Cheap Vacations in Southold

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3-night Southold vacations

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

Flushing Garden Hotel

2.5 out of 5
per person
Jul 12 - Jul 15
found 15 hours ago
Roundtrip flight included
Tampa (TPA) to New York (JFK)
Chelsea Pines Inn

Chelsea Pines Inn

2.5 out of 5
per person
Jul 12 - Jul 15
found 15 hours ago
Roundtrip flight included
Tampa (TPA) to New York (JFK)
Hudson River Hotel

Hudson River Hotel

2.5 out of 5
per person
Jul 12 - Jul 15
found 15 hours ago
Roundtrip flight included
Tampa (TPA) 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
per person
Jul 11 - Jul 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
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Save 100% on your flight
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
RIU Plaza Manhattan Times Square

RIU Plaza Manhattan Times Square

4 out of 5
Save 100% on your flight
per person
Jun 27 - Jun 30
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
per person
Jun 27 - Jun 30
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
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Dominick

The Dominick

5 out of 5
Save 100% on your flight
per person
Jun 25 - Jun 28
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Holiday Inn Express - New York City Chelsea, an IHG Hotel

Holiday Inn Express - New York City Chelsea, an IHG Hotel

3 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New York (JFK)
The Benjamin Royal Sonesta New York

The Benjamin Royal Sonesta New York

4.5 out of 5
Save 100% on your flight
per person
Jul 2 - Jul 5
just found
Roundtrip flight included
Atlanta (ATL) to New York (JFK)

4-night Southold vacations

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

Chelsea Savoy Hotel

2 out of 5
Save 100% on your flight
per person
Jul 12 - Jul 16
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Hyatt Herald Square New York

Hyatt Herald Square New York

4 out of 5
Save 100% on your flight
per person
Jul 11 - Jul 15
found 24 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to New York (JFK)
Holiday Inn Express New York City- Wall Street, an IHG Hotel

Holiday Inn Express New York City- Wall Street, an IHG Hotel

2.5 out of 5
Save 100% on your flight
per person
Jul 11 - Jul 15
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
New York Marriott Marquis

New York Marriott Marquis

4.5 out of 5
Save 100% on your flight
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Save 100% on your flight
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
RIU Plaza Manhattan Times Square

RIU Plaza Manhattan Times Square

4 out of 5
Save 100% on your flight
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Home2 Suites By Hilton New York Times Square

Home2 Suites By Hilton New York Times Square

3 out of 5
Save 100% on your flight
per person
Jul 12 - Jul 16
found 19 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
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Plaza - A Fairmont Managed Hotel

The Plaza - A Fairmont Managed Hotel

5 out of 5
Save 100% on your flight
per person
Jul 18 - Jul 22
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
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Carlyle, A Rosewood Hotel

The Carlyle, A Rosewood Hotel

5 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to New York (JFK)

5-night Southold vacations

Price found within the past 48 hours. Click for updated prices.
Citadines Connect Fifth Avenue New York

Citadines Connect Fifth Avenue New York

3.5 out of 5
Save 100% on your flight
per person
Jul 11 - Jul 16
found 5 hours ago
Roundtrip flight included
Orlando (MCO) 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
per person
Jul 11 - Jul 16
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
per person
Jul 17 - Jul 22
found 22 hours ago
Roundtrip non-stop 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
per person
Jul 11 - Jul 16
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
RIU Plaza Manhattan Times Square

RIU Plaza Manhattan Times Square

4 out of 5
Save 100% on your flight
per person
Jul 11 - Jul 16
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Sanctuary Hotel New York

Sanctuary Hotel New York

4.5 out of 5
Save 100% on your flight
per person
Jul 11 - Jul 16
found 5 hours ago
Roundtrip flight included
Orlando (MCO) to New York (JFK)
The Lexington Hotel, Autograph Collection

The Lexington Hotel, Autograph Collection

4 out of 5
Save 100% on your flight
per person
Jul 3 - Jul 8
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to New York (JFK)
Club Quarters, Times Square - Midtown

Club Quarters, Times Square - Midtown

4 out of 5
Save 100% on your flight
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New York (JFK)
Hotel St. James

