A lighthouse, rocky coastline, and a sunset over the ocean.

South Portland Vacation Packages

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Your South Portland Vacation

With one of our vacation packages to South Portland, you'll discover infinite opportunities for fun and relaxation. There's so much to enjoy, including its coastal scenery and lively atmosphere. If your trip to South Portland includes a little sightseeing, drop by much-loved attractions like Portland Head Light, University of Southern Maine and Portland Museum of Art. A couple of quick clicks is all it takes to put together a tailored South Portland vacation on Expedia.

Top South Portland vacation deals

Price found within the past 48 hours. Click for updated prices.
  • A spacious hotel lobby with a dining area, seating, large windows, and a chandelier.
    Jan 29 - Jan 31

    Boston Harbor Hotel + Flight

    North End
    2 nights
    5.0 star property
    9.8/10 - Exceptional (1,006 reviews)
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YTZ - BOS • 1 stop BOS - YTZ • Nonstop
    CA $1,530
    CA $963
    per traveller
    found 1 day ago
    Boston Harbor Hotel
  • A brick building with arched windows and a black door, surrounded by greenery and a metal fence.
    Jan 29 - Feb 1

    Four Seasons Hotel Boston + Flight

    Bay Village
    3 nights
    5.0 star property
    9.4/10 - Exceptional (497 reviews)
    "The best location and the beat service! The best swimming pool"
    Reviewed November 9, 2026
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YTZ - BOS • 1 stop BOS - YYZ • Nonstop
    CA $2,397
    CA $1,548
    per traveller
    found 1 day ago
    Four Seasons Hotel Boston
  • Pool
    Jan 14 - Jan 17

    Raffles Boston + Flight

    Back Bay
    3 nights
    5.0 star property
    9.6/10 - Exceptional (354 reviews)
    "Amazing hotel Great rooms and helpful, professional staff. Couldn’t fault it."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YTZ - BOS • 1 stop BOS - YTZ • Nonstop
    Save 100% on your flight
    CA $2,235
    CA $1,488
    per traveller
    found 1 day ago
    Raffles Boston
  • A park with a lamp post, a bridge, and buildings in the background.
    Jan 14 - Jan 17

    The Newbury Boston + Flight

    Back Bay
    3 nights
    5.0 star property
    9.4/10 - Exceptional (747 reviews)
    "Beautiful hotel and the staff was wonderful. They gave us a corner room with a great view of the city. The room was spacious with a comfortable seating area."
    Reviewed November 7, 2026
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YTZ - BOS • 1 stop BOS - YTZ • Nonstop
    Save 100% on your flight
    CA $1,789
    CA $1,298
    per traveller
    found 1 day ago
    The Newbury Boston
  • A large hotel with a curved facade and the name "Encore" illuminated on the top.
    Dec 10 - Dec 13

    Encore Boston Harbor + Flight

    Everett
    3 nights
    5.0 star property
    9.6/10 - Exceptional (4,347 reviews)
    Roundtrip • Toronto (YTO) - Boston (BOS)
    YKF - BOS • 1 stop BOS - YKF • 1 stop
    CA $1,566
    CA $1,179
    per traveller
    found 1 day ago
    Encore Boston Harbor

Where to stay in South Portland

Find the best South Portland areas and neighborhoods for the activities you enjoy most.
A coastal cityscape with a marina, buildings, and a clear blue sky.

Knightville

Knightville offers a slice of authentic Maine living just across the bridge from Portland. This quiet area blends waterfront charm with small-town character. Stroll along the Eastern Waterfront Trail for stunning views of Portland's skyline across the Fore River. Bug Light Park's historic lighthouse stands as the area's maritime centrepiece. Tree-lined streets showcase classic New England architecture with white clapboard houses and colourful shutters. Local eateries serve fresh Maine seafood at prices lower than neighbouring Portland. The peaceful residential setting provides a perfect retreat after exploring nearby attractions like Victoria Mansion and Portland Museum of Art.
A lighthouse on a rocky breakwater, a large building across the water, and a clear sky.

Willard Beach

This charming coastal gem offers a peaceful retreat with a beautiful sandy shoreline. Willard Beach in South Portland welcomes visitors with gentle waves and a cozy area vibe. The small beach area attracts locals and tourists looking for a quieter Maine coastal experience. Green spaces like Willard Beach Park provide perfect spots for picnics and relaxation. Weathered New England-style homes with classic coastal architecture line quiet residential streets. Nearby attractions include Bug Light and Southern Maine Community College, making this an ideal base for exploring Portland's waterfront treasures.

