Book Holiday Homes in Southport

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Featured Holiday Homes in Southport

Beautiful Oceanfront House- Stunning Water Views

Beautiful Oceanfront House- Stunning Water Views

Harpswell ME
Located in Harpswell, this vacation home is a 1-minute drive from Casco Bay and 7 minutes from Androscoggin River.
Opens in a new windowBeautiful Oceanfront House- Stunning Water Views
Boothbay Harbor Woodland Retreat

Boothbay Harbor Woodland Retreat

Boothbay Harbor ME
With a stay at this vacation home in Boothbay Harbor, you'll be within a 5-minute drive of Boothbay Harbor Marina and Burnt Island Living Lighthouse.
Opens in a new windowBoothbay Harbor Woodland Retreat
Centerview cottage

Centerview cottage

Harpswell ME
The price is AU$657 per night from 14 June to 15 June
AU$657
14 June - 15 June
includes taxes & fees
Located in Harpswell, this vacation home is by the ocean, within a 15-minute drive of Paddleworks and Bailey Island Bridge.
Opens in a new windowCenterview cottage
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Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE

Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE

East Boothbay ME
A stay at this vacation home places you in the heart of East Boothbay, within a 5-minute drive of Linekin Bay and Grimes Cove Beach.
Opens in a new windowSmuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE
Downtown Waterfront Cottage with shoreline sitting room

Downtown Waterfront Cottage with shoreline sitting room

Boothbay Harbor ME
With a stay at this vacation home, you'll be centrally located in Boothbay Harbor, just a 4-minute walk from Boothbay Harbor Memorial Library and 5 minutes by ...
Opens in a new windowDowntown Waterfront Cottage with shoreline sitting room
Captain's Guest Room w/private bath. Walk to everything.

Captain's Guest Room w/private bath. Walk to everything.

Bath ME
The price is AU$204 per night from 16 May to 17 May
AU$204
16 May - 17 May
includes taxes & fees
With a stay at this vacation home in Bath, you'll be within a 10-minute walk of Chocolate Church Arts Center and Bath Center for the Arts.
Opens in a new windowCaptain's Guest Room w/private bath. Walk to everything.
Summer 2026 ! Kayak on the Kennebec " EVERYTHING you need "

Summer 2026 ! Kayak on the Kennebec " EVERYTHING you need "

Phippsburg ME
A stay at this vacation home places you in the heart of Phippsburg, a 1-minute drive from Casco Bay and 7 minutes from Maine Maritime Museum.
Opens in a new windowSummer 2026 ! Kayak on the Kennebec " EVERYTHING you need "
Downtown Boothbay Harbor, 2-Story Cottage

Downtown Boothbay Harbor, 2-Story Cottage

Boothbay Harbor ME
With a stay at this vacation home in Boothbay Harbor, you'll be within a 5-minute walk of Opera House at Boothbay Harbor and Boothbay Region Historical Society ...
Opens in a new windowDowntown Boothbay Harbor, 2-Story Cottage
Peaceful Georgetown Retreat with Water Views, Near Reid State and Popham

Peaceful Georgetown Retreat with Water Views, Near Reid State and Popham

Georgetown ME
With a stay at this vacation home in Georgetown, you'll be on the waterfront, a 4-minute walk from Georgetown Pottery and a 3-minute drive from Sewell Pond Conservation ...
Opens in a new windowPeaceful Georgetown Retreat with Water Views, Near Reid State and Popham
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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.

Southport Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Southport vacation homes are the perfect way for you to wing it.

Holiday houses in Southport let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Southport in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Southport adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Southport with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Southport vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Southport Holiday Homes essential information

Accommodation
495 Holiday Homes
Lowest Price
AU$204
Highest Price
AU$657
Popular accommodation
Beautiful Oceanfront House- Stunning Water Views, Boothbay Harbor Woodland Retreat, Centerview cottage, Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE, Downtown Waterfront Cottage with shoreline sitting room, Captain's Guest Room w/private bath. Walk to everything., Summer 2026 ! Kayak on the Kennebec " EVERYTHING you need ", Downtown Boothbay Harbor, 2-Story Cottage, Peaceful Georgetown Retreat with Water Views, Near Reid State and Popham

Top trending hotels in Southport

Ocean Gate Inn

Ocean Gate Inn

3 out of 5
70 Ocean Gate Rd Southport ME
The price is AU$425 per night from 29 May to 30 May
AU$425
29 May - 30 May
includes taxes & fees
Located in Southport, Ocean Gate Inn is by the ocean, a 4-minute drive from Hendricks Hill Museum and 5 minutes from Juniper Point.
Opens in a new windowOcean Gate Inn
Newagen Seaside Inn

Newagen Seaside Inn

3.5 out of 5
60 Newagen Colony Southport ME
The price is AU$220 per night from 26 May to 27 May
AU$220
26 May - 27 May
includes taxes & fees
Located in Southport, Newagen Seaside Inn is by the ocean, a 1-minute drive from Southport Memorial Library and 5 minutes from Hendricks Hill Museum.
Opens in a new windowNewagen Seaside Inn
A Cozy Retreat on Southport Island

A Cozy Retreat on Southport Island

Southport ME
When you stay at this cottage in Southport, you'll be on the waterfront, within a 5-minute drive of Hendricks Hill Museum and Juniper Point.
Opens in a new windowA Cozy Retreat on Southport Island
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Enjoyable 1-bedroom rustic cottage in Southport.

Enjoyable 1-bedroom rustic cottage in Southport.

Southport ME
Located in Southport, this cottage is by the sea, a 4-minute drive from Hendricks Hill Museum and 6 minutes from Juniper Point.
Opens in a new windowEnjoyable 1-bedroom rustic cottage in Southport.
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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.

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