South Portland Vacations from ￥233,882

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The Latest South Portland Vacation Packages

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

Boston Harbor Hotel

5 out of 5
North End
per person
Oct 23 - Oct 26
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
The Boston Harbor Hotel continues to be my absolute favorite place to stay in Boston, and my recent visit reminded me exactly why. From the moment I walked through the doors, I was greeted by the same welcoming and professional staff that makes this property truly special. The team went above and beyond by upgrading me to a suite, which was an unexpected and much-appreciated gesture that really enhanced my stay. The suite itself was beautifully appointed and comfortable, providing the perfect retreat after busy days exploring the city. What really sets this hotel apart is its unbeatable location. You simply cannot find a better spot in Boston - it's perfectly positioned for both business and leisure activities, with easy access to everything the city has to offer while maintaining that sense of waterfront tranquility. Every stay here has been delightful, and the consistency in service quality is remarkable. The Boston Harbor Hotel has earned my loyalty through their attention to detail and genuine hospitality. I'm already looking forward to my next visit!

Reviewed on Aug 11, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
Very convenient boutique hotel

Reviewed on Aug 5, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (433 reviews)
Great small boutique hotel. European feel and service. Lovely small garden in back. Good food.

Reviewed on Aug 11, 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8/10 Very Good! (571 reviews)
I had the best sleep! This property was quiet, elegant, and perfectly met my needs. I was in for business and often hotels are so loud and crowded. This property was so quiet and I could not hear any street noise. When you travel, sleep can be hard to find. This was truly and oasis. Everything was clean and there were lots of amenities. Very close to the subway, food, and shopping. Will recommend.

Reviewed on Aug 14, 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
per person
Oct 23 - Oct 26
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.8/10 Excellent! (235 reviews)
We enjoyed having the bistro on site.

Reviewed on Jul 17, 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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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.

Find hotels in Willard Beach

Find the Best South Portland Vacation Packages

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 kilometers 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 travelers 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.

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 ￥17,159 per night from Aug 24 to Aug 25
￥17,159
￥18,703 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,165 reviews)
"Very pleasantly surprised at this hotel. Ideally situated, clean and staff were excellent 🙏"

Reviewed on Aug 13, 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 ￥14,366 per night from Aug 24 to Aug 25
￥14,366
￥15,659 total
Aug 24 - Aug 25
includes taxes & fees
7.6/10 Good! (140 reviews)
"No comment"

Reviewed on Aug 13, 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 ￥19,286 per night from Sep 14 to Sep 15
￥19,286
￥21,022 total
Sep 14 - Sep 15
includes taxes & fees
8.4/10 Very Good! (1,478 reviews)
"The bed was quite comfortable and the breakfast options were good. The morning staff was great. My only complaint was that I had reserved an accessible room with a queen bed but they didnt save one for me. Other than that, the place was ok"

Reviewed on Aug 12, 2025

Comfort Inn Airport
See all 2,745 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.

What to do in South Portland

Portland Head Light

Portland Bicycle Tour with 5 Lighthouse Stops and XL Lobster Roll

￥23,483
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

￥12,701
per adult
Lighthouse to Lagers Tour with Craft Beer
Maine Coastal Lighthouse:Two-hour bicycle tour

Maine Coastal Lighthouse:Two-hour bicycle tour

￥11,077
per adult
Maine Coastal Lighthouse:Two-hour bicycle tour
See all activities in South Portland

Frequently asked questions

How much does a South Portland vacation package cost?
You can pick up a vacation package to this popular destination from ￥233,882 on Expedia. However, how much your vacation to South Portland costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to South Portland?
If you're hoping to book a cheap South Portland vacation package, consider traveling in January, February and November. You'll usually find lower prices on hotels and flights during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for South Portland?
Allow at least 2 days for your South Portland vacation to discover all that makes this place special. Wander around key neighborhoods, including Downtown Portland and Old Port. Then make a beeline for top sights like South Portland Historical Society Museum and Maine Mall. With a well-organized itinerary, you'll be kept busy with room for some rest time too. Want to venture outside of South Portland? Consider squeezing in a day trip or two.
Is it worth booking a vacation package to South Portland?
It's no wonder a South Portland vacation is on the must-do list of many travelers. Popular attractions like Willard Beach are just the start of things to see and do here.
How to find the best South Portland package deals?
Bagging a cheap South Portland package deal is easy with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most pocket-friendly South Portland package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a South Portland vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored South Portland vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to South Portland?
Score incredible discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment South Portland vacation.
How to plan a trip to South Portland?

  1. Choose the best time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to go to South Portland.
  2. Set a budget: Factor in expenses like flights, food and transportation when calculating how much to put aside for your trip to South Portland. Then, pick a property that fits your budget, whether that's an economical stay or a more luxurious retreat.
  3. Decide how long to go away for: Now that you know more about South Portland, you can work out the ideal length of your vacation. Pull together a draft plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental 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.