Cheap Vacations in Southold

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3-night Southold vacations

Price found within the past 48 hours. Click for updated prices.
Hotel 57

Hotel 57

4 out of 5
Save 100% on your flight
Price was $671, price is now $462 per person
$462
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Save 100% on your flight
Price was $1,360, price is now $810 per person
$810
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Save 100% on your flight
Price was $1,506, price is now $932 per person
$932
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $2,304, price is now $1,507 per person
$1,507
per person
Apr 9 - Apr 12
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
Save 100% on your flight
Price was $1,366, price is now $899 per person
$899
per person
Apr 6 - Apr 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
Price was $770, price is now $509 per person
$509
per person
Apr 6 - Apr 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,072, price is now $715 per person
$715
per person
Apr 6 - Apr 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
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 $1,071, price is now $715 per person
$715
per person
Apr 6 - Apr 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
The George

The George

4 out of 5
Save 100% on your flight
Price was $845, price is now $565 per person
$565
per person
Apr 7 - Apr 10
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Save 100% on your flight
Price was $818, price is now $548 per person
$548
per person
Apr 6 - Apr 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
Hyatt Union Square New York

Hyatt Union Square New York

4 out of 5
Save 100% on your flight
Price was $1,014, price is now $689 per person
$689
per person
Apr 24 - Apr 27
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
Placemakr Wall Street

Placemakr Wall Street

4 out of 5
Save 100% on your flight
Price was $924, price is now $633 per person
$633
per person
Apr 23 - Apr 26
found 23 hours 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.
Nova Hotel Brooklyn

Nova Hotel Brooklyn

3 out of 5
Price was $646, price is now $405 per person
$405
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Hotel St. James

Hotel St. James

2.5 out of 5
Price was $972, price is now $498 per person
$498
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
Topping Rose House

Topping Rose House

4.5 out of 5
Price was $1,672, price is now $916 per person
$916
per person
Apr 14 - Apr 18
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Save 100% on your flight
Price was $2,083, price is now $1,219 per person
$1,219
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
Court Square Hotel Long Island City New York , Belvilla District 6 Formerly Sonder

Court Square Hotel Long Island City New York , Belvilla District 6 Formerly Sonder

3.5 out of 5
Price was $831, price is now $515 per person
$515
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $2,620, price is now $1,639 per person
$1,639
per person
Apr 16 - Apr 20
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Hyatt Union Square New York

Hyatt Union Square New York

4 out of 5
Save 100% on your flight
Price was $1,478, price is now $927 per person
$927
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Price was $1,199, price is now $753 per person
$753
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $755, price is now $478 per person
$478
per person
Apr 18 - Apr 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
Holiday Inn Express New York - Manhattan West Side by IHG

Holiday Inn Express New York - Manhattan West Side by IHG

2.5 out of 5
Price was $934, price is now $591 per person
$591
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Save 100% on your flight
Price was $1,003, price is now $637 per person
$637
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Price was $928, price is now $591 per person
$591
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

5-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 $775, price is now $549 per person
$549
per person
Apr 22 - Apr 27
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) 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 $1,240, price is now $696 per person
$696
per person
Apr 6 - Apr 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Save 100% on your flight
Price was $2,066, price is now $1,280 per person
$1,280
per person
Apr 3 - Apr 8
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) 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 $1,968, price is now $1,235 per person
$1,235
per person
Apr 22 - Apr 27
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
Price was $1,271, price is now $810 per person
$810
per person
Apr 6 - Apr 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
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 $1,775, price is now $1,137 per person
$1,137
per person
Apr 6 - Apr 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,817, price is now $1,184 per person
$1,184
per person
Apr 22 - Apr 27
found 4 hours ago
Roundtrip flight included
Burbank (BUR) to Newark Liberty Intl. Airport (EWR)
The Maidstone

The Maidstone

4 out of 5
Save 100% on your flight
Price was $2,594, price is now $1,734 per person
$1,734
per person
Apr 18 - Apr 23
found 2 hours ago
Roundtrip flight included
Orange County (SNA) to New York (JFK)
Holiday Inn Express New York - Manhattan West Side by IHG

