Great Diamond Island Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Top hotels in Great Diamond Island

La Quinta Inn & Suites by Wyndham Portland
La Quinta Inn & Suites by Wyndham Portland
2.5 out of 5
340 Park Ave, Portland, ME
Fully refundableReserve now, pay when you stay
The price is S$123 per night from 22 Dec to 23 Dec
S$123
includes taxes & fees
22 Dec - 23 Dec
8.8/10 Excellent! (2,017 reviews)
Great stay, middling breakfast
"I enjoyed my stay, room was quiet, slept well 4 nights!!! Only downside was skimpy breakfast compared to la quinta in Harrisburg earlier on our trip."

Reviewed on 20 Nov,2024

La Quinta Inn & Suites by Wyndham Portland
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$104 per night from 14 Dec to 15 Dec
S$104
includes taxes & fees
14 Dec - 15 Dec
8.4/10 Very Good! (2,376 reviews)
"Very good"

Reviewed on 22 Nov,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$238 per night from 3 Dec to 4 Dec
S$238
includes taxes & fees
3 Dec - 4 Dec
9/10 Wonderful! (1,398 reviews)
Good place to getaway to.
"The hotel is wonderful. They seemed very short on staff. Coffee and tea stations were sparsely stocked. Always out of coffee. The menu for dinner at the restaurant could be greatly improved and have a few more offerings. The breakfast staff was inexperienced and very understaffed. Other than that ..."

Reviewed on 19 Nov,2024

Portland Harbor Hotel
See all 2,174 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

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$14
Per adult
Downtown Golden Adventure Quest Experience in Portland
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

S$12
Per adult
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
Enjoying lobster rolls

Old Port "Seafood Lovers" Walking Lunch Tour in Portland, Maine

S$197
Per adult
100% of travellers recommend
Old Port "Seafood Lovers" Walking Lunch Tour in 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. 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.