Book Exclusive Southport Vacation Packages

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Southport flight + hotel packages

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 CA $1,498, price is now CA $1,186 per person
CA $1,186
per person
Apr 30 - May 6
found 22 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) 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.
The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was CA $1,877, price is now CA $1,381 per person
CA $1,381
per person
Apr 30 - May 6
found 22 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Portland (PWM)
Book a stay at this luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Victoria Mansion and Charles Q. Clapp House are located nearby.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $2,288, price is now CA $1,742 per person
CA $1,742
per person
Apr 30 - May 6
found 22 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) 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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $1,613, price is now CA $1,247 per person
CA $1,247
per person
Apr 30 - May 6
found 22 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) 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.
Inn By The Sea

Inn By The Sea

4 out of 5
Price was CA $2,188, price is now CA $1,735 per person
CA $1,735
per person
Apr 30 - May 6
found 22 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) 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.

Top Southport hotels deals

Newagen Seaside Inn

Newagen Seaside Inn

3.5 out of 5
60 Newagen Colony Southport ME
Get rates
Book a stay at this family-friendly hotel in Southport. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Southport Memorial Library and Hendricks Hill Museum are located nearby.
Pool
Parking included
Beachfront Delight with detached guesthouse, private beach access, Dog-friendly

Beachfront Delight with detached guesthouse, private beach access, Dog-friendly

Southport ME
Get rates
Book a stay at this beach vacation home in Southport. Enjoy a beach locale, a garden, and patios. Popular attractions Hendricks Head Beach and Hendricks Head Light are located nearby.
Kitchen
Pet-friendly
The Federal

The Federal

2.5 out of 5
10 Water St Brunswick ME
Free cancellation
Reserve now, pay when you stay
The price is CA $161 per night
CA $161
CA $176 total
Feb 22 - Feb 23
includes taxes & fees
Stay at this hotel in Brunswick. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions West Island Gallery and Gulf of Maine are located nearby.
Pet-friendly
Parking included
Residence Inn Bath Brunswick Area

Residence Inn Bath Brunswick Area

3 out of 5
139 Richardson St. Bath ME
Free cancellation
Reserve now, pay when you stay
The price is CA $173 per night
CA $173
CA $188 total
Mar 1 - Mar 2
includes taxes & fees
Book a stay at this business-friendly hotel in Bath. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Markings Gallery and Waterfront Park are located nearby.
Pool
Breakfast included
Fairfield Inn & Suites by Marriott Brunswick Freeport

Fairfield Inn & Suites by Marriott Brunswick Freeport

2.5 out of 5
36 Old Portland Rd Brunswick ME
Free cancellation
Reserve now, pay when you stay
The price is CA $138 per night
CA $138
CA $150 total
Feb 22 - Feb 23
includes taxes & fees
Book a stay at this business-friendly hotel in Brunswick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Brunswick Golf Course and Androscoggin Swinging Bridge are located nearby.
Pool
Breakfast included
The Brunswick Hotel

The Brunswick Hotel

3 out of 5
4 Noble St Brunswick ME
Free cancellation
Reserve now, pay when you stay
Get rates
Book a stay at this business-friendly hotel in Brunswick. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions First Parish Church and Pickard Theater are located nearby.
Pet-friendly
Parking included
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See all available properties in Southport
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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.

Popular places to visit

Hendricks Head Beach

Why not spend a lazy afternoon at Hendricks Head Beach during your trip to Southport? Amble around this relaxing area's waterfront, or seek out the canoeing opportunities.

Hendricks Head Beach

Hendricks Hill Museum

You can spend time studying the exhibits at Hendricks Hill Museum during your travels in West Southport. While you're in the area, stroll along the waterfront.

Hendricks Hill Museum

Southport Memorial Library

Southport Memorial Library is just one of the places to see in Newagen, so why not enjoy the other things to explore during your travels? While you're in the area, stroll along the seaside.

Southport Memorial Library

Southport Vacations

Enjoy yourself more, worry less and wander wisely in Southport! Ensure your trip gets off to a superb start by finding out a few things about this unique destination.

You'll discover this Boothbay Harbor neighborhood 3 miles (5 kilometers) southwest of the downtown action.

Boothbay Harbor is home to some 1,000 residents.

Places to visit in Southport

Discover Hendricks Head Light, a long-standing building whose beam has guided vessels through thundering storms and crashing waves for many years. Want more ideas? History has plenty to teach us. Soak up the knowledge and better acquaint yourself with times past at Hendricks Hill Museum.

Where do you fly into for Southport?

Grab your luggage and passport and get set for one-of-a-kind experiences. When you touch down at Portland International Jetport Airport (PWM), you'll be just 35 miles (56 kilometers) west of Southport.

Frequently asked questions

How much are vacation packages to Southport?
With Travelocity vacation packages, you could paint the town red in Southport for as little as CA $1,186. Flights, tours and hotels — we have it all. You'll save tons just for combining your bookings. And with all that taken care of before you set off, you can sit back, relax and not worry about a thing.
How long should my Southport vacation be?
There's no hard and fast rule when it comes to how long your Southport vacation should be, but the majority of travelers like to stay for around 3 nights. Got some wiggle room in your departure date? Extend your escape by an extra night or two. That way, you'll have enough time to discover the area's hidden gems as well.
Where can I get the best vacation package deals for Southport?
Look no further than Travelocity. With access to 400 airline partners and an incredible 1,000,000 properties around the world, selecting the perfect Southport package deal couldn't be easier.
Why should I book my Southport vacation package via Travelocity?
With fantastic service, 24/7 support and some of the most gorgeous escapes around, you'll never wander alone. And if you happen to find a better price, we'll match it. That's our Price Match Guarantee.
Can I save money on my Southport car rental if I book it with hotels and flights?
With a Southport vacation package, you can combine your hotel, flight and car bookings and save some serious money. If you want to see the best of this wonderful part of the world, why not head to TD Garden? This well-known sight is 193 kilometers from Southport. With a rental car, you'll be there in a flash.
Which airport is best for Southport?
For many wanderers, a stay in Southport means strolling through arrivals at Portland Intl. Jetport Airport (PWM). This buzzing airport sits 56 kilometers west of the downtown area. You could also opt to fly into Knox County Regional Airport (RKD) (48 kilometers away from central Southport) or Augusta State Airport (AUG) (56 kilometers away from central Southport).
What is there to do in Southport?
While veering off the tourist trail can be rewarding, you really shouldn't miss the big sights that make a place famous. Hendricks Head Beach and Hendricks Head Light are a couple of them in Southport.
Where should I stay when visiting Southport?
Many visitors choose to check in to the Ocean Gate Resort. It's a great base for your Southport vacation.

Photos of local treasures

Browse Southport vacation photos for more inspiration

Cuckold Lighthouse built in 1896 at the entrance to Boothbay Harbor visible from the tip of Southport Island
Cuckold Lighthouse built in 1896 at the entrance to Boothbay Harbor visible from the tip of Southport Island
Southport Swing Bridge over Townsend Gut in Boothbay Harbor, Maine, USA
Maine Coast; Shutterstock ID 546441529; Purchase Order: -
I wandered up to Maine this summer and took in some ocean views. I hope to get back up there in the fall. #adventure #rainbow #maine #ocean #sunset