Cheap Vacations in Southold

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3-night Southold vacations

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

Night Hotel Broadway

3 out of 5
Save 100% on your flight
Price was $598, price is now $411 per person
$411
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Hotel St. James

Hotel St. James

3 out of 5
Save 100% on your flight
Price was $763, price is now $468 per person
$468
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,237, price is now $775 per person
$775
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,072, price is now $672 per person
$672
per person
Aug 28 - Aug 31
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 $2,047, price is now $1,287 per person
$1,287
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
OYO Times Square

OYO Times Square

4 out of 5
Save 100% on your flight
Price was $845, price is now $538 per person
$538
per person
Sep 8 - Sep 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
San Carlos Hotel

San Carlos Hotel

4.5 out of 5
Save 100% on your flight
Price was $994, price is now $657 per person
$657
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Pendry Natirar

Pendry Natirar

5 out of 5
Save 100% on your flight
Price was $2,725, price is now $1,835 per person
$1,835
per person
Sep 10 - Sep 13
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
Price was $1,182, price is now $796 per person
$796
per person
Sep 11 - Sep 14
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Save 100% on your flight
Price was $759, price is now $520 per person
$520
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Mandarin Oriental, New York

Mandarin Oriental, New York

5 out of 5
Save 100% on your flight
Price was $2,138, price is now $1,466 per person
$1,466
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Allegria Hotel

Allegria Hotel

4 out of 5
Save 100% on your flight
Price was $1,241, price is now $855 per person
$855
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)

4-night Southold vacations

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

Radio Hotel

4 out of 5
Save 100% on your flight
Price was $883, price is now $544 per person
$544
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Wall Street Hotel

The Wall Street Hotel

5 out of 5
Save 100% on your flight
Price was $2,281, price is now $1,326 per person
$1,326
per person
Sep 3 - Sep 7
found 18 hours 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 $4,188, price is now $2,473 per person
$2,473
per person
Sep 3 - Sep 7
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) 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 $1,511, price is now $917 per person
$917
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,654, price is now $1,012 per person
$1,012
per person
Sep 4 - Sep 8
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 $1,984, price is now $1,216 per person
$1,216
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Save 100% on your flight
Price was $3,090, price is now $1,945 per person
$1,945
per person
Sep 3 - Sep 7
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Park Lane New York

Park Lane New York

5 out of 5
Save 100% on your flight
Price was $1,756, price is now $1,117 per person
$1,117
per person
Sep 3 - Sep 7
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $1,631, price is now $1,059 per person
$1,059
per person
Sep 3 - Sep 7
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Plaza, A Fairmont Hotel

The Plaza, A Fairmont Hotel

5 out of 5
Save 100% on your flight
Price was $4,048, price is now $2,635 per person
$2,635
per person
Sep 3 - Sep 7
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
OYO Times Square

OYO Times Square

4 out of 5
Save 100% on your flight
Price was $1,109, price is now $724 per person
$724
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Manner, The Unbound Collection by Hyatt

The Manner, The Unbound Collection by Hyatt

5 out of 5
Save 100% on your flight
Price was $2,413, price is now $1,616 per person
$1,616
per person
Sep 3 - Sep 7
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)

5-night Southold vacations

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

Radio Hotel

4 out of 5
Save 100% on your flight
Price was $793, price is now $479 per person
$479
per person
Aug 23 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Hotel St. James

Hotel St. James

3 out of 5
Save 100% on your flight
Price was $1,106, price is now $643 per person
$643
per person
Aug 19 - Aug 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
Price was $1,912, price is now $1,188 per person
$1,188
per person
Sep 6 - Sep 11
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) 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 $1,985, price is now $1,285 per person
$1,285
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,840, price is now $1,200 per person
$1,200
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $2,465, price is now $1,649 per person
$1,649
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Houston (IAH) to New York (JFK)
Hotel 32 32

Hotel 32 32

4 out of 5
Save 100% on your flight
Price was $1,422, price is now $978 per person
$978
per person
Sep 10 - Sep 15
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Marco LaGuardia Hotel

