Cheap Vacations in Southold

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3-night Southold vacations

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

The Heldrich Hotel

4 out of 5
Save 100% on your flight
per person
Jan 17 - Jan 20
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
The William Vale

The William Vale

5 out of 5
per person
Jan 7 - Jan 10
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
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The New York EDITION

The New York EDITION

5 out of 5
Save 100% on your flight
per person
Dec 30 - Jan 2
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
per person
Jan 5 - Jan 8
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
per person
Jan 5 - Jan 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Save 100% on your flight
per person
Jan 5 - Jan 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Michelangelo Hotel

The Michelangelo Hotel

4 out of 5
Save 100% on your flight
per person
Jan 16 - Jan 19
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
Jan 4 - Jan 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Evelyn Hotel

The Evelyn Hotel

4.5 out of 5
Save 100% on your flight
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Westin New York at Times Square

The Westin New York at Times Square

4.5 out of 5
Save 100% on your flight
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Iroquois New York

The Iroquois New York

4.5 out of 5
Save 100% on your flight
per person
Jan 16 - Jan 19
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.
Little Charlie Hotel

Little Charlie Hotel

2 out of 5
Save 100% on your flight
per person
Jan 18 - Jan 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The William Vale

The William Vale

5 out of 5
per person
Jan 1 - Jan 5
found 24 hours ago
Roundtrip non-stop 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
per person
Jan 16 - Jan 20
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
Jan 3 - Jan 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Westgate New York Grand Central

Westgate New York Grand Central

4 out of 5
Save 100% on your flight
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Save 100% on your flight
per person
Jan 1 - Jan 5
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to New York (JFK)
The New York EDITION

The New York EDITION

5 out of 5
Save 100% on your flight
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Motel Casa Downtown Guest House

Motel Casa Downtown Guest House

3 out of 5
per person
Dec 26 - Dec 30
found 7 hours 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
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Westin New York at Times Square

The Westin New York at Times Square

4.5 out of 5
Save 100% on your flight
per person
Dec 30 - Jan 3
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
per person
Jan 1 - Jan 5
found 24 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to New York (JFK)
Hotel St. James

Hotel St. James

2.5 out of 5
Save 100% on your flight
per person
Jan 3 - Jan 7
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.
Aura Hotel Times Square

Aura Hotel Times Square

4 out of 5
Save 100% on your flight
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New York (JFK)
The William Vale

The William Vale

5 out of 5
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Heart of New York Suites

Heart of New York Suites

2 out of 5
per person
Dec 25 - Dec 30
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
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New York (JFK)
Westgate New York Grand Central

Westgate New York Grand Central

4 out of 5
Save 100% on your flight
per person
Dec 25 - Dec 30
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
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Pendry Manhattan West

Pendry Manhattan West

5 out of 5
Save 100% on your flight
per person
Dec 25 - Dec 30
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
Save 100% on your flight
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Manner

The Manner

5 out of 5
Save 100% on your flight
per person
Jan 8 - Jan 13
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Westin New York at Times Square

The Westin New York at Times Square

4.5 out of 5
Save 100% on your flight
per person
Dec 29 - Jan 3
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
Jan 1 - Jan 6
found 1 day ago
Roundtrip non-stop 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
per person
Jan 19 - Jan 24
found 12 hours 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.
Motel Casa Downtown Guest House

Motel Casa Downtown Guest House

3 out of 5
Save 100% on your flight
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
The William Vale

The William Vale

5 out of 5
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Heart of New York Suites

Heart of New York Suites

2 out of 5
per person
Dec 27 - Jan 2
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
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Hotel Edison Times Square

Hotel Edison Times Square

4 out of 5
Save 100% on your flight
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Save 100% on your flight
per person
Dec 29 - Jan 4
found 9 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to New York (JFK)
Hotel Hugo

Hotel Hugo

4.5 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 2
found 14 hours ago
Roundtrip flight included
Dallas (DFW) 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
per person
Jan 7 - Jan 14
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
CODA Williamsburg

CODA Williamsburg

4 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
Save 100% on your flight
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Michelangelo Hotel

The Michelangelo Hotel

4 out of 5
Save 100% on your flight
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
The Herald by LuxUrban

The Herald by LuxUrban

2.5 out of 5
Save 100% on your flight
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)

Flight deals to Southold

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

Mon, Mar 10 - Mon, Mar 17
MCO
Orlando
HVN
New Haven
$82 Roundtrip, found 1 day ago
$82
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Mar 10 from Orlando to New Haven, returning Mon, Mar 17, priced at $82 found 1 day ago
Wed, Dec 11 - Tue, Dec 17
MIA
Miami
EWR
New York
$83 Roundtrip, found 4 days ago
$83
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Dec 11 from Miami to New York, returning Tue, Dec 17, priced at $83 found 4 days ago
Thu, Dec 5 - Sun, Dec 8
MCO
Orlando
SWF
Newburgh
$84 Roundtrip, found 5 days ago
$84
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Dec 5 from Orlando to Newburgh, returning Sun, Dec 8, priced at $84 found 5 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 $215 per night
$215
includes taxes & fees
$191 per night
Dec 9 - Dec 10
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.
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Free Cancellation
Reserve now, pay when you stay
17.88 mi from city center
The price is $88 per night
$88
includes taxes & fees
$77 per night
Dec 10 - Dec 11
A stay at Quality Inn Old Saybrook - Westbrook places you in the heart of Old Saybrook, a 5-minute drive from Essex Steam Train and 5 minutes from Essex Library.
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 $76 per night
$76
includes taxes & fees
$66 per night
Dec 1 - Dec 2
Located in Old Saybrook (Saybrook Manor), Pier Blue Inn Old Saybrook - Essex is within a 5-minute drive of Chalker Beach and Saybrook Country Barn.
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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.