Cheap Vacations in Southold

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3-night Southold vacations

Price found within the past 48 hours. Click for updated prices.
Windrose On Hudson

Windrose On Hudson

3 out of 5
Save 100% on your flight
Price was $479, price is now $322 per person
$322
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to New York (LGA)
Mountain Springs Lake Resort

Mountain Springs Lake Resort

3.5 out of 5
Price was $579, price is now $331 per person
$331
per person
Feb 25 - Feb 28
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Newark Liberty Intl. Airport (EWR)
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $954, price is now $573 per person
$573
per person
Mar 13 - Mar 16
found 16 hours ago
Roundtrip flight included
Los Angeles (LAX) 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
Price was $1,285, price is now $783 per person
$783
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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
Price was $1,113, price is now $679 per person
$679
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to New York (JFK)
Pendry Natirar

Pendry Natirar

5 out of 5
Save 100% on your flight
Price was $1,776, price is now $1,104 per person
$1,104
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Newark Liberty Intl. Airport (EWR)
CODA Williamsburg

CODA Williamsburg

4 out of 5
Save 100% on your flight
Price was $629, price is now $395 per person
$395
per person
Feb 19 - Feb 22
found 14 hours ago
Roundtrip flight included
Charlotte (CLT) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $1,529, price is now $967 per person
$967
per person
Feb 19 - Feb 22
found 14 hours ago
Roundtrip flight included
Charlotte (CLT) 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
Price was $676, price is now $441 per person
$441
per person
Feb 22 - Feb 25
found 22 hours ago
Roundtrip flight included
Charlotte (CLT) to New York (JFK)
The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Save 100% on your flight
Price was $1,543, price is now $1,036 per person
$1,036
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Paradise Stream Resort

Paradise Stream Resort

3.5 out of 5
Price was $762, price is now $516 per person
$516
per person
Feb 25 - Feb 28
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Newark Liberty Intl. Airport (EWR)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
Price was $1,054, price is now $716 per person
$716
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to New York (JFK)

4-night Southold vacations

Price found within the past 48 hours. Click for updated prices.
voco Fiorello - LaGuardia Airport by IHG

voco Fiorello - LaGuardia Airport by IHG

4 out of 5
Save 100% on your flight
Price was $461, price is now $281 per person
$281
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to New York (JFK)
Hotel Alameda Highline

Hotel Alameda Highline

4.5 out of 5
Price was $2,655, price is now $477 per person
$477
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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
Price was $659, price is now $375 per person
$375
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to New York (JFK)
American Hotel

American Hotel

3.5 out of 5
Save 100% on your flight
Price was $588, price is now $343 per person
$343
per person
Mar 5 - Mar 9
found 9 hours ago
Roundtrip flight included
Charlotte (CLT) to Newark Liberty Intl. Airport (EWR)
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Save 100% on your flight
Price was $819, price is now $483 per person
$483
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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
Price was $947, price is now $563 per person
$563
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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
Price was $832, price is now $501 per person
$501
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to New York (JFK)
The Asbury Hotel

The Asbury Hotel

3.5 out of 5
Save 100% on your flight
Price was $608, price is now $374 per person
$374
per person
Mar 5 - Mar 9
found 9 hours ago
Roundtrip flight included
Charlotte (CLT) to Newark Liberty Intl. Airport (EWR)
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Price was $652, price is now $409 per person
$409
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New York (JFK)
Somerset Hills Hotel, Tapestry Collection by Hilton

Somerset Hills Hotel, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $488, price is now $309 per person
$309
per person
Mar 5 - Mar 9
found 9 hours ago
Roundtrip flight included
Charlotte (CLT) to Newark Liberty Intl. Airport (EWR)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
Price was $603, price is now $390 per person
$390
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to New York (JFK)
New York LaGuardia Airport Marriott

New York LaGuardia Airport Marriott

3.5 out of 5
Save 100% on your flight
Price was $508, price is now $337 per person
$337
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to New York (JFK)

5-night Southold vacations

Price found within the past 48 hours. Click for updated prices.
voco Fiorello - LaGuardia Airport by IHG

voco Fiorello - LaGuardia Airport by IHG

4 out of 5
Save 100% on your flight
Price was $679, price is now $457 per person
$457
per person
Feb 27 - Mar 4
found 1 day 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
Price was $3,516, price is now $2,004 per person
$2,004
per person
Feb 24 - Mar 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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
Price was $902, price is now $548 per person
$548
per person
Feb 24 - Mar 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $996, price is now $605 per person
$605
per person
Feb 27 - Mar 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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
Price was $1,250, price is now $760 per person
$760
per person
Feb 24 - Mar 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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
Price was $1,025, price is now $631 per person
$631
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
The Iroquois New York