Hotel St. James

2.5 out of 5
per person
Jul 11 - Jul 16
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Hard Rock Hotel New York

Hard Rock Hotel New York

4.5 out of 5
Save 100% on your flight
per person
Jul 11 - Jul 16
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Millennium Premier New York Times Square

Millennium Premier New York Times Square

4 out of 5
Save 100% on your flight
per person
Jul 17 - Jul 22
found 22 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
Hyatt Centric Times Square New York

Hyatt Centric Times Square New York

4.5 out of 5
per person
Jul 11 - Jul 16
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)

6-7 night Southold vacations

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express - New York City Chelsea, an IHG Hotel

Holiday Inn Express - New York City Chelsea, an IHG Hotel

3 out of 5
Save 100% on your flight
per person
Jun 25 - Jul 1
found 19 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
LaGuardia Plaza Hotel

LaGuardia Plaza Hotel

4 out of 5
Save 100% on your flight
per person
Jun 29 - Jul 6
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New York (NYC)
voco Fiorello - LaGuardia East, an IHG Hotel

voco Fiorello - LaGuardia East, an IHG Hotel

4 out of 5
Save 100% on your flight
per person
Jun 29 - Jul 6
found 1 day ago
Roundtrip flight included
Tampa (TPA) 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
per person
Jul 3 - Jul 9
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
New York Marriott Marquis

New York Marriott Marquis

4.5 out of 5
Save 100% on your flight
per person
Jul 3 - Jul 9
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
The Chatwal, In The Unbound Collection By Hyatt

The Chatwal, In The Unbound Collection By Hyatt

5 out of 5
Save 100% on your flight
per person
Jun 29 - Jul 5
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Save 100% on your flight
per person
Jul 3 - Jul 9
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
RIU Plaza Manhattan Times Square

RIU Plaza Manhattan Times Square

4 out of 5
Save 100% on your flight
per person
Jul 3 - Jul 9
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Home2 Suites By Hilton New York Times Square

Home2 Suites By Hilton New York Times Square

3 out of 5
Save 100% on your flight
per person
Jun 25 - Jul 1
found 19 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
Library Hotel by Library Hotel Collection

Library Hotel by Library Hotel Collection

4 out of 5
Save 100% on your flight
per person
Jun 29 - Jul 5
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New York (JFK)
Hotel St. James

Hotel St. James

2.5 out of 5
per person
Jul 3 - Jul 9
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Hard Rock Hotel New York

Hard Rock Hotel New York

4.5 out of 5
per person
Jul 3 - Jul 9
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.

Tue, Jun 4 - Wed, Jun 12
FLL
Fort Lauderdale
EWR
Newark
$51 Roundtrip, found 21 hours ago
$51
Roundtrip
found 21 hours ago
Select Spirit Airlines flight, departing Tue, Jun 4 from Fort Lauderdale to Newark, returning Wed, Jun 12, priced at $51 found 21 hours ago
Tue, Jun 4 - Wed, Jun 5
FLL
Fort Lauderdale
LGA
New York
$63 Roundtrip, found 3 days ago
$63
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Jun 4 from Fort Lauderdale to New York, returning Wed, Jun 5, priced at $63 found 3 days ago
Thu, Jun 6 - Tue, Jun 11
MIA
Miami
LGA
New York
$73 Roundtrip, found 4 days ago
$73
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Thu, Jun 6 from Miami to New York, returning Tue, Jun 11, priced at $73 found 4 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
The price is $295 per night
$295
per night
May 29 - May 30
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.
Breakfast included
Restaurant
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

3 out of 5
2038 Old Country Rd, Riverhead, NY
Free Cancellation
Reserve now, pay when you stay
18.01 mi from city center
The price is $132 per night
$132
per night
May 30 - May 31
With a stay at Hilton Garden Inn Riverhead, you'll be centrally located in Riverhead, within a 5-minute drive of Splish Splash Water Park and Out East Family Fun.
Pool
Pet friendly
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
The price is $89 per night
$89
per night
May 26 - May 27
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.
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.