Marco LaGuardia Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,889, price is now $1,314 per person
$1,314
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Save 100% on your flight
Price was $956, price is now $666 per person
$666
per person
Aug 23 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Aura Hotel Times Square

Aura Hotel Times Square

4 out of 5
Price was $1,453, price is now $1,015 per person
$1,015
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Citadines Connect Fifth Avenue New York

Citadines Connect Fifth Avenue New York

3.5 out of 5
Save 100% on your flight
Price was $1,206, price is now $845 per person
$845
per person
Aug 31 - Sep 5
found 1 day ago
Roundtrip flight included
Houston (IAH) to New York (JFK)
The Chemists’ Club Hotel

The Chemists’ Club Hotel

4 out of 5
Save 100% on your flight
Price was $2,229, price is now $1,565 per person
$1,565
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Houston (IAH) to New York (JFK)

6-7 night Southold vacations

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

Radio Hotel

4 out of 5
Save 100% on your flight
Price was $1,177, price is now $723 per person
$723
per person
Aug 25 - Aug 31
found 10 hours ago
Roundtrip flight included
Houston (IAH) to New York (JFK)
Hotel St. James

Hotel St. James

3 out of 5
Save 100% on your flight
Price was $1,467, price is now $803 per person
$803
per person
Aug 23 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Save 100% on your flight
Price was $2,018, price is now $1,190 per person
$1,190
per person
Aug 30 - Sep 6
found 20 hours ago
Roundtrip flight included
Houston (HOU) to New York (JFK)
Park Lane New York

Park Lane New York

5 out of 5
Save 100% on your flight
Price was $2,789, price is now $1,656 per person
$1,656
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $2,526, price is now $1,532 per person
$1,532
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $2,292, price is now $1,397 per person
$1,397
per person
Aug 30 - Sep 6
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 $5,905, price is now $3,656 per person
$3,656
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Ridge Hotel

The Ridge Hotel

3 out of 5
Save 100% on your flight
Price was $1,183, price is now $763 per person
$763
per person
Aug 23 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Save 100% on your flight
Price was $4,639, price is now $3,006 per person
$3,006
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $2,783, price is now $1,804 per person
$1,804
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
WestHouse New York

WestHouse New York

5 out of 5
Save 100% on your flight
Price was $1,525, price is now $995 per person
$995
per person
Aug 23 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Park Central Hotel New York

Park Central Hotel New York

4 out of 5
Save 100% on your flight
Price was $1,372, price is now $898 per person
$898
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to New York (JFK)

Flight deals to Southold

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

Sat, Oct 17 - Wed, Oct 21
MCO
Orlando
LGA
New York
$86 Roundtrip, found 3 days ago
$86
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Oct 17 from Orlando to New York, returning Wed, Oct 21, priced at $86 found 3 days ago
Sat, Nov 14 - Tue, Nov 17
MCO
Orlando
EWR
New York
$86 Roundtrip, found 2 days ago
$86
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Nov 14 from Orlando to New York, returning Tue, Nov 17, priced at $86 found 2 days ago
Thu, Aug 6 - Thu, Aug 13
FLL
Fort Lauderdale
SWF
Newburgh
$104 Roundtrip, found 3 days ago
$104
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Thu, Aug 6 from Fort Lauderdale to Newburgh, returning Thu, Aug 13, priced at $104 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
$397 nightly
The price is $450 total per night
$450 total
Aug 2 - Aug 3
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
$92 nightly
The price is $105 total per night
$105 total
Jul 19 - Jul 20
Total with taxes and fees
With a stay at Pier Blue Inn Old Saybrook - Essex in Old Saybrook (Saybrook Manor), you'll be within a 15-minute drive of Hammonasset Beach State Park and Chalker Beach.
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
2.63 mi from city center
$414 nightly
The price is $473 total per night
$473 total
Aug 12 - Aug 13
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.

Top Picks

^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.