Book Holiday Homes in Cundys Harbor

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Featured Holiday Homes in Cundys Harbor

Captain's House 2BR Apartment. Walk to Everything!

Captain's House 2BR Apartment. Walk to Everything!

Bath
With a stay at this vacation home in Bath, you'll be within a 10-minute walk of Chocolate Church and Markings Gallery.
Captain's House 2BR Apartment. Walk to Everything!
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
Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer

Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer

2 out of 5
Boothbay
With a stay at this vacation home in Boothbay, you'll be by the sea, just steps from Hodgdon Island and a 2-minute drive from Coastal Maine Botanical ...
Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer
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Charming Oceanfront House with Deck, Cozy Loft, and Direct Beach Access

Charming Oceanfront House with Deck, Cozy Loft, and Direct Beach Access

Georgetown
Located in Georgetown, this vacation home is by the sea, within a 10-minute drive of Reid State Park and Georgetown Historical Society.
Charming Oceanfront House with Deck, Cozy Loft, and Direct Beach Access
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

Boothbay Harbor
With a stay at this vacation home in Boothbay Harbor, you'll be on the beach, just a 4-minute walk from Boothbay Harbor Memorial Library and 6 minutes by foot ...
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces

Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces

Westport
Located in Wiscasset, this vacation home is by the ocean, a 4-minute drive from Long Ledge and 6 minutes from Brooks Point.
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
Camp Forever cottage

Camp Forever cottage

Harpswell
Located in Harpswell, this vacation home is by the ocean, a 1-minute drive from Casco Bay and 9 minutes from Paddleworks.
Camp Forever cottage
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

Cumberland
With a stay at this vacation home, you'll be centrally located in Cumberland Center, within a 15-minute drive of State Theatre and Thompson's Point.
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
Downtown Boothbay Harbor, 2-Story Cottage

Downtown Boothbay Harbor, 2-Story Cottage

Boothbay Harbor
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 ...
Downtown Boothbay Harbor, 2-Story Cottage
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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.

Cundys Harbor 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 Cundys Harbor vacation homes are the perfect way for you to wing it.

Holiday houses in Cundys Harbor 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 Cundys Harbor 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 Cundys Harbor adventures, obvs.

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

Cundys Harbor Holiday Homes essential information

Accommodation
500 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Captain's House 2BR Apartment. Walk to Everything!, Oceanfront Cabin-Castle in Maine Woods, Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer, Charming Oceanfront House with Deck, Cozy Loft, and Direct Beach Access, Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views, Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces, Camp Forever cottage, Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!, Downtown Boothbay Harbor, 2-Story Cottage

Top trending hotels in Cundys Harbor

Best Western Freeport Inn

Best Western Freeport Inn

3 out of 5
31 US Route 1, Freeport, ME
Fully refundableReserve now, pay when you stay
With a stay at Best Western Freeport Inn in Freeport, you'll be within a 10-minute drive of LL Bean Flagship Store and Casco Bay.
Best Western Freeport Inn
Travelers Inn

Travelers Inn

2 out of 5
130 Pleasant St, Brunswick, ME
Fully refundableReserve now, pay when you stay
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
Casco Bay Inn

Casco Bay Inn

2 out of 5
107 US Route 1, Freeport, ME
Fully refundableReserve now, pay when you stay
With a stay at Casco Bay Inn in Freeport, you'll be within a 10-minute drive of LL Bean Flagship Store and Casco Bay.
Casco Bay Inn
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The Harraseeket Inn & Event House

The Harraseeket Inn & Event House

3.5 out of 5
162 Main St, Freeport, ME
Fully refundableReserve now, pay when you stay
The Harraseeket Inn & Event House is in the heart of Freeport, within a 10-minute walk of Casco Bay and LL Bean Flagship Store.
The Harraseeket Inn & Event House
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^Subject to availability and chosen travel dates.