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

South Portland Holidays from AU$3,290

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The Latest South Portland holiday deals

Price found within the past 48 hours. Click for updated prices.
  • 2 Oct - 7 Oct

    Eurostars The Boxer + Flight

    West End
    5 nights
    4.0 star property
    8.8/10 - Excellent (1,528 reviews)
    "Not really sure what the amenities were but in a great location"
    Reviewed July 16, 2026
    Return Sydney (SYD) - Boston (BOS)
    SYD - BOS1 stop BOS - SYD2 stops
    AU$4,400
    AU$3,290
    per traveller
    found 19 hours ago
    Eurostars The Boxer
  • 2 Oct - 7 Oct

    The Godfrey Hotel Boston + Flight

    Downtown Boston
    5 nights
    4.0 star property
    9.6/10 - Exceptional (5,120 reviews)
    "So impressed with this hotel. Snacks and water were free in the rooms. The staff was super helpful - clean rooms. Bar within the the hotel as well as a cafe."
    Reviewed July 16, 2026
    Return Sydney (SYD) - Boston (BOS)
    SYD - BOS1 stop BOS - SYD2 stops
    AU$4,572
    AU$3,476
    per traveller
    found 19 hours ago
    The Godfrey Hotel Boston
  • 2 Oct - 7 Oct

    Good Hotels Boston + Flight

    South End
    5 nights
    2.0 star property
    8.0/10 - Very good (55 reviews)
    "This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order."
    Reviewed May 23, 2026
    Return Sydney (SYD) - Boston (BOS)
    SYD - BOS1 stop BOS - SYD2 stops
    AU$4,273
    AU$3,514
    per traveller
    found 19 hours ago
    Good Hotels Boston
  • 2 Oct - 7 Oct

    The Lenox Hotel Boston + Flight

    Back Bay
    5 nights
    4.5 star property
    9.6/10 - Exceptional (1,609 reviews)
    "Great location, nice hotel and lovely staff"
    Reviewed July 15, 2026
    Return Sydney (SYD) - Boston (BOS)
    SYD - BOS1 stop BOS - SYD2 stops
    AU$4,628
    AU$3,806
    per traveller
    found 19 hours ago
    The Lenox Hotel Boston
  • 2 Oct - 7 Oct

    Hotel AKA Back Bay + Flight

    Back Bay
    5 nights
    4.5 star property
    9.4/10 - Exceptional (1,296 reviews)
    Return Sydney (SYD) - Boston (BOS)
    SYD - BOS1 stop BOS - SYD2 stops
    AU$4,287
    AU$3,552
    per traveller
    found 19 hours ago
    Hotel AKA Back Bay

Our guide on where to stay in South Portland

Find the best South Portland areas for the activities you enjoy most. Learn more about South Portland
Learn more about South Portland

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 weatherboard 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.

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 cosy 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.

Ligonia

Ligonia might not have many top sights, but Thompson's Point and Hadlock Field are two attractions nearby that you can check out.

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 cosy community gathering spot. The neighborhood's white weatherboard 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.

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, personalised stays.

Discover the most popular places to visit in South Portland

What to do in South Portland

South Portland Hotel Deals

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?

You can pick up a holiday package to this popular destination from AU$3,290 on Expedia. However, how much your holiday to South Portland costs will depend on factors like the length of stay, hotel choice and season.

What are the cheapest months to go to South Portland?

If you're hoping to book a cheap South Portland holiday package, consider travelling in January, February and November. You'll usually find lower prices on hotels and flights during these quieter months — ideal for a budget-friendly getaway.

How many days is enough for South Portland?

Allow at least 2 days for your South Portland holiday to discover all that makes this place special. Wander around key neighbourhoods, including Downtown Portland and Old Port. Then make a beeline for top sights like South Portland Historical Society Museum and Maine Mall. With a well-organised itinerary, you'll be kept busy with room for some rest time too. Want to venture outside of South Portland? Consider squeezing in a day trip or two.

Is it worth booking a holiday package to South Portland?

It's no wonder a South Portland holiday is on the must-do list of many travellers. Popular attractions like Willard Beach are just the start of things to see and do here.

How to find the best South Portland package deals?

Bagging a cheap South Portland package deal is easy with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most pocket-friendly South Portland package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.

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

Expedia holiday packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored South Portland holiday by choosing your preferred accommodation type, airline and car class.

When to book a holiday package to South Portland?

Score incredible discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment South Portland holiday.

How to plan a trip to South Portland?

  1. Choose the best time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to go to South Portland.
  2. Set a budget: Factor in expenses like flights, food and transportation when calculating how much to put aside for your trip to South Portland. Then, pick a property that fits your budget, whether that's an economical stay or a more luxurious retreat.
  3. Decide how long to go away for: Now that you know more about South Portland, you can work out the ideal length of your holiday. Pull together a draft plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a personalised South Portland holiday package.

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