Southport Vacations

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Southport Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Inn at St John Portland In-Town

Inn at St John Portland In-Town

Valley Street
$778
per person
Oct 18 - Oct 24
found 6 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Thompson's Point and Cross Insurance Arena are located nearby.
Quiet place that feels like a trip into the past.

Reviewed on Sep 4, 2026

The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

Downtown Portland
Save 100% on your flight
$1,784
per person
Oct 18 - Oct 24
found 6 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Thompson's Point and Portland Head Light are located nearby.
Evalina Hotel

Evalina Hotel

Downtown Portland
Save 100% on your flight
$2,238
per person
Oct 18 - Oct 24
found 6 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions Cross Insurance Arena and Thompson's Point are located nearby.
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

Downtown Portland
Save 100% on your flight
$1,558
per person
Oct 18 - Oct 24
found 6 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Thompson's Point and Maine Mall are located nearby.
We had two amazing stays at Docent 178 and Docent 121. Beautiful apartments situated in the heart of Old Port, Portland. You are in walking distance to some of the best food found in Maine. The staff were also incredibly helpful and one text message away. Maine in the summer is expensive, but if you are going to spend on hotels anyway, might as well do it with Docent!

Reviewed on Aug 31, 2026

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

Downtown Portland
Save 100% on your flight
$1,982
per person
Oct 18 - Oct 24
found 6 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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 Cross Insurance Arena and Thompson's Point are located nearby.
AWOL Kennebunkport

AWOL Kennebunkport

Save 100% on your flight
$1,705
per person
Oct 18 - Oct 24
found 6 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Portland (PWM)
Stay at this 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 Wells Beach are located nearby.
The rooms were beautiful & very clean. Everything is planned and executed very thoughtfully by the staff. Breakfast was better than I could have imagined. We were only there one night on our way further up the coast but will be back to stay longer in the future.

Reviewed on Sep 2, 2026

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Southport Vacation Packages

Hoping to save time and money on your upcoming trip to Southport? The AARP Travel Center Powered by Expedia® can help you do both. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Southport perfect. With only a few clicks, you can select the best Southport vacation package for you and your family. AARP Travel Center has a huge selection of flights and lodgings, and local endeavors to pull from.

Hotels in Southport

With 1643 hotels and resorts in Southport to choose from, you will find one that is perfect for you.

From Southport hotels with multiple pools and on-site restaurants, to boutique accommodations that add all the extra amenities, you'll find a hotel here that will make your trip amazing. With AARP Travel Center's Southport hotel packages, you not only get a great rate on your flight, but also a great place to stay.

Things to do in Southport

Southport is the ideal place when you need to a break from it all. With only around 589 people here, this hidden-gem is just right for a quite vacation.

The AARP Travel Center "Things to Do" page has more great activities that you can book.

Package Your Southport Vacation and Save

With so much going on in Southport, you'll be wanting to focus on your outings, not spending time to searching for the hotel with the lowest rate. The AARP Travel Center Powered by Expedia® allows you to easily get everything you want, and save a little money. You can coordinate your whole trip, including things to do in Southport from only one place. So what are you waiting for? Bundle now and save!

Top Hotel Deals

Ocean Gate Inn

Ocean Gate Inn

70 Ocean Gate Rd Southport ME
0.68 km from city center
Stay at this hotel in Southport. Enjoy free breakfast, an outdoor pool, and a garden. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
Newagen Seaside Inn

Newagen Seaside Inn

60 Newagen Colony Southport ME
5.97 km from city center
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 ...
Flagship Inn and Suites

Flagship Inn and Suites

200 Townsend Avenue Boothbay Harbor ME
3.44 km from city center
Stay at this hotel in Boothbay Harbor. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the pool in our reviews. Popular ...
Residence Inn Bath Brunswick Area

Residence Inn Bath Brunswick Area

139 Richardson St. Bath ME
15.38 km from city center
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 ...
The Brunswick Hotel

The Brunswick Hotel

4 Noble St Brunswick ME
25.62 km from city center
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 ...
Travelers Inn

Travelers Inn

130 Pleasant St Brunswick ME
27.21 km from city center
Book a stay at this business-friendly motel in Brunswick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Spark by Hilton Brunswick

Spark by Hilton Brunswick

199 Pleasant St Brunswick ME
28.02 km from city center
Book a stay at this business-friendly hotel in Brunswick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Days Inn by Wyndham Brunswick Bath Area

Days Inn by Wyndham Brunswick Bath Area

224 Bath Rd Brunswick ME
21.62 km from city center
Book a stay at this business-friendly motel in Brunswick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Moonlight Inn

Moonlight Inn

215 Pleasant St Brunswick ME
28.41 km from city center
Stay at this motel in Brunswick. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Bluebird Ocean Point Inn

Bluebird Ocean Point Inn

191 Shore Road East Boothbay ME
5.02 km from city center
Stay at this hotel in East Boothbay. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Coastal Maine Botanical Gardens and Grimes Cove ...
Tugboat Inn

Tugboat Inn

80 Commercial St. Boothbay Harbor ME
2.54 km from city center
Stay at this hotel in Boothbay Harbor. Enjoy free WiFi, free parking, and a marina. Our guests praise the restaurant and the helpful staff in our reviews. Popular ...
Oceanfront Studio w/ Private Dock in Harpswell!

Oceanfront Studio w/ Private Dock in Harpswell!

Harpswell ME
22.74 km from city center
Stay at this apartment in Harpswell. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Mitchell Field and Bailey Island Bridge ...
Relax Inn

Relax Inn

133 Pleasant St Brunswick ME
27.19 km from city center
Book a stay at this business-friendly hotel in Brunswick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Fishermans Wharf Inn

Fishermans Wharf Inn

22 Commercial St Boothbay Harbor ME
2.7 km from city center
Stay at this hotel in Boothbay Harbor. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions Coastal ...
Topside Inn

Topside Inn

60 McKown St Boothbay Harbor ME
2.51 km from city center
Stay at this hotel in Boothbay Harbor. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Coastal Maine Botanical Gardens and Burnt Island ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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