Cheap Vacations in Southold

Choose two or more items and save on your trip:

Southold vacations

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

Night Hotel Broadway

3 out of 5
Manhattan
Save 100% on your flight
Price was $726, price is now $497 per person
$497
per person
Nov 19 - Nov 22
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
Manhattan
Save 100% on your flight
Price was $3,012, price is now $1,713 per person
$1,713
per person
Dec 6 - Dec 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,937, price is now $1,134 per person
$1,134
per person
Dec 4 - Dec 7
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
Manhattan
Save 100% on your flight
Price was $2,470, price is now $1,658 per person
$1,658
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Park Lane New York

Park Lane New York

5 out of 5
Manhattan
Save 100% on your flight
Price was $2,283, price is now $1,538 per person
$1,538
per person
Dec 6 - Dec 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
33 Hotel, New York City, Seaport

33 Hotel, New York City, Seaport

5 out of 5
Manhattan
Save 100% on your flight
Price was $2,075, price is now $1,421 per person
$1,421
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Save 100% on your flight
Price was $735, price is now $504 per person
$504
per person
Nov 19 - Nov 22
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
Manhattan
Save 100% on your flight
Price was $1,252, price is now $861 per person
$861
per person
Nov 20 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The William Hotel Midtown, New York

The William Hotel Midtown, New York

3.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,630, price is now $1,127 per person
$1,127
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)

3-night Southold vacations

Price found within the past 48 hours. Click for updated prices.
Log Comfort 3

Log Comfort 3

3 out of 5
Price was $579, price is now $392 per person
$392
per person
Dec 3 - Dec 6
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 $3,012, price is now $1,713 per person
$1,713
per person
Dec 6 - Dec 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,937, price is now $1,134 per person
$1,134
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
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 $3,206, price is now $1,917 per person
$1,917
per person
Dec 13 - Dec 16
found 9 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 $2,235, price is now $1,473 per person
$1,473
per person
Dec 6 - Dec 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
33 Hotel, New York City, Seaport

33 Hotel, New York City, Seaport

5 out of 5
Save 100% on your flight
Price was $1,266, price is now $839 per person
$839
per person
Dec 12 - Dec 15
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 $1,916, price is now $1,282 per person
$1,282
per person
Dec 6 - Dec 9
found 1 day 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 $2,283, price is now $1,538 per person
$1,538
per person
Dec 6 - Dec 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Save 100% on your flight
Price was $2,774, price is now $1,874 per person
$1,874
per person
Dec 13 - Dec 16
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Save 100% on your flight
Price was $726, price is now $497 per person
$497
per person
Nov 19 - Nov 22
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 $735, price is now $504 per person
$504
per person
Nov 19 - Nov 22
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.
Dolce by Wyndham Parsippany

Dolce by Wyndham Parsippany

4 out of 5
Price was $552, price is now $388 per person
$388
per person
Dec 2 - Dec 6
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 $4,185, price is now $2,313 per person
$2,313
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $2,087, price is now $1,217 per person
$1,217
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Save 100% on your flight
Price was $1,508, price is now $923 per person
$923
per person
Dec 10 - Dec 14
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 $1,283, price is now $799 per person
$799
per person
Nov 23 - Nov 27
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 $4,658, price is now $2,990 per person
$2,990
per person
Dec 7 - Dec 11
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 $5,020, price is now $3,290 per person
$3,290
per person
Dec 3 - Dec 7
found 9 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
Park Lane New York

Park Lane New York

5 out of 5
Save 100% on your flight
Price was $3,026, price is now $1,988 per person
$1,988
per person
Dec 7 - Dec 11
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 $2,638, price is now $1,765 per person
$1,765
per person
Dec 10 - Dec 14
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 $2,470, price is now $1,658 per person
$1,658
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
33 Hotel, New York City, Seaport

33 Hotel, New York City, Seaport

5 out of 5
Save 100% on your flight
Price was $2,075, price is now $1,421 per person
$1,421
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Eurostars The Chemists’ Club Hotel

Eurostars The Chemists’ Club Hotel

4 out of 5
Save 100% on your flight
Price was $2,301, price is now $1,610 per person
$1,610
per person
Dec 2 - Dec 6
found 1 day 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.
Log Comfort 3

Log Comfort 3

3 out of 5
Price was $1,025, price is now $683 per person
$683
per person
Dec 6 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Royalton New York

Royalton New York

4 out of 5
Save 100% on your flight
Price was $2,565, price is now $1,596 per person
$1,596
per person
Dec 8 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Citadines Connect Fifth Avenue - Times Square New York

