Cheap Vacations in Southold

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3-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
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Newark Liberty Intl. Airport (EWR)
The William Vale

The William Vale

5 out of 5
Save 100% on your flight
per person
Dec 16 - Dec 19
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
Fairfield Inn & Suites by Marriott Edison-South Plainfield

Fairfield Inn & Suites by Marriott Edison-South Plainfield

2.5 out of 5
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New York (NYC)
Sonesta Simply Suites Somerset

Sonesta Simply Suites Somerset

3 out of 5
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Newark Liberty Intl. Airport (EWR)
Howard Johnson by Wyndham North Plainfield

Howard Johnson by Wyndham North Plainfield

2 out of 5
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (NYC)
Hilton Newark Airport

Hilton Newark Airport

3.5 out of 5
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Newark Liberty Intl. Airport (EWR)
Doubletree by Hilton Somerset Hotel and Conference Center

Doubletree by Hilton Somerset Hotel and Conference Center

4 out of 5
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Newark Liberty Intl. Airport (EWR)
Motel 6 Piscataway, NJ

Motel 6 Piscataway, NJ

2 out of 5
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (NYC)
Motel 6 New Brunswick

Motel 6 New Brunswick

2 out of 5
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (NYC)
Clarion Hotel Somerset - New Brunswick

Clarion Hotel Somerset - New Brunswick

3.5 out of 5
per person
Dec 31 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Red Carpet Inn Edison

Red Carpet Inn Edison

2.5 out of 5
per person
Dec 31 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (NYC)
Extended Stay America Suites Piscataway Rutgers University

Extended Stay America Suites Piscataway Rutgers University

2.5 out of 5
per person
Dec 31 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (NYC)

4-night Southold vacations

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Hillsborough

Days Inn by Wyndham Hillsborough

2 out of 5
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Newark Liberty Intl. Airport (EWR)
The William Vale

The William Vale

5 out of 5
per person
Dec 14 - Dec 18
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New York (JFK)
Room H Divine Villa and Resorts

Room H Divine Villa and Resorts

2 out of 5
per person
Jan 2 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Newark Liberty Intl. Airport (EWR)
Room K Divine Villa and Resorts

Room K Divine Villa and Resorts

2 out of 5
per person
Jan 2 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Newark Liberty Intl. Airport (EWR)
Fidelia Room B

Fidelia Room B

2 out of 5
per person
Jan 3 - Jan 7
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Newark Liberty Intl. Airport (EWR)
Hilton Newark Airport

Hilton Newark Airport

3.5 out of 5
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Newark Liberty Intl. Airport (EWR)
Fairfield Inn & Suites Newark Liberty International Airport

Fairfield Inn & Suites Newark Liberty International Airport

2.5 out of 5
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Newark Liberty Intl. Airport (EWR)
Clarion Hotel Somerset - New Brunswick

Clarion Hotel Somerset - New Brunswick

3.5 out of 5
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Newark Liberty Intl. Airport (EWR)
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 3 - Jan 7
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
Room E Divine Villa 5mins to EWR

Room E Divine Villa 5mins to EWR

2 out of 5
per person
Jan 2 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Newark Liberty Intl. Airport (EWR)

5-night Southold vacations

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

Night Hotel Broadway

2.5 out of 5
Save 100% on your flight
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
per person
Dec 20 - Dec 25
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New York (JFK)
Millennium Hilton New York One UN Plaza

Millennium Hilton New York One UN Plaza

4 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
Hudson Yards Hotel

Hudson Yards Hotel

2 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 4
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New York (JFK)
Allegria Hotel

Allegria Hotel

4 out of 5
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New York (JFK)
Life Hotel New York

Life Hotel New York

3.5 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
Flushing Garden Hotel

Flushing Garden Hotel

2.5 out of 5
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
The Prince Kitano New York

The Prince Kitano New York

4.5 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)

6-7 night Southold vacations

Price found within the past 48 hours. Click for updated prices.
Comfort Suites Near University

Comfort Suites Near University

2.5 out of 5
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Newark Liberty Intl. Airport (EWR)
The William Vale

The William Vale

5 out of 5
per person
Dec 21 - Dec 27
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New York (JFK)
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
per person
Dec 21 - Dec 27
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New York (JFK)
Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New York (JFK)
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
Hyatt Regency Morristown

Hyatt Regency Morristown

4 out of 5
per person
Dec 20 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Mitchell Executive Hotel

Mitchell Executive Hotel

3.5 out of 5
per person
Dec 14 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
East Norwich Inn

East Norwich Inn

2.5 out of 5
per person
Dec 14 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
Millennium Hilton New York One UN Plaza

Millennium Hilton New York One UN Plaza

4 out of 5
Save 100% on your flight
per person
Dec 26 - Jan 1
found 4 hours ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
Hampton Inn Denville/Rockaway/Parsippany

Hampton Inn Denville/Rockaway/Parsippany

2.5 out of 5
per person
Dec 20 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (NYC)
Sonesta ES Suites Parsippany Morris Plains

Sonesta ES Suites Parsippany Morris Plains

3 out of 5
per person
Dec 20 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
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
Dec 21 - Dec 27
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New York (JFK)

Flight deals to Southold

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

Wed, Dec 18 - Mon, Jan 6
MIA
Miami
LGA
New York
$63 Roundtrip, found 2 days ago
$63
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Dec 18 from Miami to New York, returning Mon, Jan 6, priced at $63 found 2 days ago
Thu, Nov 21 - Fri, Nov 22
FLL
Fort Lauderdale
EWR
New York
$77 Roundtrip, found 6 days ago
$77
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Thu, Nov 21 from Fort Lauderdale to New York, returning Fri, Nov 22, priced at $77 found 6 days ago
Wed, Dec 4 - Wed, Dec 4
MCO
Orlando
LGA
New York
$83 Roundtrip, found 1 day ago
$83
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Dec 4 from Orlando to New York, returning Wed, Dec 4, priced at $83 found 1 day 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 $206 per night
$206
includes taxes & fees
$183 per night
Dec 15 - Dec 16
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
Free WiFi
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 15 - Dec 16
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.
Pool
Breakfast included
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
2.63 mi from city center
The price is $201 per night
$201
includes taxes & fees
$176 per night
Dec 2 - Dec 3
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.
On private beach
Pool
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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.