Book Exclusive South Portland Vacation Packages

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South Portland flight + hotel packages

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
May 24 - May 27
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Stay at this 5-star luxury hotel in Boston. Enjoy free WiFi, 2 restaurants, and a full-service spa. Popular attractions Copley Square and Boston Common are located nearby. Discover genuine guest reviews for Raffles Boston, in Back Bay neighborhood, along with the latest prices and availability – book now.
The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
per person
Jun. 4 - Jun. 10
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Stay at this business-friendly hotel in Boston. Enjoy free breakfast, free WiFi, and onsite parking. Popular attractions Fenway Park and Harvard Square are located nearby. Discover genuine guest reviews for The Boston Hotel, in Brighton neighborhood, along with the latest prices and availability – book now.
Hampton Inn Boston - Logan Airport

Hampton Inn Boston - Logan Airport

3 out of 5
per person
Jun. 28 - Jul. 2
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
Stay at this 3-star business-friendly hotel in Revere. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Encore Boston Harbor and Boston Harbor are located nearby. Discover genuine guest reviews for Hampton Inn Boston - Logan Airport along with the latest prices and availability – book now.
Doubletree By Hilton Boston Logan Airport Chelsea

Doubletree By Hilton Boston Logan Airport Chelsea

4 out of 5
per person
Jun. 28 - Jul. 2
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
Stay at this 4-star hotel in Chelsea. Enjoy free WiFi, breakfast, and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby. Discover genuine guest reviews for Doubletree By Hilton Boston Logan Airport Chelsea along with the latest prices and availability – book now.
The Dagny Boston

The Dagny Boston

4 out of 5
Downtown Boston
per person
May 23 - May 27
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
Stay at this 4-star historic hotel in Boston. Enjoy free WiFi, breakfast, and room service. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby. Discover genuine guest reviews for The Dagny Boston, in Downtown Boston neighborhood, along with the latest prices and availability – book now.
Prices and availability subject to change. Additional terms may apply.

Top South Portland hotels deals

Casco Bay Hotel, Ascend Hotel Collection

Casco Bay Hotel, Ascend Hotel Collection

3.5 out of 5
80 John Roberts Rd., South Portland, ME
Free cancellation
Reserve now, pay when you stay
The price is CA $110 per night
CA $110
per night
Apr. 21 - Apr. 22
Stay at this 3.5-star business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maine Mall and Thompson's Point are located nearby. Discover genuine guest reviews for Casco Bay Hotel, Ascend Hotel Collection along with the latest prices and availability – book now.
Comfort Inn Airport

Comfort Inn Airport

2.5 out of 5
90 Maine Mall Rd, South Portland, ME
Free cancellation
Reserve now, pay when you stay
The price is CA $105 per night
CA $105
per night
Apr. 21 - Apr. 22
Stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the clean rooms in our reviews. Popular attractions Maine Mall and Thompson's Point are located nearby. Discover genuine guest reviews for Comfort Inn Airport along with the latest prices and availability – book now.
Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

2.5 out of 5
369 Maine Mall Road, South Portland, ME
Free cancellation
Reserve now, pay when you stay
The price is CA $142 per night
CA $142
per night
Apr. 28 - Apr. 29
Stay at this hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Maine Mall and Thompson's Point are located nearby. Discover genuine guest reviews for Tru by Hilton Portland Airport Area along with the latest prices and availability – book now.
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
363 Maine Mall Rd, South Portland, ME
Free cancellation
Reserve now, pay when you stay
The price is CA $151 per night
CA $151
per night
Apr. 24 - Apr. 25
Stay at this hotel in South Portland. Enjoy free WiFi, free parking, and breakfast. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maine Mall and Thompson's Point are located nearby. Discover genuine guest reviews for DoubleTree by Hilton Hotel Portland along with the latest prices and availability – book now.
Quality Inn & Suites

Quality Inn & Suites

2.5 out of 5
738 Main Street, South Portland, ME
Free cancellation
Reserve now, pay when you stay
The price is CA $116 per night
CA $116
per night
Apr. 22 - Apr. 23
Stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Thompson's Point are located nearby. Discover genuine guest reviews for Quality Inn & Suites along with the latest prices and availability – book now.
Hampton Inn Portland Airport

Hampton Inn Portland Airport

2.5 out of 5
171 Philbrook Ave, South Portland, ME
Free cancellation
Reserve now, pay when you stay
The price is CA $118 per night
CA $118
per night
Apr. 25 - Apr. 26
Stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Maine Mall and Thompson's Point are located nearby. Discover genuine guest reviews for Hampton Inn Portland Airport along with the latest prices and availability – book now.
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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.

