Great Diamond Island Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Robbie Martin
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    Better together
    Save up to NZ$545 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Our pick of the best Great Diamond Island Hotel Deals

Casco Bay Hotel, Ascend Hotel Collection
Casco Bay Hotel, Ascend Hotel Collection
3.5 out of 5
80 John Roberts Rd., South Portland, ME
Fully refundableReserve now, pay when you stay
The price is NZ$148 per night from 1 May to 2 May
NZ$148
per night
1 May - 2 May
8.6/10 Excellent! (1,404 reviews)
"Everything was great except it was raining and there is no covered enterance to load and unload the luggage."

Reviewed on 17 Apr. 2024

Casco Bay Hotel, Ascend Hotel Collection
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 NZ$300 per night from 22 Apr to 23 Apr
NZ$300
per night
22 Apr - 23 Apr
9/10 Wonderful! (1,147 reviews)
"Great stay in Portland. A favorite hotel on our two week trip to Maine and Atlantic Canada."

Reviewed on 18 Apr. 2024

Portland Harbor Hotel
The Westin Portland Harborview
The Westin Portland Harborview
4 out of 5
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is NZ$304 per night from 22 Apr to 23 Apr
NZ$304
per night
22 Apr - 23 Apr
8.4/10 Very Good! (1,060 reviews)
"."

Reviewed on 15 Apr. 2024

The Westin Portland Harborview
See all 2,140 properties in Great Diamond Island
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.

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.

Discover the most popular places to visit in Great Diamond Island

Image for Portland Head Light

Portland Head Light

4.5/5(4 reviews)

Look out across the Atlantic Ocean from Portland’s iconic white lighthouse, which has presided over the southern Maine coastline since the 18th century.

Portland Head Light
Image for LL Bean Flagship Store

LL Bean Flagship Store

5/5(1 review)

During your visit to Freeport, you can enjoy retail therapy at LL Bean Flagship Store. Stroll along the area's waterfront or simply enjoy its seafood restaurants.

LL Bean Flagship Store
Image for State Theatre

State Theatre

The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.

State Theatre

What to do in Great Diamond Island

Image for Portland: Old Port Seafood Lovers Tour

Portland: Old Port Seafood Lovers Tour

NZ$237
Per adult
Portland: Old Port Seafood Lovers Tour
Image for A Walk Through Time Tour in Portland

A Walk Through Time Tour in Portland

NZ$79
Per adult
96% of travellers recommend
A Walk Through Time Tour in Portland
Image for Audio Guided Walking Tour from Old Port of Portland, Maine

Audio Guided Walking Tour from Old Port of Portland, Maine

NZ$11
Per adult
Audio Guided Walking Tour from Old Port of Portland, Maine
See all activities in Great Diamond Island
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.