Great Diamond Island Holidays

  • Plan, book, travel with confidence

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Great Diamond Island

Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
22 Mckinley Court, Great Diamond Island, Portland, ME
Fully refundableReserve now, pay when you stay
The price is S$541 per night from 3 Aug to 4 Aug
S$541
3 Aug - 4 Aug
includes taxes & fees
8.8/10 Excellent! (180 reviews)
"Such an amazing property, felt like stepping into a Hallmark movie, the rooms were spacios and decorated beautifully, the staff was amzing. I wish I could have stayed there for at least a week."

Reviewed on 15 Jul, 2025

Inn at Diamond Cove
Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is S$209 per night from 20 Jul to 21 Jul
S$209
20 Jul - 21 Jul
includes taxes & fees
7.8/10 Good! (1,035 reviews)
"We were there for one night, a travel stopover. The room, bed, service, etc. were all perfectly fine for that kind of stay. I probably wouldn't want to stay a week, but for an overnight, it was OK."

Reviewed on 17 Jul, 2025

Days Inn by Wyndham Airport/Maine Mall
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is S$216 per night from 31 Jul to 1 Aug
S$216
31 Jul - 1 Aug
includes taxes & fees
7.8/10 Good! (1,007 reviews)
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Reviewed on 19 Jul, 2025

Clarion Hotel Portland
See all 2,509 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.

Popular places to visit

Thompson's Point

Commune with nature and explore the great outdoors at Thompson's Point during your travels in Portland. Stroll along the waterfront or attend a sporting event in the area.

Thompson's Point

What to do in Great Diamond Island

Portland Downtown Highlights: "The Golden Adventure" Exploration Game

Downtown Golden Adventure Quest Experience in Portland

S$11
per adult
Downtown Golden Adventure Quest Experience in Portland
Afternoon Windjammer Cruise Along the Coast of Portland Maine

Afternoon Windjammer Cruise Along the Coast of Portland Maine

S$86
per adult
Afternoon Windjammer Cruise Along the Coast of Portland Maine
Sunset Lighthouse Cruise Tour from Casco Bay

Sunset Lighthouse Cruise Tour from Casco Bay

S$72
per adult
90% of travellers recommend
Sunset Lighthouse Cruise Tour from Casco Bay
See all activities in Great Diamond Island

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.