Great Diamond Island Vacations from $590
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The Latest Great Diamond Island vacation packages
Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
Downtown Portland
$590
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.2/10 Wonderful! (1,864 reviews)
There was no in room mini bar, so it was challenging to spend the $35 per day mandatory food/beverage charge. The sound proofing between rooms with adjoining doors was not great. Could clearly hear every word of conversation. If you’re looking for a very nice boutique hotel, this probably isn’t your place.
Reviewed on Oct 10, 2026
Blind Tiger Portland - Danforth Street.
West End
$813
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (193 reviews)
Adorable stylish house and spacious room comfortable bed. Worth the walk to old port. Will come back!
Reviewed on Oct 6, 2026
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View all tripsWhat to do in Great Diamond Island
Sunset Windjammer Cruise Along the Coast of Portland Maine
$77
per adult
90% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
$59
per adult
80% of travellers recommend
Great Diamond Island Hotel Deals
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
$83 nightly
$92 total
Nov 1 - Nov 2
Total with taxes and fees
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$135 nightly
$149 total
Nov 1 - Nov 2
Total with taxes and fees
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
$88 nightly
$97 total
Oct 25 - Oct 26
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
"Great"
Reviewed on Oct 10, 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.
Find the Best Great Diamond Island Vacation Packages
Great Diamond Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
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- Fort Preble
- Charles Q. Clapp House
- Maine Jewish Museum
- Portland Museum of Art
- Eastern Promenade
- Visit Portland
- State Theatre
- Casco Bay Lines Ferry Terminal
- Visit Old Port
- Maine College of Art
- Victoria Mansion
- Downtown Portland Vacations
- Fort Williams Park
- Southern Maine Community College
- Umbrella Cover Museum
- Mackworth Island State Park
- South Portland Vacations
- Old Port Vacations
- Maine Sports Hall of Fame
- Peaks Island Vacations
- Ll Bean Flagship Store
- Visit Bailey Island
- Portland Head Light
- Merrill Auditorium
- Two Lights State Park
- Goddard Mansion
- East End Beach
- Spring Point Ledge Lighthouse
- International Cryptozoology Museum
- Higgins Beach
- Wadsworth-Longfellow House
- State Street Church
- Bug Light
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
