Book Holiday Homes in Cundys Harbor

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Featured Holiday Homes in Cundys Harbor

Fantastic Waterfront Views

Fantastic Waterfront Views

Phippsburg ME
The price is AU$562 per night from 21 Jan to 22 Jan
AU$562
21 Jan - 22 Jan 2026
includes taxes & fees
With a stay at this vacation home in Phippsburg (West Point), you'll be within a 15-minute drive of Casco Bay and Popham Beach State Park.
Opens in a new windowFantastic Waterfront Views
Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.

Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.

Boothbay Harbor ME
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 ...
Opens in a new windowNewly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.
Captain's Guest Room w/private bath. Walk to everything.

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

Bath ME
With a stay at this vacation home in Bath, you'll be within a 10-minute walk of Chocolate Church and Markings Gallery.
Opens in a new windowCaptain's Guest Room w/private bath. Walk to everything.
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Large, light filled 4 bedroom house - walk to ocean and ferry

Large, light filled 4 bedroom house - walk to ocean and ferry

Peaks Island ME
With a stay at this vacation home in Peaks Island, you'll be by the ocean, just a 1-minute walk from Casco Bay and 7 minutes by foot from Umbrella Cover ...
Opens in a new windowLarge, light filled 4 bedroom house - walk to ocean and ferry
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 ME
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 ...
Opens in a new windowDowntown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
Windward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock

Windward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock

Woolwich ME
Located in Woolwich, this vacation home is within a 5-minute drive of Kennebec River and Markings Gallery.
Opens in a new windowWindward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock
Beautiful house on the Harpswell Peninsula over looking Casco Bay

Beautiful house on the Harpswell Peninsula over looking Casco Bay

Harpswell ME
With a stay at this vacation home in Harpswell, you'll be by the ocean, just steps from Casco Bay and a 4-minute drive from Mitchell Field.
Opens in a new windowBeautiful house on the Harpswell Peninsula over looking Casco Bay
Lone Pine Cottage Maine - Chef’s Kitchen

Lone Pine Cottage Maine - Chef’s Kitchen

Bath ME
When you stay at this vacation home in Bath, you'll be by the sea, within a 15-minute walk of Maine Maritime Museum and Kennebec River.
Opens in a new windowLone Pine Cottage Maine - Chef’s Kitchen
Spectacular Oceanfront Estate with Beautiful Sunsets on 8 acres

Spectacular Oceanfront Estate with Beautiful Sunsets on 8 acres

Harpswell ME
With a stay at this vacation home in Harpswell, you'll be on the waterfront, just steps from Casco Bay and a 5-minute drive from Lower Goose Island.
Opens in a new windowSpectacular Oceanfront Estate with Beautiful Sunsets on 8 acres
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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
462 Holiday Homes
Lowest Price
AU$152
Highest Price
AU$562
Popular accommodation
Fantastic Waterfront Views, Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH., Captain's Guest Room w/private bath. Walk to everything., Large, light filled 4 bedroom house - walk to ocean and ferry, Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views, Windward Lodge- stunning, dog-friendly private waterfront retreat. Seasonal dock, Beautiful house on the Harpswell Peninsula over looking Casco Bay, Lone Pine Cottage Maine - Chef’s Kitchen, Spectacular Oceanfront Estate with Beautiful Sunsets on 8 acres

Top trending hotels in Cundys Harbor

Hilton Garden Inn Freeport Downtown

Hilton Garden Inn Freeport Downtown

3 out of 5
5 Park St Freeport ME
Fully refundableReserve now, pay when you stay
The price is AU$172 per night from 4 Jan to 5 Jan
AU$172
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at Hilton Garden Inn Freeport Downtown, you'll be centrally located in Freeport, within a 10-minute walk of LL Bean Flagship Store and Harrington ...
Opens in a new windowHilton Garden Inn Freeport Downtown
Comfort Inn Brunswick

Comfort Inn Brunswick

2.5 out of 5
199 Pleasant St Brunswick ME
Fully refundableReserve now, pay when you stay
The price is AU$152 per night from 3 Jan to 4 Jan
AU$152
3 Jan - 4 Jan 2026
includes taxes & fees
With a stay at Comfort Inn Brunswick, you'll be centrally located in Brunswick, within a 15-minute drive of LL Bean Flagship Store and Casco Bay.
Opens in a new windowComfort Inn Brunswick
Holiday Inn Express Hotel & Suites Freeport by IHG

Holiday Inn Express Hotel & Suites Freeport by IHG

2.5 out of 5
450 U.S. Route 1 Freeport ME
Fully refundable
The price is AU$153 per night from 28 Dec to 29 Dec
AU$153
28 Dec - 29 Dec
includes taxes & fees
With a stay at Holiday Inn Express Hotel & Suites Freeport by IHG in Freeport, you'll be within a 5-minute drive of LL Bean Flagship Store and Casco Bay.
Opens in a new windowHoliday Inn Express Hotel & Suites Freeport by IHG
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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 1 Jan to 2 Jan
AU$206
1 Jan - 2 Jan 2026
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
Don't see what you're looking for?
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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.