Popular places to visit

Image for Bug Light

Bug Light

You can find out about the history of South Portland with a visit to Bug Light. Experience the area's acclaimed theater scene and entertainment choices.

Bug Light
Image for Fort Preble

Fort Preble

Find out about the history of South Portland when you take a trip to Fort Preble. Experience the area's acclaimed theater scene and entertainment choices.

Fort Preble
Image for Maine Mall

Maine Mall

4/5(64 reviews)

You can do some window-shopping at Maine Mall during your visit to South Portland. Experience the area's great live music and entertainment choices.

Maine Mall

South Portland Vacations

Unwittingly stumbling upon a new place is what makes traveling so great, But of course, it never hurts to understand a little about the area before you pack your bags. We'll get you up to speed on a few basics about South Portland.

About 2 miles (3 kilometers) to the southwest of the heart of Portland, South Portland is one of the neighborhoods that make this city so inviting.

Portland is home to some 66,000 locals.

Places to visit in South Portland

University of Southern Maine has long been a hotbed for progressive ideas, game-changing research and leaders of the future. See if you can traipse through its historic halls and mingle with students on a guided tour. Want some more nearby options? Adore all things art? Treat your eyes to interesting works and try to interpret the story behind them at Portland Museum of Art. But that's not all. Nothing gives us a glimpse into bygone days quite like historic buildings. Why not tour the inside of Victoria Mansion and find out what went on under its roof?

Where do you fly into for South Portland?

Airfares booked for Portland International Jetport Airport (PWM)? Walk through the security gates, head out of the terminal and you'll be 2 miles (3 kilometers) to the northwest from the heart of South Portland.

Frequently asked questions

How much are vacation packages to South Portland?
Packages, which include flights and hotels in South Portland, start from as low as CA $950. Make your travel fantasies come to life and secure your dream vacation with Travelocity today.
Where can I get the best vacation package deals for South Portland?
There’s no need to look any further than Travelocity. With no less than 400 air carriers and 665,000 properties across the globe, it’s a piece of cake to find a South Portland package deal that satisfies your wanderlust.
Why should I purchase my South Portland vacation package with Travelocity?
We’ve got 24/7 customer support, excellent service and a Price Match Guarantee. Life’s a great big journey — and we have alluring destinations for you to journey to all over the world. Wander with us and your bank balance will thank you for it.
Can I save on my South Portland car rental if I combine it with my hotel or flight?
Definitely — and if you also add an experience or activity to your South Portland vacation package, you’ll pick up even greater savings. With a package, you can find things to do in the area that are right up your alley. Then, hop in your rental car and work your way through the list. Fenway Park is one must-see attraction to put on your itinerary. It’s 159 kilometersfrom South Portland.
What is the best time of year to go to South Portland?
Traveling in the off-season, , comes with a bevy of benefits — think cheaper flights and hotels and less pushing past masses of tourists. But there’s a real charm to the destination during the high season. More events are likely to be on and more attractions will be open in . If you want to stretch your budget, offers the lowest hotel prices. You’ll pay a lot more for a bed in .
What is there to do in South Portland?
Grab your travel schedule and make a note of Maine Mall and Willard Beach. They are two of the most popular sights in South Portland.
Where should I stay when visiting South Portland?
If you’re looking to get the most out of your budget, consider the Days Inn by Wyndham Airport/Maine Mall (2.0 stars) and the Howard Johnson Hotel by Wyndham South Portland (2.0 stars). With all that extra cash, stay a while longer in South Portland and make even more wonderful memories.
Can I go on vacation to South Portland at this time?
Discover all the info that’s important relating to travel restrictions and quarantine policies ahead of your journey to South Portland. Our Covid-19 Travel Advisor is full of advice to help make your vacation relaxed and stress-free.