South Portland Vacations from ￥86,511

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The Latest South Portland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
Bay Village
Save 100% on your flight
per person
Aug 27 - Aug 29
found 12 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
8.4/10 Very Good! (3,336 reviews)
Very good location.

Reviewed on Jun 5, 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 27 - Aug 29
found 12 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
Always a great stay. Property is getting a little bit dated and could use a refresh. The house keeping staff is the best!

Reviewed on Jun 3, 2024

The Boxer

The Boxer

4 out of 5
West End
per person
Aug 27 - Aug 29
found 12 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
8.6/10 Excellent! (1,006 reviews)
It was a good hotel

Reviewed on Jun 4, 2024

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
per person
Aug 27 - Aug 29
found 12 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (283 reviews)
This was one of the best hotel experiences I've had. The staff goes above and beyond to make you feel welcomed. From the Tates cookies and sparkling water available, to the water bottles at the end of the night, they really pay attention to small details, making it a great experience. The rooms were clean and roomy. We ended up walking the entire time in Boston since the hotel was at a great location, but if you plan on driving, keep in mind that you have to call ahead of time to access your car. Would definitely stay again!

Reviewed on May 28, 2024

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
per person
Aug 27 - Aug 29
found 12 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (2,257 reviews)
Beautiful top of the line high class reality and casino. Amazing rooms and amenities. This is not a basic hotel by any means so expect to pay much more for the accommodations.

Reviewed on Jun 5, 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 hotels 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 kilometers 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

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 ￥12,405 per night from Jun 6 to Jun 7
￥12,405
per night
Jun 6 - Jun 7
7.6/10 Good! (1,019 reviews)
"The staff was very helpful with setting up the free shuttle to the airport."

Reviewed on Jun 4, 2024

Days Inn by Wyndham Airport/Maine Mall
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 ￥17,034 per night from Jun 9 to Jun 10
￥17,034
per night
Jun 9 - Jun 10
8.4/10 Very Good! (1,538 reviews)
"The room was gigantic and nice. The lobby was very pretty. My only complaint is the outside is not very inviting but not much can be done about that. The room was really great and had pick up/ drop off to airport"

Reviewed on Jun 3, 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 ￥13,937 per night from Jun 9 to Jun 10
￥13,937
per night
Jun 9 - Jun 10
8.2/10 Very Good! (1,011 reviews)
"Stay was good and all went well . I did forget my phone charger cord and plug in in my room . I would pick it up Tuesday late in the day if they have it ?"

Reviewed on Jun 2, 2024

Comfort Inn Airport
See all 2,425 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.

Frequently asked questions

How much does a South Portland vacation package cost?
The cheapest South Portland vacation package is ￥86,511, 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

Image for Bug Light

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 entertainment choices and acclaimed theater scene.

Bug Light
Image for Fort Preble

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
Image for Maine Mall

Maine Mall

4/5(607 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

￥95,752
Per adult
Half Day Private Boat Charter from Portland
Image for Portland: Old Port Seafood Lovers Tour

Portland: Old Port Seafood Lovers Tour

￥21,506
Per adult
Portland: Old Port Seafood Lovers Tour
Image for Portland, Maine: Old Port Brewery & Pub Walking Tour

Portland, Maine: Old Port Brewery & Pub Walking Tour

￥13,111
Per adult
Portland, Maine: Old Port Brewery & Pub Walking Tour
See all activities in South Portland

Other vacations you might like

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