Citadines Connect Fifth Avenue - Times Square New York

3.5 out of 5
Save 100% on your flight
Price was $2,323, price is now $1,447 per person
$1,447
per person
Dec 8 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Save 100% on your flight
Price was $1,849, price is now $1,194 per person
$1,194
per person
Dec 6 - Dec 11
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 $2,047, price is now $1,325 per person
$1,325
per person
Dec 9 - Dec 14
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 $3,661, price is now $2,386 per person
$2,386
per person
Nov 21 - Nov 26
found 8 hours 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 $2,077, price is now $1,359 per person
$1,359
per person
Nov 25 - Nov 30
found 10 hours ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Save 100% on your flight
Price was $4,220, price is now $2,791 per person
$2,791
per person
Nov 16 - Nov 21
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Sela V Hotel

Sela V Hotel

4 out of 5
Save 100% on your flight
Price was $1,689, price is now $1,147 per person
$1,147
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Wall Street Inn

The Wall Street Inn

3 out of 5
Save 100% on your flight
Price was $1,943, price is now $1,322 per person
$1,322
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Pestana CR7 Times Square

Pestana CR7 Times Square

4 out of 5
Save 100% on your flight
Price was $1,766, price is now $1,204 per person
$1,204
per person
Nov 23 - Nov 28
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
42 Hotel

42 Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,753, price is now $1,204 per person
$1,204
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)

6-7 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 $1,214, price is now $691 per person
$691
per person
Nov 17 - Nov 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Price was $5,517, price is now $3,208 per person
$3,208
per person
Dec 10 - Dec 16
found 6 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Park Lane New York

Park Lane New York

5 out of 5
Save 100% on your flight
Price was $3,211, price is now $1,932 per person
$1,932
per person
Nov 17 - Nov 24
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
Price was $4,974, price is now $3,039 per person
$3,039
per person
Dec 10 - Dec 16
found 6 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
Save 100% on your flight
Price was $3,303, price is now $2,034 per person
$2,034
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Kitano Hotel New York

The Kitano Hotel New York

4.5 out of 5
Price was $2,892, price is now $1,799 per person
$1,799
per person
Dec 10 - Dec 16
found 8 hours ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
The Wall Street Inn

The Wall Street Inn

3 out of 5
Price was $2,504, price is now $1,615 per person
$1,615
per person
Dec 2 - Dec 8
found 11 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 $4,004, price is now $2,593 per person
$2,593
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Royalton New York

Royalton New York

4 out of 5
Save 100% on your flight
Price was $1,326, price is now $873 per person
$873
per person
Nov 17 - Nov 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 $2,456, price is now $1,628 per person
$1,628
per person
Dec 10 - Dec 16
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
Nova Hotel JFK

Nova Hotel JFK

2 out of 5
Save 100% on your flight
Price was $1,413, price is now $946 per person
$946
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
Pestana CR7 Times Square

Pestana CR7 Times Square

4 out of 5
Save 100% on your flight
Price was $2,774, price is now $1,866 per person
$1,866
per person
Nov 27 - Dec 4
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.

Thu, Jan 7 - Sun, Jan 10
FLL
Fort Lauderdale
SWF
Newburgh
$96 Roundtrip, found 22 hours ago
$96
Roundtrip
found 22 hours ago
Select Allegiant Air flight, departing Thu, Jan 7 from Fort Lauderdale to Newburgh, returning Sun, Jan 10, priced at $96 found 22 hours ago
Fri, Nov 13 - Sun, Nov 15
MCO
Orlando
EWR
New York
$138 Roundtrip, found 1 day ago
$138
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Nov 13 from Orlando to New York, returning Sun, Nov 15, priced at $138 found 1 day ago
Wed, Jan 20 - Sun, Jan 24
MCO
Orlando
LGA
New York
$146 Roundtrip, found 4 hours ago
$146
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Wed, Jan 20 from Orlando to New York, returning Sun, Jan 24, priced at $146 found 4 hours 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
$210 nightly
The price is $237 total per night
$237 total
Nov 1 - Nov 2
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
Restaurant
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
$220 nightly
The price is $253 total per night
$253 total
Nov 10 - Nov 11
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
15.32 mi from city center
$77 nightly
The price is $89 total per night
$89 total
Oct 19 - Oct 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 Crystal Lake Town Park.
Pet friendly
Parking included
Don't see what you're looking for?
See all available properties in Southold
View all properties
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.