South Portland Holidays

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Top Flight + Hotel Deals in South Portland

Price found within the past 48 hours. Click for updated prices.
The Boxer

The Boxer

4 out of 5
West End
per person
18 Jan - 23 Jan
found 11 hours ago
Return flight included
Shannon (SNN) to Boston (BOS)
8.6/10 Excellent! (1,023 reviews)
Front desk in the evening could be nicer.

Reviewed on 25 Nov 2024

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
18 Jan - 23 Jan
found 11 hours ago
Return flight included
Shannon (SNN) to Boston (BOS)
9.6/10 Exceptional! (64 reviews)
Excellent hotel. The only thing was that the AC in our room was so loud when turned on that it was unbearable. The hotel did help us move to another room that did not have the problem. We were only there for a night. We will definitely stay again as it is an excellent hotel otherwise.

Reviewed on 27 Oct 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
18 Jan - 23 Jan
found 11 hours ago
Return flight included
Shannon (SNN) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Super place, great service

Reviewed on 6 Nov 2024

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
18 Jan - 23 Jan
found 11 hours ago
Return flight included
Shannon (SNN) to Boston (BOS)
9.2/10 Wonderful! (316 reviews)
Awesome place to stay if you’re wanting to do a lot of things downtown.

Reviewed on 25 Nov 2024

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
18 Jan - 23 Jan
found 11 hours ago
Return flight included
Shannon (SNN) to Boston (BOS)
9.6/10 Exceptional! (323 reviews)
I loved the hotel: it is new, everything is so nice and beautiful!!!

Reviewed on 12 Nov 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

Willard might not have many top sights, but Willard Beach and Victoria Mansion are two attractions nearby that you can check out.

Find hotels in Willard

South Portland Beach Holiday

Live out those beachy daydreams on your South Portland holiday. 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 centre, Willard Beach is the place to be for many sun-seeking visitors. Look through our South Portland holiday deals and watch your travel budget stretch further!

Top hotels in South Portland

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 €74 per night from 10 Dec to 11 Dec
€74
includes taxes & fees
10 Dec - 11 Dec
8.4/10 Very Good! (2,379 reviews)
"Stellar"

Reviewed on 23 Nov 2024

Casco Bay Hotel, Ascend Hotel Collection
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 €79 per night from 10 Dec to 11 Dec
€79
includes taxes & fees
10 Dec - 11 Dec
7.8/10 Good! (1,034 reviews)
"Clean, friendly, free parking"

Reviewed on 24 Nov 2024

DoubleTree by Hilton Hotel 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 €66 per night from 10 Dec to 11 Dec
€66
includes taxes & fees
10 Dec - 11 Dec
8.2/10 Very Good! (1,024 reviews)
"NA"

Reviewed on 23 Nov 2024

Comfort Inn Airport
See all 2,400 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 holiday package cost?
The cheapest South Portland holiday package is €751, 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 holiday package. It’s that easy! From flights and hotels to rental cars and activities, Expedia makes travelling 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 neighbourhood, 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 holiday?
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 holiday 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 holiday 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 holiday package is the easiest way to organise 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 holiday package?
With a holiday 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 holiday 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 holiday 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.

Popular places to visit

Maine Military Museum

You can enjoy some culture when you stop by Maine Military Museum in South Portland. Experience the area's entertainment choices or attend a sporting event.

Maine Military Museum

What to do in South Portland

Half Day Private Boat Charter from Portland

Half Day Private Boat Charter from Portland

€606
Per adult
Half Day Private Boat Charter from Portland
Portland Downtown Highlights: "The Golden Adventure" Exploration Game

Downtown Golden Adventure Quest Experience in Portland

€10
Per adult
Downtown Golden Adventure Quest Experience in Portland
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

€9
Per adult
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
See all activities in South Portland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.