South Portland Vacation Packages 2025/2026 from $395

South Portland flight + hotel vacation packages

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

Boston Lodge and Suites

Dorchester

Save 100% on your flight

$395

per person

Nov 8 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. Families will appreciate the playground, onsite laundry facilities, and in-room childcare. A hair salon, a picnic area, and express check-out are also on offer.

The McKernan Inn

Save 100% on your flight

$813

per person

Oct 29 - Nov 4

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Portland (PWM)

This inn features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A garden, a picnic area, and luggage storage are also on offer.

The Weldon Hotel

Downtown Portland

Save 100% on your flight

$755

per person

Nov 12 - Nov 17

found 23 hours ago

Roundtrip flight included

Denver (DEN) to Portland (PWM)

A 24-hour gym, self parking, and a virtual front desk are featured at this aparthotel. 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. Free WiFi in public areas is also provided.

The Westin Boston Seaport District

Seaport District

Save 100% on your flight

$680

per person

Nov 7 - Nov 11

found 1 day ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

The hotel's indoor pool, 24-hour gym, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the restaurant, hot tub, and laundry facilities.

Cliff House Maine

Save 100% on your flight

$993

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center, laundry service, and valet parking. Relax with a drink at one of the 2 poolside bars and enjoy perks like free self parking.

Top South Portland hotels deals

Germaine Inn South Portland

675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME

Free Cancellation

$85 nightly

$93 total

Oct 6 - Oct 7

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and WiFi in public areas. Enjoy the indoor pool and free perks like continental breakfast and free self parking.

Pool

Breakfast included

Days Inn by Wyndham Airport/Maine Mall

461 Maine Mall Rd, South Portland, ME

$899 nightly

$980 total

Sep 7 - Sep 8

Total with taxes and fees

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

Comfort Inn Airport

90 Maine Mall Rd, South Portland, ME

Free Cancellation

Reserve now, pay when you stay

$116 nightly

$127 total

Sep 9 - Sep 10

Total with taxes and fees

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.

Breakfast included

Free airport shuttle

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

80 John Roberts Rd., South Portland, ME

Free Cancellation

Reserve now, pay when you stay

$129 nightly

$141 total

Sep 7 - Sep 8

Total with taxes and fees

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

Tru by Hilton Portland Airport Area

369 Maine Mall Road, South Portland, ME

Free Cancellation

Reserve now, pay when you stay

$153 nightly

$167 total

Sep 10 - Sep 11

Total with taxes and fees

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.

Breakfast included

Free airport shuttle

DoubleTree by Hilton Hotel Portland

363 Maine Mall Rd, South Portland, ME

Free Cancellation

Reserve now, pay when you stay

$156 nightly

$170 total

Sep 10 - Sep 11

Total with taxes and fees

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.

Pool

Free airport shuttle

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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

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

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 great live music and acclaimed theater scene.

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 $395. 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.