Great Diamond Island Holidays

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    Save up to €185 when you book a flight and hotel together*
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Top hotels in Great Diamond Island

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 €109 per night from 24 Aug to 25 Aug
€109
24 Aug - 25 Aug
includes taxes & fees
7.8/10 Good! (1,144 reviews)
August 2025
"My daughter and I stayed here for 4 nights while apartment hunting in Portland. We had trouble with our keys working and they finally determined that each time they gave us a different key card, they were authorizing it for just one night. This is an older property but is reasonably well kept. There ..."

Reviewed on 9 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 €100 per night from 17 Aug to 18 Aug
€100
17 Aug - 18 Aug
includes taxes & fees
7.6/10 Good! (125 reviews)
"We loved the indoor pool, the breakfast, and the mural in the room!"

Reviewed on 6 Aug 2025

Germaine Inn South Portland
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is €123 per night from 1 Sept to 2 Sept
€123
1 Sept - 2 Sept
includes taxes & fees
7.6/10 Good! (1,040 reviews)
"."

Reviewed on 9 Aug 2025

Ramada Plaza by Wyndham Portland
See all 2,470 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

Portland Museum of Art which includes art and interior views as well as a small group of people

Portland Museum of Art

Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.

Portland Museum of Art
East End Beach showing a sandy beach and general coastal views as well as a small group of people

East End Beach

Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.

East End Beach
Wadsworth-Longfellow House showing interior views, heritage elements and a house

Wadsworth-Longfellow House

As you tour this historic brick home, trace three generations of Maine family history and learn about the cultural and political impact of its family members.

Wadsworth-Longfellow House

What to do in Great Diamond Island

Portland Downtown Highlights: "The Golden Adventure" Exploration Game

Downtown Golden Adventure Quest Experience in Portland

€6
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

€58
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

€51
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.