South Portland Holidays

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South Portland Flight & Hotel Packages

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

The Revolution Hotel

3.5 out of 5
South End
Price was S$1,861, price is now S$1,358 per person
S$1,358
per person
10 May - 15 May
found 1 day ago
Return flight included
Toronto (YYZ) to Boston (BOS)
9/10 Wonderful! (2,535 reviews)
We had a room with the bathroom inside. Nice size room, but no where for luggage or clothes. Close to a few spots to eat, train stop in walking distance about 15 minutes.

Reviewed on 27 Mar, 2026

Hotel AKA Boston Common

Hotel AKA Boston Common

4 out of 5
Downtown Boston
Save 100% on your flight
Price was S$5,745, price is now S$3,663 per person
S$3,663
per person
10 May - 15 May
found 1 day ago
Return flight included
Toronto (YYZ) to Boston (BOS)
9/10 Wonderful! (1,522 reviews)
Amazing staff, room had great city view (beautiful at night). Very comfortable, very clean. Gym was fine for a couple days and they have an Equinox partnership if you need more machines.

Reviewed on 27 Mar, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was S$2,160, price is now S$1,440 per person
S$1,440
per person
10 May - 15 May
found 1 day ago
Return flight included
Toronto (YYZ) to Boston (BOS)
8.6/10 Excellent! (1,395 reviews)
The room we stayed in was very very dark, very little natural light and lighting in the room was not fully functional. Room was also right on top and I mean right on top of the elevator, so pretty steady stream of noise into our room from there.

Reviewed on 27 Mar, 2026

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was S$2,364, price is now S$1,700 per person
S$1,700
per person
10 May - 15 May
found 1 day ago
Return flight included
Toronto (YYZ) to Boston (BOS)
9/10 Wonderful! (2,995 reviews)
Quiet and comfortable room in a great location. Room was smaller but cleanliness, service, and value were excellent.

Reviewed on 24 Mar, 2026

Cambridge Common House

Cambridge Common House

3.5 out of 5
West Cambridge
Price was S$1,873, price is now S$1,384 per person
S$1,384
per person
10 May - 15 May
found 1 day ago
Return flight included
Toronto (YYZ) to Boston (BOS)
No reviews

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
Bug Light

Willard Beach

2 out of top 10 points of interest in this area

When in Willard Beach, you can plan a visit to Willard Beach and Portland Harbor Museum, some noteworthy sights in the nearby area.

Find hotels in Willard Beach

South Portland Beach Holiday

Listen to the soothing sound of waves rolling into the shore and stroll by the shimmering waters during your South Portland holiday. 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 holiday deals to choose from. Book one close to Willard Beach, just 2 kilometres from the downtown area, and live out your holiday 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 holiday 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 holiday deals, you can see more top attractions like these.

Top hotels in South Portland

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 S$114 per night from 3 Apr to 4 Apr
S$114
3 Apr - 4 Apr
includes taxes & fees
8/10 Very Good! (1,369 reviews)
Pool was nice. Very convenient to shopping, restaurants & activities. Great price for what you get.

Reviewed on 27 Mar, 2026

DoubleTree by Hilton Hotel Portland
Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

3 out of 5
369 Maine Mall Road South Portland ME
Fully refundableReserve now, pay when you stay
The price is S$114 per night from 7 Apr to 8 Apr
S$114
7 Apr - 8 Apr
includes taxes & fees
8.8/10 Excellent! (1,763 reviews)
We enjoyed our one night stay! Clean, comfy, good breakfast & we were so happy to receive a welcome gift bag with bottled waters & popcorn. Will definitely stay again & try out the pool they share wirh Double Tree next door!

Reviewed on 27 Mar, 2026

Tru by Hilton Portland Airport Area
Spark by Hilton Portland Airport Maine Mall

Spark by Hilton Portland Airport Maine Mall

2 out of 5
461 Maine Mall Rd South Portland ME
Fully refundableReserve now, pay when you stay
The price is S$85 per night from 16 Apr to 17 Apr
S$85
16 Apr - 17 Apr
includes taxes & fees
7.8/10 Good! (1,421 reviews)
There was no hot tub

Reviewed on 26 Mar, 2026

Spark by Hilton Portland Airport Maine Mall
See all 2,669 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 Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

S$22
per traveller
Portland Smartphone Audio Tour: Self-Guided Drive
Maine: Portland Smartphone-Based Walking Audio Tour

Maine: Portland Smartphone-Based Walking Audio Tour

S$16
per traveller
Maine: Portland Smartphone-Based Walking Audio Tour
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

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

S$13
per traveller
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
See all activities in South Portland

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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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.