Great Diamond Island Holidays

Photo by Robbie Martin
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Top hotels in Great Diamond Island

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 S$144 per night from 27 May to 28 May
S$144
per night
27 May - 28 May
8.6/10 Excellent! (1,489 reviews)
"Very nice place"

Reviewed on 20 May,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 S$354 per night from 28 May to 29 May
S$354
per night
28 May - 29 May
9/10 Wonderful! (1,190 reviews)
"One of the best hotels we ever stayed in."

Reviewed on 20 May,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 S$259 per night from 28 May to 29 May
S$259
per night
28 May - 29 May
8.4/10 Very Good! (1,053 reviews)
"Excellent TV screen and easy channel options."

Reviewed on 19 May,2024

The Westin Portland Harborview
See all 2,165 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.

Popular places to visit

Image for LL Bean Flagship Store

LL Bean Flagship Store

4.5/5(4 reviews)

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 Portland Head Light

Portland Head Light

4.5/5(10 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 Old Orchard Beach

Old Orchard Beach

Why not spend a lazy afternoon at Old Orchard Beach during your trip to Old Orchard Beach? Wander the beautiful beaches and picturesque gardens in the area.

Old Orchard Beach

What to do in Great Diamond Island

Image for Portland: Old Port Seafood Lovers Tour

Portland: Old Port Seafood Lovers Tour

S$195
Per adult
Portland: Old Port Seafood Lovers Tour
Image for A Walk Through Time Tour in Portland

A Walk Through Time Tour in Portland

S$66
Per adult
96% of travellers recommend
A Walk Through Time Tour in Portland
Image for Sunset Lighthouse Harbor Cruise from Portland's Old Port

Sunset Lighthouse Harbor Cruise from Portland's Old Port

S$140
Per adult
Sunset Lighthouse Harbor Cruise from Portland's Old Port
See all activities in Great Diamond Island

More trip options

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.