Southport Vacation Packages

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Your Southport Vacation

Enjoy amazing adventures when you lock in a Southport vacation package. Whether you're a foodie, art enthusiast or just a traveler who loves to experience new places, there's something for everyone in this exciting city. A trip to Southport is a wonderful opportunity to see the sights. Be sure to visit popular attractions like Coastal Maine Botanical Gardens, Boothbay Harbor Marina and Cabbage Island. A few clicks is all it takes to craft your ideal Southport vacation on Expedia.

Top Southport Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Cornish Inn

The Cornish Inn

3 out of 5
Price was CA $1,251, price is now CA $1,091 per person
CA $1,091
per person
Aug 5 - Aug 12
found 13 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
9.2/10 Wonderful! (59 reviews)
comfortable beds, clean room, nice having bar & restaurant in same building, would be helpful to have grab bar in the shower

Reviewed on Jun 10, 2026

USA Inn

USA Inn

2.5 out of 5
Price was CA $1,581, price is now CA $1,268 per person
CA $1,268
per person
Aug 5 - Aug 12
found 13 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
8/10 Very good! (797 reviews)
Everything was good room was nice but just didnt like the bathroom it was small. Cleaning staff keeped it clean & front desk was very nice..

Reviewed on Jul 1, 2026

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was CA $1,852, price is now CA $1,615 per person
CA $1,615
per person
Aug 27 - Aug 30
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,682 reviews)
Great location right in the heart of the Old Port District. The hotel is showing its age such as physical keys, and our smoke detector went off several times, but overall it was a nice place for a get-away.

Reviewed on Jul 4, 2026

The Majestic Regency Resort

The Majestic Regency Resort

2.5 out of 5
Moody
Price was CA $1,506, price is now CA $1,315 per person
CA $1,315
per person
Aug 5 - Aug 12
found 13 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
7/10 Good! (1,010 reviews)
Not the newest place but it served exactlywhat we needed

Reviewed on Jul 4, 2026

The Bethel Resort & Suites

The Bethel Resort & Suites

3 out of 5
Price was CA $1,415, price is now CA $1,244 per person
CA $1,244
per person
Aug 5 - Aug 12
found 13 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
7.8/10 Good! (400 reviews)
Staff was very pleasant and helpful. Property was nice but a bit tired……could use some upkeep. Gym was dirty and outdoor pool wasn’t really heated. For the price, I would have expected better.

Reviewed on Jun 22, 2026

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Southport Hotel Deals

Ocean Gate Inn

Ocean Gate Inn

3 out of 5
70 Ocean Gate Rd Southport ME
The price is CA $352 per night from Jul 12 to Jul 13
CA $352
CA $402 total
Jul 12 - Jul 13
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Great location. Staff was very friendly and helpful. Breakfast was good! Very clean and nice size room."

Reviewed on Jul 4, 2026

Ocean Gate Inn
Newagen Seaside Inn

Newagen Seaside Inn

3.5 out of 5
60 Newagen Colony Southport ME
The price is CA $317 per night from Jul 8 to Jul 9
CA $317
CA $384 total
Jul 8 - Jul 9
includes taxes & fees
9.4/10 Exceptional! (351 reviews)
"No where in the write up about this property did it say that were were steep steps that you have to climb with luggage to the 2nd floor. I needed to hotel with an elevator."

Reviewed on Jun 27, 2026

Newagen Seaside Inn
Generational Southport Property w/ Private Beach Newly Available for Rent!

Generational Southport Property w/ Private Beach Newly Available for Rent!

Southport ME
Get rates
Generational Southport Property w/ Private Beach Newly Available for Rent!
See all 1,494 properties in Southport
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.
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Stay near popular Southport attractions

Hendricks Head Beach

9.6/10 (14 reviews)
Why not spend a lazy afternoon at Hendricks Head Beach during your trip to Southport? Amble around this relaxing area's waterfront, or seek out the canoeing opportunities.
See properties

Frequently asked questions

How much does a Southport vacation package cost?
You'll find cheap prices from CA $1,091 on Expedia for your Southport getaway. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Southport costs.
What are the cheapest months to go to Southport?
Travel in the low season and you're likely to find cheap Southport vacation packages. Bear in mind that public holidays and local festivals and events can have an impact on prices, so do some research before you go.
How many days is enough for Southport?
Generally, a handful of days is enough to check out the top sights during your Southport vacation. However, if you want to have more time to relax or take day tours, consider extending your trip.
Is it worth booking a vacation package to Southport?
Southport is a good vacation destination with attractions like Hendricks Head Beach among the many things to keep you entertained. Whether you're heading away with the family or getting away with friends, a Southport vacation promises a good time for everyone.
How to find the best Southport package deals?
Begin your search for a Southport package deal by entering your travel dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Southport package deal straight away, simply play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Southport adventure off to a flying start.
Is it cheaper to book a Southport vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Southport vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Southport?
If you're considering a spontaneous Southport adventure, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Southport?

  1. Choose when to go: Check your schedule and get packing. Your preferred time of year and the activities on offer will also help you decide when to visit Southport.
  2. Budget wisely: On top of the cost of your hotel, you'll need to factor in other expenses too. These include flights, transportation and food. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Southport.
  3. Decide how long to go for: Now that you're more familiar with Southport, you can figure out the ideal length of your vacation. Pull together a rough itinerary and give yourself enough time to get through everything on your must-do list.
  4. Bundle your airfare and accommodations: Once you've nailed down your travel dates and duration, lock in the perfect Southport vacation package for you.

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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.