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.
The Docent's Collection at 121 Middle Street
Downtown Portland
CA $1,617
per person
Oct 23 - Oct 25
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
9.6/10 Exceptional! (382 reviews)
Glad to discover this newer place to stay. Loved the full apartment.
Reviewed on Sep 12, 2026
The Docent's Collection at 178 Middle Street
Downtown Portland
CA $1,542
per person
Oct 23 - Oct 25
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
9.6/10 Exceptional! (61 reviews)
Room was beautiful, new, and clean. Staff upon check in was extremely helpful and courteous, Excellent accommodations. Close to many sights, bars, and restaurants. Would stay again in a heartbeat.
Reviewed on Sep 12, 2026
Ready to book your vacation to Great Diamond Island?
Great Diamond Island Hotel Deals
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Fully refundable
CA $198
CA $216 total
Sep 27 - Sep 28
includes taxes & fees
8.4/10 Very good! (3,014 reviews)
"Overall excellent experience for an affordable hotel"
Reviewed on Sep 12, 2026
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
CA $125
CA $136 total
Sep 15 - Sep 16
includes taxes & fees
6.4/10 (1,122 reviews)
"The staff was friendly and let us check in about an hour early. However the hotel is sorely in need of a good cleaning as well as paint to refresh and actual repairs to the property. If I had other choices I would not return for those reasons."
Reviewed on Sep 13, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
CA $159
CA $176 total
Sep 20 - Sep 21
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 $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 $502, 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.
