Great Diamond Island Vacations from $703
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The Latest Great Diamond Island vacation packages
Price found within the past 48 hours. Click for updated prices.
Nautical Mile
$703
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) 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
Blind Tiger Portland - Danforth Street.
West End
$1,094
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (193 reviews)
Wonderful staff, convenient location, fun stay in an old building. So much character with modern amenities and a neighborhood feel. We thoroughly enjoyed our stay and will return. Off-street parking was a huge bonus and the light breakfast had a wide spread. Such a wonderful property.
Reviewed on Oct 11, 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
8.2/10 Very Good! (1,765 reviews)
"Good hotel for the price and amenities. It's a bit aged but I saw they are undergoing new management and renovations in 2027. The complimentary shuttle was really great. Took us back and forth to old port saving us money. They even allowed my pup on the shuttle. Super super close to the Amtrak station. ..."
Reviewed on Oct 11, 2026
The Westin Portland Harborview
157 High St Portland ME
$127 nightly
$141 total
Nov 11 - Nov 12
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 26 - Oct 27
Total with taxes and fees
8.2/10 Very Good! (1,008 reviews)
"The first room they had us in smelled of cigarettes… the entire property is run down. Pay more money and go somewhere else!"
Reviewed on Oct 11, 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.
