Great Diamond Island Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Great Diamond Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Seabreeze Motel
CA $861
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
7.2/10 Good! (462 reviews)
Front desk was super helpful, location was good but the noise was a lot, could hear a the people above us a lot and then lots of chaos in the street plus the train.
Reviewed on Aug 30, 2026
Ogunquit River Inn & Suites
Moody
CA $1,153
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9/10 Wonderful! (1,022 reviews)
The property including room was very nice. It's on a main road but set down so there is no noise. Breakfast was good. The view from the yard in back was very beautiful and peaceful. People were enjoying the pool. The only slight area of improvement would be the efficient reception team's warmth quotient. Would stay again.
Reviewed on Sep 3, 2026
The Meadowmere Resort
CA $871
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
8.6/10 Excellent! (1,010 reviews)
Clean room, paid breakfast, front office staff very efficient, very limited items even in paid breakfast section.check in time 4 pm and check out 11 am.
Reviewed on Sep 2, 2026
Ready to book your vacation to Great Diamond Island?
Great Diamond Island Hotel Deals
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
CA $105
CA $114 total
Sep 10 - Sep 11
includes taxes & fees
6.4/10 (1,109 reviews)
"."
Reviewed on Sep 3, 2026
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Fully refundable
CA $161
CA $175 total
Sep 10 - Sep 11
includes taxes & fees
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Fully refundable
CA $93
CA $102 total
Sep 14 - Sep 15
includes taxes & fees
7.2/10 Good! (770 reviews)
"Many long black hair extensions throughout the room and duvet cover. Bathroom sink had lots of mildew behind the faucet."
Reviewed on Sep 3, 2026
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.
What to do in Great Diamond Island
Sunset Windjammer Cruise Along the Coast of Portland Maine
CA $107
per adult
90% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
CA $82
per adult
Frequently asked questions
How much does a Great Diamond Island vacation package cost?
Less than you might think — from just CA $861, 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 vacation 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 vacation starts right here, right now!
How far in advance should I book my Great Diamond Island vacation?
Smart travelers 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 organizing 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 vacation 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 vacation 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 vacation 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.
Explore a world of travel with Expedia
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- Flights from Moncton (YQM) to Portland (PWM)
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- Flights from Vancouver (YVR) to Portland (PWM)
- Flights to Great Diamond Island
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- Flights from Edmonton (YEG) to Portland (PWM)
- Flights from Calgary (YYC) to Portland (PWM)
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- Portland Museum of Art
- Gooch's Beach
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- Portland Head Light
- Visit Ferry Village
- Maine Mall
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- Desert of Maine
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- Scarborough Beach State Park
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- Aquaboggan Water Park
- Visit Old Orchard Beach
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- Visit Old Port
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
