Southport Vacation Packages
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Your Southport Vacation
Enjoy amazing adventures when you lock in a Southport vacation package. Whether you're a foodie, art enthusiast or just a traveler who loves to experience new places, there's something for everyone in this exciting city. A trip to Southport is a wonderful opportunity to see the sights. Be sure to visit popular attractions like Coastal Maine Botanical Gardens, Boothbay Harbor Marina and Cabbage Island. A few clicks is all it takes to craft your ideal Southport vacation on Expedia.
Top Southport Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
Downtown Portland
Price was CA $2,323, price is now CA $1,677 per person
CA $1,677
per person
May 16 - May 23
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.2/10 Wonderful! (1,765 reviews)
Nice place, clean room, courteous staff, NO FREE PARKING! :(
Reviewed on Feb 28, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was CA $2,848, price is now CA $2,179 per person
CA $2,179
per person
May 16 - May 23
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.6/10 Exceptional! (273 reviews)
Check-in and check-out are a breeze, easy access to a city parking lot on the block (needed as there was a snow ban on parking when I visited!). In terms of the space itself - clean, well appointed, spacious. Honestly a treat to stay here!
Reviewed on Feb 23, 2026
Inn By The Sea
Price was CA $3,207, price is now CA $2,501 per person
CA $2,501
per person
May 16 - May 23
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.4/10 Exceptional! (300 reviews)
Such a beautiful place, great to walk on beach, nice view, staff great.. cozy place.. so well decorated.. highly recommend for a nice quiet get away
Reviewed on Mar 4, 2026
Portland Regency Hotel & Spa
Downtown Portland
Price was CA $2,134, price is now CA $1,679 per person
CA $1,679
per person
May 16 - May 23
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.4/10 Exceptional! (1,587 reviews)
There was an unadvertised parking charge which was not included. Cleanliness was a little lacking. No hot tub or pool- and for a "nice" hotel it wasn't as nice as we'd hoped.
Reviewed on Mar 3, 2026
Southport Hotel Deals
Newagen Seaside Inn
60 Newagen Colony Southport ME
9.4/10 Exceptional! (341 reviews)
The staff was wonderful and the Inn is so beautiful with the water front setting!
Reviewed on Oct 22, 2025
The Federal
10 Water St Brunswick ME
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Mar 8 to Mar 9
CA $162
CA $176 total
Mar 8 - Mar 9
includes taxes & fees
9.6/10 Exceptional! (580 reviews)
Extremely cute and decor perfect for its era. Decorated for Christmas elegant. Comfy bed, amazing shower. Plenty of options for eating out in the area. Definitely want to visit again!
Reviewed on Mar 4, 2026
Fairfield Inn & Suites by Marriott Brunswick Freeport
36 Old Portland Rd Brunswick ME
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Mar 22 to Mar 23
CA $138
CA $151 total
Mar 22 - Mar 23
includes taxes & fees
8.8/10 Excellent! (447 reviews)
All of above
Reviewed on Feb 27, 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
