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
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Top Great Diamond Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites
Moody
CA $1,034
per person
Oct 2 - Oct 5
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,011 reviews)
Very pleasant stay. The staff was simply amazing. Everyone we came in contact with was exceptionally friendly and helpful.
The hotel is a bit of a hike from Ogunquit, but only 10 minutes from the beach. There are trolleys to take you into Ogunquit or it’s a 10 minute drive. If you don’t need to be in the middle of the action and want a nice hotel with a lovely staff, book it!
Reviewed on Aug 23, 2026
Portland Harbor Hotel
Downtown Portland
CA $1,183
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Portland (PWM)
9.2/10 Wonderful! (1,791 reviews)
We arrived early and they could not check us in until 4pm. The snacks were all gone in lobby and we could not use restaurant or room service due to a wedding. The band in the courtyard kept us up in the late evening. We travel extensively and this was not a good experience.
Reviewed on Aug 24, 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 $99
CA $108 total
Aug 31 - Sep 1
includes taxes & fees
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
CA $163
CA $180 total
Sep 7 - Sep 8
includes taxes & fees
8/10 Very good! (1,640 reviews)
"Really a pleasant place to stay. And a great price!"
Reviewed on Aug 23, 2026
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
CA $108
CA $118 total
Sep 3 - Sep 4
includes taxes & fees
6.4/10 (1,086 reviews)
"Great place and breakfast was amazing especially when you can make your own waffle"
Reviewed on Aug 24, 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 $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 $944, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
