Book Holiday Homes in South Bristol

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Featured Holiday Homes in South Bristol

Beautiful Oceanfront House- Stunning Water Views

Beautiful Oceanfront House- Stunning Water Views

Harpswell ME
When you stay at this vacation home in Harpswell, you'll be within a 10-minute drive of Androscoggin River and Brunswick Naval Aviation Museum.
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$675 per night from 19 May to 20 May
AU$675
19 May - 20 May
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. Discover the authenticity & great value!

Captain's Guest Room. Discover the authenticity & great value!

Bath ME
The price is AU$207 per night from 19 May to 20 May
AU$207
19 May - 20 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. Discover the authenticity & great value!
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.

South Bristol 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 South Bristol vacation homes are the perfect way for you to wing it.

Holiday houses in South Bristol 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 South Bristol 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 South Bristol adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in South Bristol 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 South Bristol 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.

South Bristol Holiday Homes essential information

Accommodation
404 Holiday Homes
Lowest Price
AU$187
Highest Price
AU$675
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. Discover the authenticity & great value!, 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 South Bristol

Residence Inn Bath Brunswick Area

Residence Inn Bath Brunswick Area

3 out of 5
139 Richardson St. Bath ME
Fully refundableReserve now, pay when you stay
The price is AU$206 per night from 24 May to 25 May
AU$206
24 May - 25 May
includes taxes & fees
Located in Bath, Residence Inn Bath Brunswick Area is within a 5-minute drive of Casco Bay and Bath Visitor Information Center.
Opens in a new windowResidence Inn Bath Brunswick Area
Tugboat Inn

Tugboat Inn

3 out of 5
80 Commercial St. Boothbay Harbor ME
The price is AU$274 per night from 19 May to 20 May
AU$274
19 May - 20 May
includes taxes & fees
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.
Opens in a new windowTugboat Inn
Smuggler's Cove Inn

Smuggler's Cove Inn

2.5 out of 5
727 Ocean Point Road East Boothbay ME
The price is AU$291 per night from 19 May to 20 May
AU$291
19 May - 20 May
includes taxes & fees
Located in East Boothbay, Smuggler's Cove Inn is by the ocean, within a 10-minute drive of Boothbay Harbor Memorial Library and Boothbay Harbor Marina.
Opens in a new windowSmuggler's Cove Inn
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Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
200 Townsend Avenue Boothbay Harbor ME
The price is AU$187 per night from 19 May to 20 May
AU$187
19 May - 20 May
includes taxes & fees
With a stay at Flagship Inn and Suites in Boothbay Harbor, you'll be a 1-minute walk from Carousel Music Theater and 6 minutes by foot from Boothbay Region Land ...
Opens in a new windowFlagship Inn and Suites
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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.