Highland

Though Highland might not have many top sights, you can venture to the surrounding area to see attractions like Thompson's Point and Maine Mall.
Two people sitting on a red bench outside a bakery with a sign that reads "Scratch Baking Co."
Photo by Karen Rinaldo-green
Open Photo by Karen Rinaldo-green

Willard

Willard Beach offers a peaceful coastal retreat in South Portland where the sandy shoreline meets Casco Bay's island-dotted waters. This charming New England area features weathered rocks and gentle waves perfect for those seeking ocean views. Fort Gorges sits majestically offshore while Willard Square provides a cozy community gathering spot. The neighborhood's white clapboard houses and cedar-shingled homes create an authentic Maine coastal atmosphere away from tourist crowds. Enjoy swimming in calm waters, explore fascinating tide pools, or stroll along scenic shoreline paths. With minimal commercialization and quiet residential streets, Willard delivers a genuine local experience just minutes from Portland.
A lighthouse, sailboats, and a cityscape with buildings and trees along the waterfront.

Meetinghouse Hill

Discover the historic charm of Meetinghouse Hill, where 19th-century architecture lines quiet, tree-shaded streets in South Portland. This peaceful residential haven offers glimpses of Casco Bay through mature oak and maple canopies. Walking tours reveal well-preserved colonial and Victorian homes with classic New England character. The area provides an authentic slice of coastal Maine living away from tourist crowds. Nearby attractions include Willard Beach, Victoria Mansion, and Portland Museum of Art. Though dining options are sparse within the area, charming bed & breakfasts in converted historic homes offer intimate, personalized stays.

Discover the most popular places to visit in South Portland

A lighthouse at sunset by the water.

Bug Light

9.0/10 (344 reviews)
You can find out about the history of South Portland with a visit to Bug Light. Experience the area's acclaimed theater scene and great live music.
See properties

What to do in South Portland

Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

CA $24
per traveller
100% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
See all activities in South Portland

South Portland Hotel Deals

A hotel room with a bed, a TV, a desk, and a view of a lighthouse through a mural.

Clarion Pointe South Portland

Clarion Pointe South Portland
2.0 star property
5.8 km from South Portland
7.2 out of 10, Good, (1,052 reviews)
"Hôtel très bien situé, près de tous les services. Personnel courtois et attentionné, chambre très propre et tranquille."
The price is CA $72
CA $79 total
includes taxes & fees
Dec 8 - Dec 9
Clarion Pointe 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.
See all properties in South Portland

Frequently Asked Questions

How much does a South Portland vacation package cost?

You can snap up a vacation package to this destination from CA $963 on Expedia. But how much your vacation to South Portland costs will depend on the season, length of stay and hotel choice.

What are the cheapest months to go to South Portland?

You're likely to find reduced prices and greater availability in January, February and November. Browse our cheap South Portland vacation packages and you could get some great off-season discounts.

How many days is enough for South Portland?

South Portland vacations come in many shapes and sizes, but to get a real feel for this place, we'd suggest 2 days is about right. In this timeframe, you can fit in top sights like Higgins Beach and State Theatre along with hidden gems. Don't miss out on neighbourhoods such as Downtown Portland and Old Port either. If you're smart with your time, you can even take a day trip or two from South Portland too.

Is it worth booking a vacation package to South Portland?

South Portland has everything you need for an unforgettable getaway. Get your South Portland vacation off to a flying start by checking out popular attractions like Willard Beach.

How to find the best South Portland package deals?

Use Expedia's handy filters to find some terrific South Portland package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for South Portland package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.

Is it cheaper to book a South Portland vacation as a package?

An Expedia vacation package could score you significant savings when compared to booking flights and stays individually. Better still, you can customize your South Portland getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.

When to book a vacation package to South Portland?

If you're planning a spontaneous South Portland getaway, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your flights and hotels by booking ahead.

How to plan a trip to South Portland?

  1. Pick your travel dates: What you plan to do in South Portland and your preferred season will help you decide when to get away.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and dining out to activities and flights. Your hotel will likely be the biggest expense during your trip to South Portland.
  3. Set the duration of your trip: Start by compiling a list of the activities and sights you want to get to in South Portland. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights 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.