Great Diamond Island Vacations from $621
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The Latest Great Diamond Island vacation packages
Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites
Moody
$621
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9/10 Wonderful! (1,011 reviews)
Nice facility with great views out the rear facing rooms. If you like to kayak and the tide is in you can rent one and go right from the back of the property .
Reviewed on Aug 25, 2026
Blind Tiger Portland - Danforth Street.
West End
$1,675
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (189 reviews)
Perfect location & beautiful stay! Very unique property. Great recommendations & lovely hospitality. We will definitely come back the next time we’re in Portland!
:)
Reviewed on Aug 23, 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 Explorer: Boat Cruise with Oysters & Prosecco
$137
per adult
Great Diamond Island Hotel Deals
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Fully refundable
$76 nightly
$83 total
Aug 30 - Aug 31
Total with taxes and fees
7.2/10 Good! (729 reviews)
"i understand that the room charge was not much, but there were unsafisfactory conditions below. Shower head was dirty. Coffee maker was not cleaned.(water left in the tank). Shampoo holder had stain. Wifi was interrupted every 10 seconds. Even considering the cost of the room charge, I would not ..."
Reviewed on Aug 25, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
$118 nightly
$131 total
Sep 1 - Sep 2
Total with taxes and fees
8/10 Very Good! (1,644 reviews)
"The property could use some modern renovations. The elevator was a bit slow and sketchy. I was happy to have access to a shuttle because it saved money from Uber rides. The hotel was clean and the staff was friendly and accommodating. Thank-you!"
Reviewed on Aug 25, 2026
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
$78 nightly
$85 total
Sep 1 - Sep 2
Total with taxes and fees
6.4/10 (1,088 reviews)
"Needs maintenance but still good"
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.
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.