South Portland Vacation Packages 2025/2026 from $515

South Portland flight + hotel vacation packages

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

Riverview Resort

Bass River

Save 100% on your flight

per person

Sep 13 - Sep 16

found 4 hours ago

Roundtrip flight included

Nashville (BNA) to Boston (BOS)

This aparthotel features an indoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A 24-hour business center, a picnic area, and laundry facilities are also on offer.

Chebeague Island Inn

Save 100% on your flight

per person

Sep 1 - Sep 5

found 1 day ago

Roundtrip flight included

Nashville (BNA) to Portland (PWM)

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate perks like free WiFi and a free ferry terminal shuttle. A garden, a lobby fireplace, and a picnic area are also on offer.

Beacon Hill Hotel

Beacon Hill

Save 100% on your flight

per person

Sep 8 - Sep 14

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

This hotel features a restaurant, a rooftop terrace, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Free continental breakfast is served.

Encore Boston Harbor

Save 100% on your flight

per person

Aug 4 - Aug 9

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

This luxury hotel features a casino, a full-service spa, and a nightclub. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Free self parking is free for guests, and you can enjoy a meal in one of the 15 restaurants.

Boston Harbor Hotel

North End

Save 100% on your flight

per person

Aug 29 - Sep 1

found 1 day ago

Roundtrip flight included

Nashville (BNA) to Boston (BOS)

A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.

Top South Portland hotels deals

Days Inn by Wyndham Airport/Maine Mall

461 Maine Mall Rd, South Portland, ME

Free Cancellation

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This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Casco Bay Hotel Portland Airport - Maine Mall, Ascend Hotel Collection

80 John Roberts Rd., South Portland, ME

Free Cancellation

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This hotel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free airport shuttle. Business travelers can take advantage of the free WiFi in public areas. There's a gym on site, and a 24-hour front desk and dry cleaning are also provided.

Breakfast included

Free airport shuttle

DoubleTree by Hilton Hotel Portland

363 Maine Mall Rd, South Portland, ME

Free Cancellation

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This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free self parking and a free airport shuttle. A business center, a coffee shop, and free WiFi in public areas are also on offer.

Tru by Hilton Portland Airport Area

369 Maine Mall Road, South Portland, ME

Free Cancellation

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This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free self parking, and a free airport shuttle. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Comfort Inn Airport

90 Maine Mall Rd, South Portland, ME

Free Cancellation

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This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and a free airport shuttle. Traveling on business? Take advantage of the express check-out, laundry service, and free train station pick-up. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Quality Inn & Suites

738 Main Street, South Portland, ME

Free Cancellation

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This hotel features free WiFi in public areas, free newspapers, and free self parking. Enjoy the free continental breakfast each morning. A garden and a picnic area are also provided.

Breakfast included

Pet friendly

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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

Bug Light

4.5/5(44 reviews)

You can find out about the history of South Portland with a visit to Bug Light. Experience the area's great live music and entertainment choices.

Southern Maine Community College

Walk around the campus at Southern Maine Community College as part of your travels around South Portland. Amble around this family-friendly area's waterfront and enjoy its top-notch restaurants.

Fort Preble

Find out about the history of South Portland when you take a trip to Fort Preble. Experience the area's acclaimed theater scene and entertainment choices.

Frequently asked questions

How much are vacation packages to South Portland?

Vacation packages, which include flights and hotels in South Portland, start from as little as $515. Make your travel dreams a reality and secure your dream vacation with Travelocity today.

How long should my South Portland vacation be?

Generally, people spend 2 nights in South Portland. But that mightn't be long enough for you. If you'd like to explore some of the region's off-the-beaten-path gems, why not add a few extra nights to your travel itinerary?

Where can I get the best vacation package deals for South Portland?

For a fun and affordable South Portland package deal, head straight to Travelocity. Choose from 400 partner airlines and 1,000,000 properties around the globe to create your ultimate adventure --- you're spoiled for choice!

Why should I purchase my South Portland vacation bundle with Travelocity?

Because we believe in creating special travel experiences. From hotels and flights to car rentals and activities, everything is at your fingertips. Our customer support team is available 24/7 to ensure you'll never roam alone. We also have a Price Match Guarantee, so you can book your trip knowing you've scored the best deal around.

Will I save money on my South Portland car rental if I bundle it with hotels and flights?

Certainly --- combine your hotel, car and flight into a South Portland vacation package and you can save plenty. With so much to see in South Portland, that set of wheels will make exploring a breeze. Once you've slid into the driver's seat, hit the wide open road and make your way to Fenway Park, a famous attraction roughly 100 mi from South Portland.

Which airport is best for South Portland?

Portland Intl. Jetport Airport (PWM), 4 mi west of the city center, is where many visitors begin their South Portland adventures. That said, Augusta State Airport (AUG) (50 mi away from central South Portland) could suit you better.

What is there to do in South Portland?

South Portland is full of sights to check out, including Maine Mall and Willard Beach. These two popular attractions are on most visitors' itineraries.

Where should I stay when visiting South Portland?

The Casco Bay Hotel, Ascend Hotel Collection is the top choice of many travelers. Book as soon as possible to avoid missing out.