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 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
Portland Harbor Hotel
Downtown Portland
CA $1,476
per person
Nov 4 - Nov 11
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,828 reviews)
Nice hotel. Room was comfortable. $35 dollar a day amenity charge that was unexpected-use in restaurant. $45 dollar a day valet parking in attached garage. Elevator slow and needs cleaning. Good location to seafront restaurants.
Reviewed on Sep 2, 2026
Inn By The Sea
CA $2,195
per person
Nov 4 - Nov 11
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (328 reviews)
Lovely property. Very well maintained and taken care of. The option of pool or beach is a plus. Although we didn’t utilize the activities available each day.. it seemed very family friendly. Definitely will be back but hopefully reserve a bigger room or suite. Charming outdoor seating on the huge lawn but mostly in the sun. An indoor lobby with some comfy seating would be great.
Reviewed on Aug 13, 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 $112
CA $122 total
Sep 7 - Sep 8
includes taxes & fees
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Fully refundable
CA $156
CA $170 total
Sep 9 - Sep 10
includes taxes & fees
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Fully refundable
CA $93
CA $101 total
Sep 15 - Sep 16
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 $871, 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.
