Great Diamond Island Vacations from $226
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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
Price was $318, price is now $226 per person
$226
per person
Mar 18 - Mar 20
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Reduce noise from patrons near elevator and coffee area on second floor, very loud
Reviewed on Jan 10, 2026
The McKernan Inn
Price was $908, price is now $627 per person
$627
per person
Apr 2 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9/10 Wonderful! (83 reviews)
Gorgeous grounds and venue with a beautiful oceanfront view. Plenty of parking as part of SMCC campus. Short drive to downtown Portland and lots of stores around in South Portland. Very unique experience, would stay again without hesitation!
Reviewed on Dec 27, 2025
84 Main
Price was $598, price is now $449 per person
$449
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
10/10 Exceptional! (52 reviews)
This property was absolutely beautiful and well maintained! Right in the heart of Kennebunk within walking distance to great restaurants!!
Reviewed on Oct 26, 2025
Cliff House Maine
Bald Head
Price was $1,778, price is now $1,378 per person
$1,378
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
Loved the hotel had a great time with a group of friends
Reviewed on Jan 12, 2026
The Docent’s Collection – Thompson Block
Downtown Portland
Price was $369, price is now $288 per person
$288
per person
Mar 18 - Mar 20
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
Room and amenities were great and ease of access to both the room and surrounding businesses is ideal.
Reviewed on Jan 10, 2026
Don't see what you're looking for?
See all available trips from Columbus to Great Diamond Island
View all tripsDiscover the most popular places to visit in Great Diamond Island
State Theatre
The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.
Portland Museum of Art
Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.
East End Beach
Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.
What to do in Great Diamond Island
Portland Smartphone Audio Tour: Self-Guided Drive
$15
per traveler
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
$10
per traveler
Ultimate Portland Self-Guided Driving GPS Audio Tour
$17
per traveler
100% of travellers recommend
Great Diamond Island Hotel Deals
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
$78 nightly
The price is $87 total per night from Jan 15 to Jan 16
$87 total
Jan 15 - Jan 16
Total with taxes and fees
8/10 Very Good! (1,322 reviews)
Very nice
Reviewed on Jan 11, 2026
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $108 total per night from Feb 8 to Feb 9
$108 total
Feb 8 - Feb 9
Total with taxes and fees
8.8/10 Excellent! (1,008 reviews)
Room was clean and had all amenities.
Reviewed on Jan 6, 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $152 total per night from Jan 25 to Jan 26
$152 total
Jan 25 - Jan 26
Total with taxes and fees
9.4/10 Exceptional! (1,573 reviews)
Room is awesome , love the hotel.
Reviewed on Jan 12, 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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- Visit Old Port
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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.
