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

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 2 Sept to 3 Sept
S$216
2 Sept - 3 Sept
includes taxes & fees
7.8/10 Good! (1,009 reviews)
"Consistent- we’ve chosen to stay many times both when we need Park and Fly and when going to local concerts at Thompson Point so we can walk over, and have the long drive home late at night. Clean, friendly and convenient. Price is reasonable."

Reviewed on 23 Aug, 2025

Clarion Hotel Portland
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$213 per night from 31 Aug to 1 Sept
S$213
31 Aug - 1 Sept
includes taxes & fees
7.8/10 Good! (1,237 reviews)
ok stay
"They have an elevator, but front door is NOT handicapped accessible with automatic doors. Doors are not secured. Luggage carts available. Shampoo and liquid soap in the shower. Bathroom very small. Bed was uncomfortable. Rooms fairly quiet. Open air, easy self parking. Breakfast was good (cereal, ..."

Reviewed on 24 Aug, 2025

Days Inn by Wyndham Airport/Maine Mall
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
The price is S$126 per night from 15 Sept to 16 Sept
S$126
15 Sept - 16 Sept
includes taxes & fees
7.4/10 Good! (188 reviews)
"Enjoyed the pool and the tavern."

Reviewed on 27 Aug, 2025

Germaine Inn South Portland
See all 2,441 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 seaside 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$9
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
Portland: Sightseeing Cruise to Portland Head Light

Portland: Sightseeing Cruise to Portland Head Light

S$53
per adult
98% of travellers recommend
Portland: Sightseeing Cruise to Portland Head Light
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.