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 $1,882, price is now CA $1,369 per person
CA $1,369
per person
May 16 - May 21
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,776 reviews)
Very nice room, hotel was clean, staff kind and attentive. The location of thos hotel is great.
Reviewed on Mar 24, 2026
Blind Tiger Portland - Danforth Street.
West End
Price was CA $2,255, price is now CA $1,782 per person
CA $1,782
per person
May 16 - May 21
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (175 reviews)
The Blind Tiger was one of the best accommodations I've ever stayed in! The location was perfect – far enough away from the "bustle" of downtown but close enough to walk to many spots (Smalls was a favorite!). The daily breakfast was so great and the room, my goodness! Adorable, perfect, comfortable... best sleep of my life! Maggie was so helpful and accommodating and made our stay really special. All in all, highly recommend!
Reviewed on Mar 10, 2026
Portland Regency Hotel & Spa
Downtown Portland
Price was CA $1,717, price is now CA $1,372 per person
CA $1,372
per person
May 16 - May 21
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,599 reviews)
Our stay at Portland Regency Hotel and Spa was amazing. The staff greeted us with such warmth. Our room was exceptional and the food was superb.
Reviewed on Mar 22, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was CA $2,038, price is now CA $1,629 per person
CA $1,629
per person
May 16 - May 21
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (275 reviews)
Property is in an excellent location with so much to see and do (and eat) in walking distance. My room was clean, quiet, and well maintained. Staff interaction was minimal (by design) but the few times I spoke with the concierge on site she was pleasant and accommodating. My only negative comment is regarding the toiletry products. I’m a toilet paper snob and that angel soft just doesn’t cut it. Overall I am beyond satisfied with my stay and would absolutely stay here again.
Reviewed on Mar 22, 2026
The Weldon Hotel
Downtown Portland
Price was CA $2,170, price is now CA $1,788 per person
CA $1,788
per person
May 16 - May 21
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.8/10 Exceptional! (94 reviews)
The hotel is in an ideal location in downtown Portland. The staff is so kind and very accommodating! The stay was beyond comfortable and is the place we will stay every time we return to Portland!
Reviewed on Mar 23, 2026
Southport Hotel Deals
Stunning oceanfront cottage w/ private deck and Atlantic views
Southport ME
8.8/10 Excellent! (70 reviews)
This stay was a dream. As advertised. Would stay again. Easy directions, entry and had anything we needed. Drove as far as Acadia to hike and stayed local too. Even had a family emergency to ER (no fault of the property) and the Maine coastal ER care and service was fantastic. Thank you for the great ...
Reviewed on Oct 27, 2025
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
Ocean Gate Inn
70 Ocean Gate Rd Southport ME
8.6/10 Excellent! (1,000 reviews)
I loved it! It was a quick day trip, but we definitely will be back!!!
Reviewed on Oct 29, 2025
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.
