Great Diamond Island Vacations from $805
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The Latest Great Diamond Island vacation packages
Price found within the past 48 hours. Click for updated prices.
Newagen Seaside Inn
Save 100% on your flight
Price was $1,219, price is now $805 per person
$805
per person
Aug 2 - Aug 6
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.4/10 Exceptional! (341 reviews)
IT WAS CHARMING AND BEAUTIFUL. The restaurant was wonderful, all the staff was first class, would love to go back.
Reviewed on Oct 14, 2025
Ogunquit River Inn & Suites
Price was $1,936, price is now $1,165 per person
$1,165
per person
Jul 30 - Aug 4
just found
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9/10 Wonderful! (1,003 reviews)
The room was exceptionally clean and comfortable, including the bed.
The staff at reception were amazing, very friendly, helpful and welcoming.parking was easy and accessible.
The dining area was amazing. Unfortunately, breakfast was underwhelming. We understood that it was a continental breakfast but this was not great. Prepackaged muffins and danish, boxed juices… coffee was good. We ate out s few miles away, place specializes in Benedicts, worth the five miles drive!
Lack luster would not keep me from going back.
Reviewed on May 24, 2026
The Weldon Hotel
Downtown Portland
Save 100% on your flight
Price was $2,168, price is now $1,461 per person
$1,461
per person
Jul 8 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Lovely suite! Comfy king bed, everything spotless,
Great location. Would stay here again
Reviewed on Apr 23, 2026
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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(258 reviews)
Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.
University of Southern Maine
4/5(102 reviews)
Explore the campus of University of Southern Maine during your stay in Portland. Stroll along the seaside or attend a sporting event in the area.
Great Diamond Island Hotel Deals
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$263 nightly
The price is $292 total per night from May 26 to May 27
$292 total
May 26 - May 27
Total with taxes and fees
9.4/10 Exceptional! (1,768 reviews)
"An attractive city hotel with contemporary rooms and a lux feeling lobby area. Ed and pillow were very good; a/c was robust. Downside: The one working elevator to the guest rooms made transit up and downstairs slow."
Reviewed on May 25, 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
$158 nightly
The price is $175 total per night from May 26 to May 27
$175 total
May 26 - May 27
Total with taxes and fees
9.4/10 Exceptional! (1,650 reviews)
"Just okay, guest services staff a bit aloof. Can’t beat the location in the heart of the old port. Comfortable bed. Room service closed too early. Nothing in the minibar fridge. Walls are surprisingly thin. I expected more from the Regency."
Reviewed on May 25, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundableReserve now, pay when you stay
$204 nightly
The price is $225 total per night from May 26 to May 27
$225 total
May 26 - May 27
Total with taxes and fees
9.4/10 Exceptional! (1,219 reviews)
"Clean room, nice location. Wish the tv was a smart tv, and found the $25/room sort of annoying since the restaurant on property was understaffed. But overall we enjoyed it."
Reviewed on May 21, 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.