South Portland Vacation Packages 2025 from $531

South Portland flight + hotel vacation packages

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

Studio Allston Hotel

Brighton

Save 100% on your flight

per person

Aug 1 - Aug 6

found 13 hours ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 3 conference rooms, free WiFi in public areas, and laundry service. Enjoy the free continental breakfast each morning.

Holly Tree Resort

Save 100% on your flight

per person

Aug 1 - Aug 8

found 23 hours ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

This aparthotel features an outdoor pool and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. There's a hot tub on site, and laundry facilities and barbecue grills are also offered.

The Inn at Hastings Park, Relais & Chateaux - Boston

Save 100% on your flight

per person

Aug 24 - Aug 30

found 17 hours ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

A restaurant and a bar/lounge are featured at this hotel. A terrace, limo/town car service, and a snack bar/deli are also on offer.

Sunbird ANNEX Resort

Save 100% on your flight

per person

Aug 1 - Aug 8

found 23 hours ago

Roundtrip flight included

Chicago (ORD) to Boston (BOS)

This hotel features an indoor pool and a seasonal outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Parker Beach Lodge

Bass River

Save 100% on your flight

per person

Aug 11 - Aug 18

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. Express check-in, express check-out, and luggage storage are also on offer.

Top South Portland hotels deals

Tru by Hilton Portland Airport Area

369 Maine Mall Road, South Portland, ME

Free Cancellation

Reserve now, pay when you stay

$112 nightly

$122 total

Jun 4 - Jun 5

Total includes 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

Comfort Inn Airport

90 Maine Mall Rd, South Portland, ME

Free Cancellation

Reserve now, pay when you stay

$85 nightly

$92 total

Jun 8 - Jun 9

Total includes 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

DoubleTree by Hilton Hotel Portland

363 Maine Mall Rd, South Portland, ME

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$101 total

Jun 9 - Jun 10

Total includes 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

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

80 John Roberts Rd., South Portland, ME

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$92 total

Jun 8 - Jun 9

Total includes 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

Quality Inn & Suites

738 Main Street, South Portland, ME

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$97 total

Jun 3 - Jun 4

Total includes taxes and fees

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

Best Western Merry Manor Inn

700 Main St, South Portland, ME

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$157 total

Jun 8 - Jun 9

Total includes taxes and fees

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.

Pool

Hot Tub

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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 acclaimed theater scene.

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 entertainment choices 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 $531. 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.