Book Holiday Homes in Great Diamond Island

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Great Diamond Island 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 Great Diamond Island vacation homes are the perfect way for you to wing it.

Holiday houses in Great Diamond Island 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 Great Diamond Island 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 Great Diamond Island adventures, obvs.

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

Great Diamond Island Holiday Homes essential information

Accommodation
Holiday Homes
Lowest Price
AU$117
Highest Price
AU$289
Popular accommodation
Portland Harbor Hotel, Holiday Inn Portland-By the Bay, an IHG Hotel, Cambria Hotel Portland Downtown-Old Port, DoubleTree by Hilton Hotel Portland

Top trending hotels in Great Diamond Island

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$289 per night from 25 Feb to 26 Feb
AU$289
includes taxes & fees
25 Feb - 26 Feb
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, a 5-minute drive from Thompson's Point and 9 minutes from Maine Mall.
Portland Harbor Hotel
Holiday Inn Portland-By the Bay, an IHG Hotel

Holiday Inn Portland-By the Bay, an IHG Hotel

3 out of 5
88 Spring St, Portland, ME
Fully refundable
The price is AU$173 per night from 13 Feb to 14 Feb
AU$173
includes taxes & fees
13 Feb - 14 Feb
With a stay at Holiday Inn Portland-By the Bay by IHG in Portland (Downtown Portland), you'll be a 4-minute drive from Thompson's Point and 8 minutes from Maine ...
Holiday Inn Portland-By the Bay, an IHG Hotel
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$214 per night from 17 Feb to 18 Feb
AU$214
includes taxes & fees
17 Feb - 18 Feb
Located in Portland (East Bayside), Cambria Hotel Portland Downtown-Old Port is within a 10-minute drive of Thompson's Point and Maine Mall.
Cambria Hotel Portland Downtown-Old Port
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DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
363 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$117 per night from 27 Feb to 28 Feb
AU$117
includes taxes & fees
27 Feb - 28 Feb
When you stay at DoubleTree by Hilton Hotel Portland in South Portland, you'll be near the airport, a 1-minute drive from Maine Mall and 8 minutes from Thompson's ...
DoubleTree by Hilton Hotel Portland
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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.