Vacations to South Portland

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Your South Portland Vacation

With one of our vacation packages to South Portland, you'll discover infinite opportunities for fun and relaxation. There's so much to enjoy, including its coastal scenery and lively atmosphere. If your trip to South Portland includes a little sightseeing, drop by much-loved attractions like Portland Head Light, University of Southern Maine and Portland Museum of Art. A couple of quick clicks is all it takes to put together a tailored South Portland vacation on Expedia.

Top South Portland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Global Luxury Suites East Boston

Global Luxury Suites East Boston

4 out of 5
East Boston
Save 100% on your flight
per person
Aug. 8 - Aug. 11
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
7/10 Good! (83 reviews)
It was very important that I called a week ahead to pay for parking and to make sure a lockbox was ready for us when we arrived after midnight when no one was at the main desk. I had to call again before we got on the plane for our lock box code. It was close to the subway entrance. The pool was in a different building and it was closed for maintenance. The main reason I picked this location was the pool for our son, he was very disappointed.

Reviewed on Apr. 23, 2024

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jul. 18 - Jul. 21
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (269 reviews)
Great property great service

Reviewed on May 5, 2024

YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
Save 100% on your flight
per person
Jul. 26 - Jul. 30
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
8.2/10 Very Good! (1,662 reviews)
Room was clean and well appointed. Staff was courteous. Fine for our short stay (1 night) but room was extremely small.

Reviewed on May 11, 2024

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jul. 18 - Jul. 21
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (31 reviews)
My stay was lovely. In ordering a cheese plate to await my arrival, a friend alerted the staff that it was my birthday. When I entered my very handsome room, a gorgeous little chocolate bday cake, under domed glass, sat waiting for me. Otherwise, the staff was incredibly attentive, the speakeasy was fun for a delicious cocktail, and the overall atmosphere was one of restrained indulgence. The place doesn’t feel ostentatious. Its elegance was much more understated. I loved it

Reviewed on Apr. 28, 2024

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
Jul. 18 - Jul. 21
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (2,220 reviews)
I loved the room which was spacious, clean and very comfortable.

Reviewed on May 15, 2024

Where to stay in South Portland

Find the best South Portland areas and neighborhoods for the activities you enjoy most. Learn more about South Portland
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Willard

While Willard might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Willard Beach and Victoria Mansion.

Find hotel + flight trips in Willard

South Portland Beach Vacation

Live out those beachy daydreams on your South Portland vacation. Embark on a romantic walk, admire the spectacular coastal vistas and collect pretty seashells during your trip to South Portland. Situated just 5 kilometres from the city center, Willard Beach is the place to be for many sun-seeking visitors. Look through our South Portland vacation deals and watch your travel budget stretch further!

South Portland Hotel Deals

Casco Bay Hotel, Ascend Hotel Collection
Casco Bay Hotel, Ascend Hotel Collection
3.5 out of 5
80 John Roberts Rd., South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from May 20 to May 21
CA $134
CA $146 total
includes taxes & fees
May 20 - May 21
8.6/10 Excellent! (1,459 reviews)
"Very convenient, fairly priced, and roomy. Would def stay again."

Reviewed on May 12, 2024

Casco Bay Hotel, Ascend Hotel Collection
Comfort Inn Airport
Comfort Inn Airport
2.5 out of 5
90 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from May 16 to May 17
CA $123
CA $134 total
includes taxes & fees
May 16 - May 17
8.2/10 Very Good! (1,007 reviews)
"Just a bed for the night. Room okay. Mediocre accommodations. Convenient to the airport."

Reviewed on May 13, 2024

Comfort Inn Airport
DoubleTree by Hilton Hotel Portland
DoubleTree by Hilton Hotel Portland
4 out of 5
363 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $166 per night from May 19 to May 20
CA $166
CA $180 total
includes taxes & fees
May 19 - May 20
8/10 Very Good! (1,003 reviews)
Housekeeping needs vary
"I love staying at this DoubleTree. The location is ideal, the hotel is nice but the best part is the Front Desk Employees. They are welcoming and always helpful. I do appreciate the Shuttle service. They didn't service my room during the 4 days I was there. I put my trash outside, and had to ask ..."

