Cheap Vacations in Southold

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3-night Southold vacations

Price found within the past 48 hours. Click for updated prices.
Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Price was $661, price is now $439 per person
$439
per person
Apr 16 - Apr 19
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 $1,499, price is now $927 per person
$927
per person
Apr 23 - Apr 26
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
Hotel St. James

Hotel St. James

2.5 out of 5
Price was $794, price is now $499 per person
$499
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 24 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
Price was $1,019, price is now $671 per person
$671
per person
Apr 16 - Apr 19
found 1 day 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 $1,366, 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 Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Price was $1,004, price is now $662 per person
$662
per person
Apr 16 - Apr 19
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 18 hours 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 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
Hyatt Regency Jersey City on the Hudson

Hyatt Regency Jersey City on the Hudson

4 out of 5
Save 100% on your flight
Price was $673, price is now $460 per person
$460
per person
Apr 22 - Apr 25
found 1 day 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 20 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.
Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
Price was $646, price is now $422 per person
$422
per person
Apr 14 - Apr 18
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
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 9 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)
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 21 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 New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Save 100% on your flight
Price was $1,212, price is now $769 per person
$769
per person
Apr 18 - Apr 22
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 $1,235, price is now $784 per person
$784
per person
Apr 18 - Apr 22
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)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
Price was $1,484, price is now $952 per person
$952
per person
Apr 18 - Apr 22
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 $771, price is now $502 per person
$502
per person
Apr 18 - Apr 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
The Maidstone

The Maidstone

4 out of 5
Save 100% on your flight
Price was $1,435, price is now $936 per person
$936
per person
Apr 14 - Apr 18
found 9 hours ago
Roundtrip flight included
Dallas (DFW) 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 $1,098, price is now $727 per person
$727
per person
Apr 22 - Apr 26
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.
Hotel 1080 Brooklyn

Hotel 1080 Brooklyn

3.5 out of 5
Save 100% on your flight
Price was $704, price is now $471 per person
$471
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,240, 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 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
Nova Hotel Brooklyn

Nova Hotel Brooklyn

3 out of 5
Save 100% on your flight
Price was $774, price is now $480 per person
$480
per person
Apr 23 - 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
Save 100% on your flight
Price was $4,057, price is now $2,524 per person
$2,524
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
Price was $1,968, price is now $1,235 per person
$1,235
per person
Apr 22 - Apr 27
found 19 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 1 hour ago
Roundtrip flight included
Burbank (BUR) to Newark Liberty Intl. Airport (EWR)
The William Vale

The William Vale

5 out of 5
Save 100% on your flight
Price was $1,916, price is now $1,262 per person
$1,262
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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)
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)
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 5 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 3 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 5 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 9 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 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Save 100% on your flight
Price was $1,351, price is now $962 per person
$962
per person
Apr 9 - Apr 15
found 3 hours ago
Roundtrip flight included
Los Angeles (LAX) 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.

Wed, Apr 22 - Sat, Apr 25
ATL
Atlanta
LGA
New York
$56 Roundtrip, found 1 day ago
$56
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Atlanta to New York, returning Sat, Apr 25, priced at $56 found 1 day ago
Mon, Mar 23 - Tue, Mar 24
ATL
Atlanta
JFK
New York
$56 Roundtrip, found 21 hours ago
$56
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Mon, Mar 23 from Atlanta to New York, returning Tue, Mar 24, priced at $56 found 21 hours 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, just found
$56
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, May 8 from Atlanta to New York, returning Sat, May 9, priced at $56 just found
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
Wed, Apr 1 - Sat, Apr 11
MCO
Orlando
JFK
New York
$80 Roundtrip, found 6 days ago
$80
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Apr 1 from Orlando to New York, returning Sat, Apr 11, priced at $80 found 6 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 4 - Mar 5
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.
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 8 - Mar 9
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 4 - Mar 5
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.