you'll be on a river, just a 5-minute walk from Suffolk Theater and 6 minutes by foot from All Star Bowling.
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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.

^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.