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.
Ogunquit River Inn & Suites
Moody
CA $1,539
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9/10 Wonderful! (1,017 reviews)
This is not a property I could recommend for anyone. The bathroom and room did not have any place to hang clothes or towels! I found this extremely difficult especially on the OCEAN! I used the ironing board to hang our clothes from! The only 2 ice machines were on a different level and very far from our room. The pool was even worse. It was down a steep hill and the material surrounding the pool was extremely rough under the feet. In the back of the property there were many Canadian Geese (they are not friendly) and there was no fence to keep them out. So, they drove us out of the 2 chairs that were there and we had to avoid their feces which covered the lawn area. The breakfast was not very kid friendly or anyone with allergies.
Reviewed on Aug 13, 2026
River View Resort
CA $1,700
per person
Oct 23 - Oct 30
found 1 hour ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9/10 Wonderful! (332 reviews)
The room was clean (but a bit dated), and comfortable. Staff was welcoming and very friendly. It was perfect to stay w/ my mother and teen-aged son. It was nice to have a full kitchen, and conveniently supplied with the essentials. We would stay there again!
Reviewed on Aug 4, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
CA $2,697
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (367 reviews)
Parking was tricky. It was not as close to the water as anticipated.
Reviewed on Aug 14, 2026
Ready to book your vacation to Great Diamond Island?
Great Diamond Island Hotel Deals
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Fully refundable
CA $129
CA $141 total
Sep 13 - Sep 14
includes taxes & fees
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
CA $182
CA $202 total
Sep 1 - Sep 2
includes taxes & fees
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
CA $133
CA $145 total
Sep 14 - Sep 15
includes taxes & fees
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 $109
per adult
90% of travellers recommend
Morning Lighthouse Cruise Along the Coast of Portland Maine
CA $83
per adult
Frequently asked questions
How much does a Great Diamond Island vacation package cost?
Less than you might think — from just CA $1,539, 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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- Portland Museum of Art
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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.