Reviewed on May 6, 2024

DoubleTree by Hilton Hotel Portland
See all 2,409 properties in South Portland
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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

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Beach Vacations

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Frequently asked questions

How much does a South Portland vacation package cost?
The cheapest South Portland vacation package is CA $897, so your dream escape can become a reality — without breaking the bank. Bundle flights, hotels, car rentals and more to tailor make a package that suits you.
How do I get a cheap travel package to South Portland?
Track down flights that suit your busy schedule, add a hotel room to your booking and watch the savings stack up with a South Portland vacation package. It’s that easy! From flights and hotels to rental cars and activities, Expedia makes traveling cheaply a cinch. And with more than 550 air carriers and 1,000,000 hotels throughout the world to select from, you’ll never be short of choice.
Where should I stay in South Portland?
With fascinating attractions like Portland Head Light and University of Southern Maine in this area, try to find a hotel near either of them. Portland Museum of Art is another sight that people flock to.
What are the top hotels in South Portland?
If you intend to stay in the Willard neighborhood, some great options are Casco Bay Hotel, Ascend Hotel Collection and DoubleTree by Hilton Hotel Portland. Willard Beach is another well-known South Portland area. We recommend Tru by Hilton Portland Airport Area or Hampton Inn Portland Airport if you choose this part of the city.
How far in advance should I book my South Portland vacation?
Your safest bet is to book early. Air carriers typically advertise flights nearly 12 months ahead of departure, and this is a fantastic opportunity to pick up some of the cheapest prices. Boss just told you to use up some vacation time next month? No need to worry. Expedia are never short of fantastic deals to help you have the getaway of your dreams, at an affordable price.
What does an Expedia South Portland travel package include?
From flights and hotels to car rentals, Expedia can help you craft a South Portland package that works for you. Heading away for a week or longer? Consider a hotel, rental car and flight bundle. If you’re taking a quick break, a hotel and flight deal could be what you’re after. Experiences can also be added once you’ve made your booking. Our vacation packages make it easy to save and plan.
What should I know before booking a South Portland travel package?
Bundling your bookings into a South Portland vacation package is the easiest way to organize your trip. Not only that, you’ll save just for combining your hotels, flights and car rentals. Once you’ve booked, why not add on a tour or an activity?
Can I choose my airline with a South Portland Expedia vacation package?
With a vacation package, you’re in charge. Whether you want to fly to South Portland in coach or business class, simply select from the available airline options. Expedia has access to more than 550 airline partners all over the world.
If I'm not able to travel, can I cancel my South Portland vacation package?
It’s impossible to predict what tomorrow might bring, so it’s comforting to know that you can cancel or change your South Portland vacation package. If you made your booking in the last 24 hours, you may be entitled to a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Check our Customer Service Portal to learn more.

Discover the most popular places to visit in South Portland

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Bug Light

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

Bug Light
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Fort Preble

On the South Portland waterfront, survey the scene of the Battle of Portland Harbor, which is the only known Civil War conflict fought in Maine.

Fort Preble
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Maine Mall

4/5(64 reviews)

You can do some window-shopping at Maine Mall during your visit to South Portland. Experience the area's entertainment choices and great live music.

Maine Mall

What to do in South Portland

Image for Half Day Private Boat Charter from Portland

Half Day Private Boat Charter from Portland

CA $880
Per adult
Half Day Private Boat Charter from Portland
Image for Portland: Old Port Seafood Lovers Tour

Portland: Old Port Seafood Lovers Tour

CA $198
Per adult
Portland: Old Port Seafood Lovers Tour
Image for Self-Guided Driving & Walking Bundle of Portland Maine Tours

Self-Guided Driving & Walking Bundle of Portland Maine Tours

CA $23
Per adult
100% of travellers recommend
Self-Guided Driving & Walking Bundle of Portland Maine Tours
See all activities in South Portland

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.