South Portland Vacation Packages

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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.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

CA $1,366
per person
Oct 1 - Oct 4
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (262 reviews)
Good Hotels Boston

Good Hotels Boston

South End
CA $1,402
per person
Sep 23 - Sep 26
found 24 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
8/10 Very good! (55 reviews)
Very nice people and had excellent help!

Reviewed on Aug 7, 2026

Mandarin Oriental, Boston

Mandarin Oriental, Boston

Back Bay
CA $2,971
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to Boston (BOS)
9.4/10 Exceptional! (440 reviews)
Four Seasons Hotel Boston

Four Seasons Hotel Boston

Bay Village
CA $2,654
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (475 reviews)
Overrated

Reviewed on Aug 10, 2026

Raffles Boston

Raffles Boston

Back Bay
CA $3,559
per person
Oct 19 - Oct 23
found 20 hours ago
Roundtrip flight included
Calgary (YYC) to Boston (BOS)
9.6/10 Exceptional! (285 reviews)
Can't wait for my next excuse to return

Reviewed on Aug 14, 2026

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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Ferry Village

1 out of top 10 points of interest in this area

While there might not be top attractions in Ferry Village, you can explore the larger area and discover places like Bug Light and Willard Beach.

A lighthouse on a rocky breakwater, a large building across the water, and a clear sky.

Willard Beach

2 out of top 10 points of interest in this area

If you're looking for some top things to see and do in Willard Beach and surrounding area, you can visit Willard Beach and Bug Light.

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Ligonia

When in Ligonia, you can plan a visit to Thompson's Point and Hadlock Field, some noteworthy sights in the nearby area.

Two people sitting on a red bench outside a bakery with a sign that reads "Scratch Baking Co."

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 Bug Light.

A coastal cityscape with a marina, buildings, and a clear blue sky.

Knightville

When in Knightville, you can plan a visit to Victoria Mansion and Portland Museum of Art, some noteworthy sights in the nearby area.

South Portland Beach Vacation

Listen to the soothing sound of waves rolling into the shore and stroll by the shimmering waters during your South Portland vacation. If you're in need of some time out, a trip to South Portland is just what the doctor ordered. We have plenty of South Portland vacation deals to choose from. Book one close to Willard Beach, just 2 kilometres from the downtown area, and live out your vacation dreams without blowing your budget.

Things You Should Know About South Portland

  • Spend your escape by the water and let the stresses of daily life drift away with the ocean breeze. Check out our South Portland beach hotels and indulge in a little beachside bliss.
  • South Portland also has a decent range of private vacation homes. Home2 Suites by Hilton Portland Airport and TownePlace Suites by Marriott Portland Airport ME are a hit with travellers and are worth taking a look at.
  • Roughly 23,900 people live in South Portland. If you'd like advice about things to see and do, why not ask one or two of the locals? Our South Portland things to do page is also a great source of info.
  • Don't leave town without checking out Maine Mall, Maine Mall and Willard Beach. With the money you save through our South Portland vacation deals, you can see more top attractions like these.

Ready to book your vacation to South Portland?

Choose your dates

South Portland Hotel Deals

Clarion Pointe South Portland

Clarion Pointe South Portland

675 Main Street I-95 South Portland ME
Fully refundable
CA $129
CA $141 total
Sep 13 - Sep 14
includes taxes & fees
Clarion Pointe South Portland
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

738 Main Street South Portland ME
Fully refundable
CA $133
CA $145 total
Sep 14 - Sep 15
includes taxes & fees
Quality Inn & Suites South Portland
Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

90 Maine Mall Rd South Portland ME
Fully refundable
CA $159
CA $174 total
Sep 7 - Sep 8
includes taxes & fees
Comfort Inn South Portland Airport
See all 2,781 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.

Stay near popular South Portland attractions

A lighthouse at sunset by the water.

Bug Light

9.0/10 (344 reviews)
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.
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A lighthouse, a pier, and people walking along the shore.

Fort Preble

8.8/10 (129 reviews)
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.
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A golden mask with red and gold decorations, a red rose, and sheet music.

Lyric Music Theater

7.4/10 (61 reviews)
You can enjoy a show at Lyric Music Theater during your trip to South Portland. Experience the area's entertainment choices or attend a sporting event.
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Maine Mall

8.4/10 (1,708 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.
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Willard Beach

8.2/10 (161 reviews)
Why not spend a carefree afternoon at Willard Beach during your travels in South Portland?
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South Portland Historical Society Museum

8.0/10 (84 reviews)
You can spend an afternoon exploring the galleries in South Portland Historical Society Museum during your travels in South Portland. Experience the area's great live music and entertainment choices.
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Maine Military Museum

7.8/10 (83 reviews)
You can spend an afternoon exploring the galleries in Maine Military Museum during your travels in South Portland. Experience the area's entertainment choices and great live music.
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What to do in South Portland

Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

CA $109
per adult
90% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Morning Lighthouse Cruise Along the Coast of Portland Maine

Morning Lighthouse Cruise Along the Coast of Portland Maine

CA $83
per adult
Morning Lighthouse Cruise Along the Coast of Portland Maine
See all activities in South Portland

Frequently asked questions

How much does a South Portland vacation package cost?
You can snap up a vacation package to this destination from CA $1,366 on Expedia. But how much your vacation to South Portland costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to South Portland?
You're likely to find reduced prices and greater availability in January, February and November. Browse our cheap South Portland vacation packages and you could get some great off-season discounts.
How many days is enough for South Portland?
South Portland vacations come in many shapes and sizes, but to get a real feel for this place, we'd suggest 2 days is about right. In this timeframe, you can fit in top sights like Higgins Beach and State Theatre along with hidden gems. Don't miss out on neighbourhoods such as Downtown Portland and Old Port either. If you're smart with your time, you can even take a day trip or two from South Portland too.
Is it worth booking a vacation package to South Portland?
South Portland has everything you need for an unforgettable getaway. Get your South Portland vacation off to a flying start by checking out popular attractions like Willard Beach.
How to find the best South Portland package deals?
Use Expedia's handy filters to find some terrific South Portland package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for South Portland package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a South Portland vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and stays individually. Better still, you can customize your South Portland getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to South Portland?
If you're planning a spontaneous South Portland getaway, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your flights and hotels by booking ahead.
How to plan a trip to South Portland?
  1. Pick your travel dates: What you plan to do in South Portland and your preferred season will help you decide when to get away.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and dining out to activities and flights. Your hotel will likely be the biggest expense during your trip to South Portland.
  3. Set the duration of your trip: Start by compiling a list of the activities and sights you want to get to in South Portland. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalized South Portland vacation package.

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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.