Cheap Vacations in Southold

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4-night Southold vacations

Price found within the past 48 hours. Click for updated prices.
The Hewitt Wellington Hotel

The Hewitt Wellington Hotel

3 out of 5
Price was $464, price is now $339 per person
$339
per person
Feb 20 - Feb 24
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Newark Liberty Intl. Airport (EWR)
Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Save 100% on your flight
Price was $1,663, price is now $981 per person
$981
per person
Mar 7 - Mar 11
found 5 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
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 3 hours ago
Roundtrip flight included
Orlando (MCO) to New York (JFK)
American Hotel

American Hotel

3.5 out of 5
Save 100% on your flight
Price was $600, price is now $379 per person
$379
per person
Feb 20 - Feb 24
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Newark Liberty Intl. Airport (EWR)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Price was $1,424, price is now $970 per person
$970
per person
Mar 14 - Mar 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $566, price is now $389 per person
$389
per person
Feb 20 - Feb 24
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Newark Liberty Intl. Airport (EWR)
Windrose On Hudson

Windrose On Hudson

3 out of 5
Save 100% on your flight
Price was $752, price is now $519 per person
$519
per person
Mar 12 - Mar 16
found 8 hours ago
Roundtrip flight included
San Juan (SJU) to New York (LGA)
The Iroquois New York

The Iroquois New York

4.5 out of 5
Save 100% on your flight
Price was $1,343, price is now $934 per person
$934
per person
Mar 7 - Mar 11
found 5 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
The George

The George

4 out of 5
Save 100% on your flight
Price was $1,009, price is now $706 per person
$706
per person
Feb 20 - Feb 24
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Newark Liberty Intl. Airport (EWR)
Park Lane New York

Park Lane New York

5 out of 5
Save 100% on your flight
Price was $1,201, price is now $862 per person
$862
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Asbury Ocean Club Hotel

Asbury Ocean Club Hotel

4 out of 5
Save 100% on your flight
Price was $959, price is now $695 per person
$695
per person
Feb 20 - Feb 24
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Newark Liberty Intl. Airport (EWR)
Pendry Natirar

Pendry Natirar

5 out of 5
Save 100% on your flight
Price was $2,512, price is now $1,831 per person
$1,831
per person
Feb 27 - Mar 3
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)

5-night Southold vacations

Price found within the past 48 hours. Click for updated prices.
Best Western Plus Meadowlands

Best Western Plus Meadowlands

3.5 out of 5
Save 100% on your flight
Price was $552, price is now $372 per person
$372
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Save 100% on your flight
Price was $895, price is now $452 per person
$452
per person
Feb 25 - Mar 2
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 $1,164, price is now $647 per person
$647
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
Price was $828, price is now $477 per person
$477
per person
Feb 25 - Mar 2
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 $856, price is now $511 per person
$511
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
The Lexington Hotel, Autograph Collection

The Lexington Hotel, Autograph Collection

4 out of 5
Save 100% on your flight
Price was $821, price is now $500 per person
$500
per person
Feb 25 - Mar 2
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 $1,123, price is now $702 per person
$702
per person
Feb 25 - Mar 2
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 $1,009, price is now $631 per person
$631
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Save 100% on your flight
Price was $1,034, price is now $651 per person
$651
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Price was $1,613, price is now $1,032 per person
$1,032
per person
Mar 13 - Mar 18
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New York (JFK)
Arthouse Hotel New York City

Arthouse Hotel New York City

4 out of 5
Save 100% on your flight
Price was $741, price is now $490 per person
$490
per person
Feb 25 - Mar 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Hilton Garden Inn Westchester Dobbs Ferry, NY

Hilton Garden Inn Westchester Dobbs Ferry, NY

3 out of 5
Save 100% on your flight
Price was $594, price is now $402 per person
$402
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)

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 3 days ago
$50
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Feb 4 from Orlando to New York, returning Sat, Feb 7, priced at $50 found 3 days ago
Sat, Feb 14 - Wed, Feb 18
MCO
Orlando
EWR
New York
$54 Roundtrip, found 2 days ago
$54
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, Feb 14 from Orlando to New York, returning Wed, Feb 18, priced at $54 found 2 days ago
Tue, Feb 10 - Wed, Feb 25
MIA
Miami
EWR
New York
$55 Roundtrip, found 1 day ago
$55
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Feb 10 from Miami to New York, returning Wed, Feb 25, priced at $55 found 1 day 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 18 - Jan 19
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
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Free Cancellation
Reserve now, pay when you stay
14.97 mi from city center
$244 nightly
The price is $281 total per night
$281 total
Jan 19 - Jan 20
Total with taxes and fees
With a stay at Water's Edge Resort & Spa in Westbrook (Westbrook Center), you'll be a 4-minute drive from Tanger Outlets and 8 minutes from Clinton Crossing Premium Outlets.
On private beach
Pool
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 18 - Jan 19
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
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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.