Holiday Inn Express New York - Manhattan West Side by IHG

2.5 out of 5
Save 100% on your flight
Price was $1,308, price is now $894 per person
$894
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
Price was $1,154, price is now $795 per person
$795
per person
Apr 18 - Apr 23
found 2 hours ago
Roundtrip flight included
Orange County (SNA) to New York (JFK)
Harpoon House

Harpoon House

3 out of 5
Save 100% on your flight
Price was $1,232, price is now $857 per person
$857
per person
Apr 18 - Apr 23
found 2 hours ago
Roundtrip flight included
Orange County (SNA) to New York (JFK)
Hilton Garden Inn Long Island City New York

Hilton Garden Inn Long Island City New York

3 out of 5
Save 100% on your flight
Price was $1,037, price is now $729 per person
$729
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)

6-7 night Southold vacations

Price found within the past 48 hours. Click for updated prices.
Paramount Times Square – A Generator Hotel

Paramount Times Square – A Generator Hotel

4 out of 5
Save 100% on your flight
Price was $1,136, price is now $806 per person
$806
per person
Apr 3 - Apr 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
The William Hotel Midtown, New York

The William Hotel Midtown, New York

2 out of 5
Save 100% on your flight
Price was $2,096, price is now $1,218 per person
$1,218
per person
Apr 21 - Apr 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
Price was $1,485, price is now $875 per person
$875
per person
Apr 19 - Apr 25
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Price was $2,226, price is now $1,366 per person
$1,366
per person
Apr 12 - Apr 19
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Save 100% on your flight
Price was $2,705, price is now $1,673 per person
$1,673
per person
Apr 3 - Apr 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $2,092, price is now $1,299 per person
$1,299
per person
Apr 19 - Apr 25
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) 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 $2,735, price is now $1,804 per person
$1,804
per person
Apr 3 - Apr 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
Save 100% on your flight
Price was $1,558, price is now $1,054 per person
$1,054
per person
Apr 18 - Apr 24
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
Hyatt Regency Times Square

Hyatt Regency Times Square

3.5 out of 5
Save 100% on your flight
Price was $1,611, price is now $1,124 per person
$1,124
per person
Apr 3 - Apr 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $2,420, price is now $1,705 per person
$1,705
per person
Apr 4 - Apr 10
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Ace Hotel New York

Ace Hotel New York

4 out of 5
Price was $1,436, price is now $1,020 per person
$1,020
per person
Apr 12 - Apr 19
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

Flight deals to Southold

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

Fri, May 15 - Sat, May 16
ATL
Atlanta
LGA
New York
$56 Roundtrip, found 2 hours ago
$56
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Fri, May 15 from Atlanta to New York, returning Sat, May 16, priced at $56 found 2 hours ago
Mon, Mar 23 - Tue, Mar 24
ATL
Atlanta
JFK
New York
$56 Roundtrip, found 1 day ago
$56
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Mar 23 from Atlanta to New York, returning Tue, Mar 24, priced at $56 found 1 day ago
Wed, Apr 22 - Wed, Apr 22
MCO
Orlando
LGA
New York
$56 Roundtrip, found 5 days ago
$56
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Orlando to New York, returning Wed, Apr 22, priced at $56 found 5 days ago
Fri, May 8 - Sat, May 9
ATL
Atlanta
EWR
New York
$56 Roundtrip, found 3 hours ago
$56
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Fri, May 8 from Atlanta to New York, returning Sat, May 9, priced at $56 found 3 hours ago
Thu, Mar 12 - Tue, Mar 17
MIA
Miami
LGA
New York
$80 Roundtrip, found 6 days ago
$80
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Thu, Mar 12 from Miami to New York, returning Tue, Mar 17, priced at $80 found 6 days ago
Sat, Jun 6 - Tue, Jun 9
MCO
Orlando
EWR
New York
$82 Roundtrip, found 3 days ago
$82
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Jun 6 from Orlando to New York, returning Tue, Jun 9, priced at $82 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
$169 nightly
The price is $193 total per night
$193 total
Mar 8 - Mar 9
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
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
15.32 mi from city center
$104 nightly
The price is $120 total per night
$120 total
Mar 5 - Mar 6
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 Crystal Lake Town Park.
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
2.63 mi from city center
$175 nightly
The price is $200 total per night
$200 total
Mar 5 - Mar 6
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.
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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.