Book Holiday Homes in Southport

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Featured Holiday Homes in Southport

Admiral's Quarters - Room 12

Admiral's Quarters - Room 12

Boothbay Harbor
The price is AU$733 per night from 25 Nov to 26 Nov
AU$733
includes taxes & fees
25 Nov - 26 Nov
When you a stay at this vacation home in Boothbay Harbor, you'll be by the ocean, within a 5-minute walk of Burnt Island Living Lighthouse and Boothbay Harbor ...
Admiral's Quarters - Room 12
Oceanfront Cabin-Castle in Maine Woods

Oceanfront Cabin-Castle in Maine Woods

Georgetown
Located in Georgetown, this vacation home is by the ocean, a 1-minute drive from Reid State Park and 8 minutes from Georgetown Historical Society.
Oceanfront Cabin-Castle in Maine Woods
Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.

Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.

Boothbay Harbor
A stay at this vacation home places you in the heart of Boothbay Harbor, within a 5-minute walk of Boothbay Region Land Trust and Boothbay Region Historical ...
Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown.
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Full sized home

Full sized home

Harpswell
The price is AU$575 per night from 25 Nov to 26 Nov
AU$575
includes taxes & fees
25 Nov - 26 Nov
With a stay at this vacation home in Harpswell, you'll be by the sea, just steps from Casco Bay and a 3-minute drive from Ash Cove Pottery.
Full sized home
Quintessential Maine Oceanfront home

Quintessential Maine Oceanfront home

Bremen
When you stay at this vacation home in Bremen, you'll be on the beach and 10 minutes by car from Penobscot Marine Museum.
Quintessential Maine Oceanfront home
Home In Boothbay - Holiday Getaway

Home In Boothbay - Holiday Getaway

Boothbay
Located in Boothbay, this vacation home is in a rural location, within a 15-minute walk of The Boothbay Playhouse and Dolphin Mini Golf.
Home In Boothbay - Holiday Getaway
The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor

The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor

Boothbay Harbor
With a stay at this vacation home in Boothbay Harbor, you'll be on the waterfront, just a 3-minute walk from Opera House at Boothbay Harbor and 5 minutes by ...
The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor
Lowell's Getaway.  Kayaking, beaches, dining and AC from this water view home.

Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.

Harpswell
With a stay at this vacation home in Orrs Island, you'll be by the ocean, just a 1-minute walk from Casco Bay and 11 minutes by foot from Paddleworks.
Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.
Beautiful house on the Harpswell Peninsula over looking Casco Bay

Beautiful house on the Harpswell Peninsula over looking Casco Bay

Harpswell
With a stay at this vacation home in Harpswell, you'll be by the ocean, just steps from Casco Bay and a 5-minute drive from Lower Goose Island.
Beautiful house on the Harpswell Peninsula over looking Casco Bay
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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
384 Holiday Homes
Lowest Price
AU$114
Highest Price
AU$733
Popular accommodation
Admiral's Quarters - Room 12, Oceanfront Cabin-Castle in Maine Woods, Newly renovated 3 bedroom, 2 bath bungalow, walking distance to downtown., Full sized home, Quintessential Maine Oceanfront home, Home In Boothbay - Holiday Getaway, The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor, Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home., Beautiful house on the Harpswell Peninsula over looking Casco Bay

Top trending hotels in Southport

Stunning oceanfront cottage w/ private deck and Atlantic views

Stunning oceanfront cottage w/ private deck and Atlantic views

Southport
A stay at this vacation home places you in the heart of Southport, just a 3-minute walk from Southport Memorial Library and within a 5-minute drive of Hendricks ...
Stunning oceanfront cottage w/ private deck and Atlantic views
The Brunswick Hotel

The Brunswick Hotel

3 out of 5
4 Noble St, Brunswick, ME
Fully refundableReserve now, pay when you stay
The price is AU$201 per night from 24 Nov to 25 Nov
AU$201
includes taxes & fees
24 Nov - 25 Nov
A stay at The Brunswick Hotel places you in the heart of Brunswick, steps from Casco Bay and Maine Street.
The Brunswick Hotel
Tugboat Inn

Tugboat Inn

3 out of 5
80 Commercial St., Boothbay Harbor, ME
The price is AU$234 per night from 27 Nov to 28 Nov
AU$234
includes taxes & fees
27 Nov - 28 Nov
With a stay at Tugboat Inn in Boothbay Harbor, you'll be within a 5-minute walk of Burnt Island Living Lighthouse and Boothbay Harbor Marina.
Tugboat Inn
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Travelers Inn

Travelers Inn

2 out of 5
130 Pleasant St, Brunswick, ME
Fully refundableReserve now, pay when you stay
The price is AU$114 per night from 26 Nov to 27 Nov
AU$114
includes taxes & fees
26 Nov - 27 Nov
A stay at Travelers Inn places you in the heart of Brunswick, within a 5-minute drive of Bowdoin College and Maine State Music Theater.
Travelers Inn
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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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^Subject to availability and chosen travel dates.