Great Diamond Island Vacations from $449
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The Latest Great Diamond Island vacation packages
Price found within the past 48 hours. Click for updated prices.
84 Main
Price was $598, price is now $449 per person
$449
per person
Feb 12 - Feb 16
found 8 hours 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
Save 100% on your flight
Price was $1,461, price is now $1,092 per person
$1,092
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
The room along with the view was spectacular - Beautifully decorated - Clean - Crisp - The Staff - Beyond Helpful!!
The location overlooking the Atlantic Ocean even this time of year with the sun and the ocean waves hitting the rocks was like out of a movie!! Their restaurants 5 star in my opinion!! Just the people they have working looking out for you and making sure you are having an experience of a lifetime!! Thank you again Cliff House - See you very soon!!!
Reviewed on Jan 6, 2026
Portland Harbor Hotel
Downtown Portland
Price was $929, price is now $719 per person
$719
per person
Feb 13 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) 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 Docent’s Collection – Thompson Block
Downtown Portland
Price was $784, price is now $612 per person
$612
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) 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
The McKernan Inn
Price was $751, price is now $594 per person
$594
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) 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
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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
4.5/5(88 reviews)
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
4.5/5(255 reviews)
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 13 to Jan 14
$87 total
Jan 13 - Jan 14
Total with taxes and fees
7.8/10 Good! (1,319 reviews)
Front desk attendant was very pleasant and helpful. Room was clean and well stocked with towels and toiletries.
Reviewed on Jan 5, 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 Jan 27 to Jan 28
$108 total
Jan 27 - Jan 28
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
$125 nightly
The price is $139 total per night from Jan 19 to Jan 20
$139 total
Jan 19 - Jan 20
Total with taxes and fees
9.4/10 Exceptional! (1,567 reviews)
Staff was great. Perfect location to explore the area.
Reviewed on Jan 4, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
