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Southport Vacation Packages

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Southport Flight + Hotel Packages

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

Portland Harbor Hotel

4 out of 5
Price was $325, price is now $234 per person
$234
per person
Jan 25 - Jan 27
found 12 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Fore Street Gallery are located nearby.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was $983, price is now $707 per person
$707
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Book a stay at this luxury resort in Cape Neddick. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Perkins Cove and Marginal Way are located nearby.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
Price was $422, price is now $304 per person
$304
per person
Jan 25 - Jan 27
found 12 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and concierge services. Popular attractions Victoria Mansion and Portland Club are located nearby.
The Docent's Collection - Boyd Block

The Docent's Collection - Boyd Block

2 out of 5
Price was $570, price is now $426 per person
$426
per person
Jan 16 - Jan 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Popular attractions Fore Street Gallery and Maine Sports Hall of Fame are located nearby.
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
Price was $623, price is now $469 per person
$469
per person
Jan 16 - Jan 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions Neal S. Dow House and Center for Cultural Exchange are located nearby.
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Price was $452, price is now $359 per person
$359
per person
Jan 16 - Jan 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions N.W. Barrett Gallery and Fore Street Gallery are located nearby.
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $517, price is now $415 per person
$415
per person
Jan 5 - Jan 8
found 1 hour ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Book a stay at this luxury hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dock Square and Kennebunkport Village Green are located nearby.
Inn By The Sea

Inn By The Sea

4 out of 5
Price was $419, price is now $347 per person
$347
per person
Jan 25 - Jan 27
found 12 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Book a stay at this luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.

Southport Vacation Packages 3-4 Night Stays

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

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $496, price is now $364 per person
$364
per person
Jan 5 - Jan 8
found 1 hour ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was $983, price is now $707 per person
$707
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $668, price is now $483 per person
$483
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
The Docent's Collection - Boyd Block

The Docent's Collection - Boyd Block

2 out of 5
Downtown Portland
Price was $734, price is now $534 per person
$534
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)

Southport Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was $811, price is now $605 per person
$605
per person
Dec 30 - Jan 4
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $1,396, price is now $1,014 per person
$1,014
per person
Dec 30 - Jan 4
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Price was $1,257, price is now $918 per person
$918
per person
Dec 30 - Jan 4
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $859, price is now $635 per person
$635
per person
Dec 30 - Jan 4
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)

Top Flight Deals

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

United
Mon, Dec 15 - Mon, Dec 15
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$171 Roundtrip, found 4 days ago
$171
Roundtrip
found 4 days ago
Select United flight, departing Mon, Dec 15 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Mon, Dec 15, priced at $171 found 4 days ago
Breeze Airways
Mon, Jan 5 - Fri, Jan 9
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$174 Roundtrip, found 2 hours ago
$174
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Mon, Jan 5 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Fri, Jan 9, priced at $174 found 2 hours ago
Breeze Airways
Mon, Dec 22 - Wed, Dec 31
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$178 Roundtrip, found 4 days ago
$178
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Mon, Dec 22 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Dec 31, priced at $178 found 4 days ago
Bargain Flight
Mon, Jan 12 - Wed, Jan 21
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$184 Roundtrip, found 23 hours ago
$184
Roundtrip
found 23 hours ago
Select Bargain Flight flight, departing Mon, Jan 12 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Jan 21, priced at $184 found 23 hours ago