The Iroquois New York

4.5 out of 5
Save 100% on your flight
Price was $1,107, price is now $717 per person
$717
per person
Feb 18 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
Price was $1,964, price is now $1,287 per person
$1,287
per person
Mar 10 - Mar 15
found 18 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Windrose On Hudson

Windrose On Hudson

3 out of 5
Save 100% on your flight
Price was $855, price is now $564 per person
$564
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (LGA)
The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Save 100% on your flight
Price was $2,784, price is now $1,872 per person
$1,872
per person
Mar 6 - Mar 11
found 18 hours ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
Park Lane New York

Park Lane New York

5 out of 5
Save 100% on your flight
Price was $1,588, price is now $1,070 per person
$1,070
per person
Mar 10 - Mar 15
found 18 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Fairfield Inn & Suites New York Queens/Fresh Meadows

Fairfield Inn & Suites New York Queens/Fresh Meadows

2.5 out of 5
Save 100% on your flight
Price was $762, price is now $517 per person
$517
per person
Feb 27 - Mar 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)

6-7 night Southold vacations

Price found within the past 48 hours. Click for updated prices.
The Lexington Hotel, Autograph Collection

The Lexington Hotel, Autograph Collection

4 out of 5
Save 100% on your flight
Price was $984, price is now $596 per person
$596
per person
Feb 18 - Feb 24
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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
Price was $1,381, price is now $802 per person
$802
per person
Mar 11 - Mar 18
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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
Price was $2,132, price is now $1,245 per person
$1,245
per person
Mar 11 - Mar 18
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to New York (JFK)
New York Marriott Downtown

New York Marriott Downtown

4 out of 5
Save 100% on your flight
Price was $2,155, price is now $1,262 per person
$1,262
per person
Mar 11 - Mar 18
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to New York (JFK)
Pendry Natirar

Pendry Natirar

5 out of 5
Save 100% on your flight
Price was $3,075, price is now $1,870 per person
$1,870
per person
Feb 18 - Feb 24
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Save 100% on your flight
Price was $1,292, price is now $794 per person
$794
per person
Feb 18 - Feb 24
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Allegria Hotel

Allegria Hotel

4 out of 5
Save 100% on your flight
Price was $1,093, price is now $675 per person
$675
per person
Mar 11 - Mar 18
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
Price was $2,363, price is now $1,516 per person
$1,516
per person
Mar 11 - Mar 18
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to New York (JFK)
Hotel Hendricks

Hotel Hendricks

4 out of 5
Save 100% on your flight
Price was $1,274, price is now $832 per person
$832
per person
Mar 8 - Mar 15
found 9 hours ago
Roundtrip flight included
Orlando (MCO) to New York (JFK)
Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Save 100% on your flight
Price was $2,702, price is now $1,776 per person
$1,776
per person
Mar 11 - Mar 18
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to New York (JFK)
Hotel Belleclaire

Hotel Belleclaire

4 out of 5
Save 100% on your flight
Price was $1,727, price is now $1,134 per person
$1,134
per person
Mar 11 - Mar 18
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to New York (JFK)
Windrose On Hudson

Windrose On Hudson

3 out of 5
Save 100% on your flight
Price was $1,023, price is now $683 per person
$683
per person
Feb 18 - Feb 24
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (LGA)

Flight deals to Southold

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

Wed, Feb 4 - Sat, Feb 7
MCO
Orlando
LGA
New York
$50 Roundtrip, found 5 days ago
$50
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Wed, Feb 4 from Orlando to New York, returning Sat, Feb 7, priced at $50 found 5 days ago
Sat, Feb 14 - Wed, Feb 18
MCO
Orlando
EWR
New York
$54 Roundtrip, found 3 days ago
$54
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Sat, Feb 14 from Orlando to New York, returning Wed, Feb 18, priced at $54 found 3 days ago
Tue, Feb 10 - Wed, Feb 25
MIA
Miami
EWR
New York
$55 Roundtrip, found 3 days ago
$55
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Feb 10 from Miami to New York, returning Wed, Feb 25, priced at $55 found 3 days 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
$162 nightly
The price is $185 total per night
$185 total
Jan 20 - Jan 21
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.
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
2.63 mi from city center
$159 nightly
The price is $182 total per night
$182 total
Jan 21 - Jan 22
Total with taxes and fees
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.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Free Cancellation
Reserve now, pay when you stay
15.32 mi from city center
$79 nightly
The price is $91 total per night
$91 total
Jan 19 - Jan 20
Total with taxes and fees
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.
Pet friendly
Parking included
Don't see what you're looking for?
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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.