Great Diamond Island Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
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Great Diamond Island Holiday
Our pick of the best Great Diamond Island Hotel Deals
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
NZ$162
27 Oct - 28 Oct
includes taxes & fees
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
NZ$211
18 Nov - 19 Nov
includes taxes & fees
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
NZ$174
25 Oct - 26 Oct
includes taxes & fees
8.2/10 Very good! (1,006 reviews)
"This was a great little spot- close to downtown Portland (about 15 mins). Very cozy rooms and I loved the hot tub. I want to go back in the summer to enjoy the beautiful patio (my trip was during a cold September weekend). Staff were friendly and helpful and their grab and go breakfast had tons of ..."
Reviewed on 20 Oct 2026
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.
What to do in Great Diamond Island
Afternoon Windjammer Cruise Along the Coast of Portland Maine
NZ$121
per adult
96% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
NZ$103
per adult
80% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
NZ$135
per adult
90% of travellers recommend
Frequently asked questions
How much does a Great Diamond Island holiday package cost?
Less than you might think — from just , as a matter of fact! By combining hotels, flights and car rentals into your own custom-built travel package, your getaway to Great Diamond Island is just clicks away.
How do I get a cheap travel package to Great Diamond Island?
Bundle your hotel and flight bookings, throw in extras such as activities or a rental car, and save with a Great Diamond Island holiday package. You won't just walk away with awesome discounts on your adventure — you'll have loads of choice at your fingertips too. When you book with Expedia, you'll have your pick of over 550 partner airlines and 1 000 000 hotels worldwide. Your dream holiday starts right here, right now!
How far in advance should I book my Great Diamond Island holiday?
Smart travellers often book as early as possible. You can usually look up international airfares on Expedia up to 12 months before your flight. If you've left booking to the last minute, don't despair. Bargain prices sometimes appear just weeks prior to departure.
What does an Expedia Great Diamond Island travel package include?
Hotels, flights and rental cars, or any combination of them — it's totally up to you. Whether you're venturing to Great Diamond Island with the kids or adventuring solo, there's a package to suit your budget and style. Once you've made your booking, why not add on some tours or activities?
What should I know before booking a Great Diamond Island travel package?
When you book your hotels, flights and car rentals together, you'll score awesome discounts. Whether you're organising a rural escape in a cottage or would rather stay in a fancy hotel in the city, Expedia can help make it happen.
Can I choose my airline with a Great Diamond Island Expedia holiday package?
You sure can. We have more than 550 partner airlines around the world, so opt for the carrier that fits your needs.
If I'm not able to travel, can I cancel my Great Diamond Island holiday package?
It's impossible to predict what the future holds, so it's comforting to know that you can cancel or change your Great Diamond Island holiday package. If your booking was made in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal for more information.
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- Brick Store Museum
- Portland Holidays
- Harrington House
- Maine Street
- Popham Beach State Park
- Poland Holidays
- Gooch's Beach
- Wedding Cake House
- Fort Williams Park
- Port City Music Hall
- Thompson's Point
- Aquaboggan Water Park
- Mother's Beach
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- State Street Church
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- Hunnewell Beach
- Visit Casco Bay Islands
- Visit Great Diamond Island
- Visit Old Port
- Visit Downtown Portland
- Scuba Diving Holiday Packages Casco Bay Islands
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
