Great Diamond Island Vacations from $827
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The Latest Great Diamond Island vacation packages
Price found within the past 48 hours. Click for updated prices.
Nautical Mile
Price was $995, price is now $827 per person
$827
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
8.6/10 Excellent! (25 reviews)
I've stayed at the Nautical Mile many times! The rooms are perfect for a get-away! The pool is always ready to cool off in and the people, both working at the Nautical Mile and guests are very friendly.
Reviewed on Sep 8, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was $1,034, price is now $862 per person
$862
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Portland (PWM)
9.6/10 Exceptional! (419 reviews)
We loved everything. The only thing is the mattress is a little soft and you easily roll to the middle!
Reviewed on Oct 27, 2026
The Meadowmere Resort
Price was $1,136, price is now $954 per person
$954
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
8.6/10 Excellent! (1,007 reviews)
The property was very clean and well maintained. The staff were friendly and helpful. It’s the ideal location when attending the Ogunquit Playhouse. We didn’t have time to take advantage of them, but I was impressed by the many amenities available. The complimentary breakfast was adequate.
Reviewed on Oct 26, 2026
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See all available trips from Columbus to Great Diamond Island
View all tripsWhat to do in Great Diamond Island
Sunset Windjammer Cruise Along the Coast of Portland Maine
$77
per adult
92% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
$59
per adult
80% of travellers recommend
Great Diamond Island Hotel Deals
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $119 total per night from Nov 18 to Nov 19
$119 total
Nov 18 - Nov 19
Total with taxes and fees
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
$83 nightly
The price is $92 total per night from Nov 3 to Nov 4
$92 total
Nov 3 - Nov 4
Total with taxes and fees
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
$72 nightly
The price is $79 total per night from Nov 11 to Nov 12
$79 total
Nov 11 - Nov 12
Total with taxes and 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.
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.
