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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,008, price is now CA $536 per person
CA $536
per person
Nov 1 - Nov 3
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $3,757, price is now CA $2,165 per person
CA $2,165
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
The Reffles Hotel is a fabulous place to stay. Hotel is amazing with a wonderful friendly staff.

Reviewed on Aug. 20, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,269, price is now CA $2,097 per person
CA $2,097
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
The staff were amazing, rooms were spotless and with wonderful amenities and special touches.

Reviewed on Aug. 22, 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Price was CA $2,161, price is now CA $1,430 per person
CA $1,430
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (1,108 reviews)
Heather was unbelievable in every way. Because of her past excellent service we returned!! She makes this hotel experience a true pleasure. Thank you Heather for your kind and gracious assistance.

Reviewed on Aug. 21, 2025

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Price was CA $1,455, price is now CA $967 per person
CA $967
per person
Nov 2 - Nov 6
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,002 reviews)
Great Experience at a great location

Reviewed on Aug. 21, 2025

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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Knightville

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

Find hotels in Knightville

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

Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Aug 24 to Aug 25
CA $161
CA $176 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,214 reviews)
"."

Reviewed on Aug. 21, 2025

Days Inn by Wyndham Airport/Maine Mall
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
The price is CA $124 per night from Sep 21 to Sep 22
CA $124
CA $135 total
Sep 21 - Sep 22
includes taxes & fees
7.4/10 Good! (159 reviews)
"Great price, clean and comfortable."

Reviewed on Aug. 19, 2025

Germaine Inn South Portland
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 $186 per night from Aug 26 to Aug 27
CA $186
CA $203 total
Aug 26 - Aug 27
includes taxes & fees
8.4/10 Very Good! (1,497 reviews)
"Good"

Reviewed on Aug. 20, 2025

Comfort Inn Airport
See all 2,713 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
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Discover the most popular places to visit in South Portland

Maine Mall

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

Seven Portland Lighthouses Tour

Seven Portland Lighthouses Tour

CA $136
per adult
Seven Portland Lighthouses Tour
Portland Head Light

Portland Bicycle Tour with 5 Lighthouse Stops and XL Lobster Roll

CA $227
per adult
100% of travellers recommend
Portland Bicycle Tour with 5 Lighthouse Stops and XL Lobster Roll
Lighthouse to Lagers Tour with Craft Beer

Lighthouse to Lagers Tour with Craft Beer

CA $118
per adult
Lighthouse to Lagers Tour with Craft Beer
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 $536 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.

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