Deals on vacations and trips to South Portland

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South Portland flight + hotel vacation packages

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

Sunbird ANNEX Resort

2 out of 5
Save 100% on your flight
Price was $635, price is now $433 per person
$433
per person
Jun 29 - Jul 3
found 1 day 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.
Briar Barn Inn

Briar Barn Inn

3.5 out of 5
Save 100% on your flight
Price was $2,421, price is now $1,559 per person
$1,559
per person
Jun 4 - Jun 8
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
This smoke-free hotel features a full-service spa and a restaurant. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking. There's a bar/lounge on site, and a 24-hour front desk and wedding services are also provided.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,423, price is now $919 per person
$919
per person
May 29 - Jun 1
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Boston (BOS)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the 24-hour gym and perks like free WiFi.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $2,186, price is now $1,451 per person
$1,451
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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.
The Mansion at Ocean Edge

The Mansion at Ocean Edge

4 out of 5
Save 100% on your flight
Price was $2,094, price is now $1,403 per person
$1,403
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
This smoke-free hotel features a private beach, a golf course, and a full-service spa. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities. Enjoy the 3 outdoor pools and get free self parking.

Top South Portland hotels deals

DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
363 Maine Mall Rd South Portland ME
Free Cancellation
Reserve now, pay when you stay
$81 nightly
The price is $88 total per night
$88 total
Apr 26 - Apr 27
Total with taxes and fees
This hotel features a restaurant, an outdoor 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
Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

2.5 out of 5
90 Maine Mall Rd South Portland ME
Free Cancellation
$74 nightly
The price is $81 total per night
$81 total
Apr 29 - Apr 30
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
Spark by Hilton Portland Airport Maine Mall

Spark by Hilton Portland Airport Maine Mall

2 out of 5
461 Maine Mall Rd South Portland ME
Free Cancellation
Reserve now, pay when you stay
$68 nightly
The price is $74 total per night
$74 total
Apr 23 - Apr 24
Total with taxes and fees
This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free airport shuttle. Enjoy the 24-hour gym and free perks like continental breakfast and free self parking.
Pool
Breakfast included
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

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

3.5 out of 5
80 John Roberts Rd. South Portland ME
Free Cancellation
$76 nightly
The price is $82 total per night
$82 total
Apr 26 - Apr 27
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
Long Creek Hotel by IHG

Long Creek Hotel by IHG

2.5 out of 5
171 Philbrook Ave South Portland ME
Free Cancellation
$77 nightly
The price is $84 total per night
$84 total
May 18 - May 19
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like on-the-go breakfast and free self parking.
Pool
Hot Tub
Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

3 out of 5
369 Maine Mall Road South Portland ME
Free Cancellation
Reserve now, pay when you stay
$81 nightly
The price is $88 total per night
$88 total
Apr 29 - Apr 30
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
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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

Southern Maine Community College

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.

Southern Maine Community College
South Portland, Maine, USA at the Portland Breakwater Light.; Shutterstock ID 688189870; Purchase Order: -

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.

Bug Light
Fort Preble

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.

Fort Preble

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 $433. 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.

Photos of local treasures

Browse South Portland vacation photos for more inspiration

Portland Head Lighthouse
Portland Breakwater Lighthouse at sunset - Bug Light Park - South Portland, Maine.
Portland Harbor aerial view from Eastern Promenade in East End, city of Portland, Maine ME, USA.
Fishing Shack at Willard Beach in South Portland, Maine USA
H3M0PA South Portland, Maine, USA at the Portland Breakwater Light.