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.
Boston Harbor Hotel
North End
CA $1,310
per person
Dec 10 - Dec 13
found 22 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
Everyone from outside arrival and beyond were helpful,
friendly and welcoming.
Reviewed on Oct 22, 2026
Four Seasons Hotel Boston
Bay Village
CA $1,640
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (487 reviews)
For the most high end hotel in Boston, lacked updated amenities that other newer hotels have. Rooms were severely dated.
Reviewed on Oct 20, 2026
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
Willard Beach
2 out of top 10 points of interest in this area
If you're looking for some top things to see and do in Willard Beach and surrounding area, you can visit Willard Beach and Spring Point Ledge Lighthouse.
Ferry Village
1 out of top 10 points of interest in this area
While there might not be top attractions in Ferry Village, you can explore the larger area and discover places like Willard Beach and Casco Bay Lines Ferry Terminal.
Meetinghouse Hill
While Meetinghouse Hill isn't home to many top sights, Willard Beach and Victoria Mansion are some notable places to visit nearby.
Willard
While Willard might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Willard Beach and Victoria Mansion.
Pleasantdale
Though Pleasantdale might not have many top sights, you can venture to the surrounding area to see attractions like Victoria Mansion and Portland Museum of Art.
South Portland Beach Vacation
Listen to the soothing sound of waves rolling into the shore and stroll by the shimmering waters during your South Portland vacation. 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 vacation deals to choose from. Book one close to Willard Beach, just 2 kilometres from the downtown area, and live out your vacation 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 vacation 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 vacation deals, you can see more top attractions like these.
Ready to book your vacation to South Portland?
South Portland Hotel Deals
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
CA $101
CA $110 total
Nov 11 - Nov 12
includes taxes & fees
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Fully refundable
CA $125
CA $136 total
Nov 3 - Nov 4
includes taxes & fees
8.4/10 Very good! (2,957 reviews)
"Kind staff, checked out about 30 minutes late but they were very accommodating."
Reviewed on Oct 24, 2026
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Fully refundable
CA $71
CA $78 total
Nov 22 - Nov 23
includes taxes & fees
7.2/10 Good! (997 reviews)
"Rooms were clean and comfortable. Parking was a little dark. Staff was very friendly and helpful. Outside looked a little unkept."
Reviewed on Oct 24, 2026
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.
Stay near popular South Portland attractions
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.
Fort Preble
8.8/10 (129 reviews)
On the South Portland waterfront, survey the scene of the Battle of Portland Harbor, which is the only known Civil War conflict fought in Maine.
Lyric Music Theater
7.4/10 (61 reviews)
You can enjoy a show at Lyric Music Theater during your trip to South Portland. Experience the area's acclaimed theater scene or attend a sporting event.
Maine Mall
8.4/10 (1,708 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.
Willard Beach
8.2/10 (161 reviews)
Why not spend a carefree afternoon at Willard Beach during your travels in South Portland?
South Portland Historical Society Museum
8.0/10 (84 reviews)
You can spend an afternoon exploring the galleries in South Portland Historical Society Museum during your travels in South Portland. Experience the area's great live music and acclaimed theater scene.
Maine Military Museum
7.8/10 (83 reviews)
You can spend an afternoon exploring the galleries in Maine Military Museum during your travels in South Portland. Experience the area's entertainment choices and great live music.
What to do in South Portland
Afternoon Windjammer Cruise Along the Coast of Portland Maine
CA $98
per adult
96% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
CA $109
per adult
92% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
CA $83
per adult
80% of travellers recommend
Frequently asked questions
How much does a South Portland vacation package cost?
You can snap up a vacation package to this destination from CA $1,251 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?
- Pick your travel dates: What you plan to do in South Portland and your preferred season will help you decide when to get away.
- 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.
- 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.
- 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.
Explore a world of travel with Expedia
- Hotels near Maine Mall
- Oceanfront Hotels in Old Orchard Beach
- Blind Tiger Portland
- Motels in Scarborough
- Portland Hotels
- Waves Oceanfront Resort
- Quality Inn & Suites South Portland
- Alouette Beach Resort
- Beach Hotel Hotels in Old Orchard Beach
- Doubletree by Hilton Hotel Portland
- Family Hotels in Portland
- Holiday Inn Express Hotel & Suites South Portland by IHG
- Oceanfront Hotels in Portland
- Cottages in Portland
- Inns in South Portland
- Hotels with Free Airport Shuttle in Portland
- Old Orchard Beach Hotels
- Hotels near Portland Intl. Jetport
- Ogunquit Hotels
- Hotels near Cross Insurance Arena
- Pet-Friendly Hotels in Portland
- Boutique Hotels in Portland
- Tru by Hilton Portland Airport Area
- Cheap Hotels in South Portland
- Old Port Hotels
- Hotels with Kitchenettes in Portland
- Hotels near Thompson's Point
- Inn By The Sea
- Motels in Portland
- Kennebunkport Hotels
- Downtown Portland Hotels
- Long Creek Hotel by IHG
- Freeport Hotels
- Hotels with Free Parking in Portland
- Portland Sheraton at Sable Oaks
- B&B in Portland
- Cheap Hotels in Portland
- Cabin Rentals in Portland
- Clarion Pointe South Portland
- Best Western Merry Manor Inn
- Home2 Suites by Hilton Portland Airport
- South Portland Hotels
- Comfort Inn South Portland Airport
- Courtyard by Marriott Portland Airport
- Cottages in Old Orchard Beach
- Flights from Winnipeg (YWG) to Portland (PWM)
- Flights from Fredericton (YFC) to Portland (PWM)
- Flights from Buffalo (BUF) to Portland (PWM)
- Flights from Moncton (YQM) to Portland (PWM)
- Flights from Montreal (YUL) to Portland (PWM)
- Flights from Detroit (DTW) to Portland (PWM)
- Flights from Ottawa (YOW) to Portland (PWM)
- Flights from Edmonton (YEG) to Portland (PWM)
- Flights from Toronto (YYZ) to Portland (PWM)
- Flights from Saint John (YSJ) to Portland (PWM)
- Flights from Portland Intl. Jetport
- Flights from Halifax (YHZ) to Portland (PWM)
- Flights from Vancouver (YVR) to Portland (PWM)
- Flights from Boston (BOS) to Portland (PWM)
- Flights from Calgary (YYC) to Portland (PWM)
- Flights to Portland
- Old Orchard Beach Vacations
- Camp Ellis Beach
- Ogunquit Beach
- Portland Vacations
- Bailey Island Vacations
- Higgins Beach
- Scarborough Beach State Park
- Desert of Maine
- Walker's Point
- Kennebunkport Vacations
- Kennebunkport Village Green
- Maine Mall
- Visit Ferry Village
- Marden's Surplus and Salvage
- Gooch's Beach
- Visit Old Orchard Beach
- Westbrook Vacations
- Popham Beach State Park
- Visit Old Port
- Portland Head Light
- Freeport Vacations
- Aquaboggan Water Park
- Ocean Park Vacations
- Palace Playland
- Ll Bean Flagship Store
- Windham Vacations
- Scarborough Vacations
- Old Orchard Beach Pier
- St. Anthony's Franciscan Monastery
- Visit Portland
- Portland Museum of Art
- Seashore Trolley Museum
- East End Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
