Book Holiday Homes in Cundys Harbor

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Featured Holiday Homes in Cundys Harbor

Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor

Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor

Boothbay Harbor
With a stay at this vacation home in Boothbay Harbor, you'll be a 4-minute walk from Boothbay Harbor Memorial Library and 5 minutes by foot from Boothbay Harbor ...
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
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
Captain's Quarters  Guest Room w/Private Bath & Entrance. Best Value in Town!

Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

Bath
The price is AU$256 per night from 7 Aug to 8 Aug
AU$256
7 Aug - 8 Aug
includes taxes & fees
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 Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!
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Captain's House 2BR Apartment. Walk to Everything!

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

Bath
The price is AU$407 per night from 24 Aug to 25 Aug
AU$407
24 Aug - 25 Aug
includes taxes & fees
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!
NEW! Coveside! Designer decor, waterfront, AC, 2 Bedroom in Harpswell.

NEW! Coveside! Designer decor, waterfront, AC, 2 Bedroom in Harpswell.

Harpswell
Located in Harpswell, this vacation home is by the ocean, a 1-minute drive from Casco Bay and 9 minutes from Paddleworks.
NEW! Coveside! Designer decor, waterfront, AC, 2 Bedroom in Harpswell.
Elegant and efficient Island home 4 miles from downtown Portland

Elegant and efficient Island home 4 miles from downtown Portland

Portland
With a stay at this vacation home in Portland, you'll be steps from Casco Bay and a 3-minute drive from Little Diamond Island.
Elegant and efficient Island home 4 miles from downtown Portland
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 Thompson's Point and LL Bean Flagship ...
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
Well-located, dog-friendly home - walk to footbridge & Barrett Park

Well-located, dog-friendly home - walk to footbridge & Barrett Park

Boothbay Harbor
When you a stay at this vacation home in Boothbay Harbor, you'll be by the sea, just steps from Linekin Bay and Fisherman's Memorial Park.
Well-located, dog-friendly home - walk to footbridge & Barrett Park
Dog-friendly home with high-speed WiFi, washer/dryer, & private dock

Dog-friendly home with high-speed WiFi, washer/dryer, & private dock

Harpswell
Located in Harpswell, this vacation home is by the sea, a 1-minute drive from Casco Bay and 7 minutes from Ragged Island.
Dog-friendly home with high-speed WiFi, washer/dryer, & private dock
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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
539 Holiday Homes
Lowest Price
AU$208
Highest Price
AU$407
Popular accommodation
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor, Tranquil Seaside Cottage with Spectacular Views, Wifi & Washer/Dryer, Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!, Captain's House 2BR Apartment. Walk to Everything!, NEW! Coveside! Designer decor, waterfront, AC, 2 Bedroom in Harpswell., Elegant and efficient Island home 4 miles from downtown Portland, Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!, Well-located, dog-friendly home - walk to footbridge & Barrett Park, Dog-friendly home with high-speed WiFi, washer/dryer, & private dock

Top trending hotels in Cundys Harbor

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
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
The price is AU$208 per night from 31 Aug to 1 Sept
AU$208
31 Aug - 1 Sept
includes taxes & fees
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
Ocean Gate Resort

Ocean Gate Resort

3 out of 5
70 Ocean Gate Rd, Southport, ME
Fully refundableReserve now, pay when you stay
The price is AU$272 per night from 1 Sept to 2 Sept
AU$272
1 Sept - 2 Sept
includes taxes & fees
Located in Southport, Ocean Gate Resort is by the ocean, a 4-minute drive from Hendricks Hill Museum and 5 minutes from Juniper Point.
Ocean Gate Resort
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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$264 per night from 14 Aug to 15 Aug
AU$264
14 Aug - 15 Aug
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 ...
Flagship Inn and Suites
Don't see what you're looking for?
See all available properties in Cundys Harbor
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.