Great Diamond Island Vacations from $596
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The Latest Great Diamond Island vacation packages
Price found within the past 48 hours. Click for updated prices.
River View Resort
Save 100% on your flight
Price was $901, price is now $596 per person
$596
per person
Jul 23 - Jul 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9/10 Wonderful! (323 reviews)
Clean room. Space for everyone, pool was nice, staff was friendly. Perfect for our last minute ski trip.
Reviewed on Apr 12, 2026
Hilton Garden Inn Portland Downtown Waterfront
Downtown Portland
Save 100% on your flight
Price was $1,863, price is now $1,337 per person
$1,337
per person
Jun 3 - Jun 8
found 10 hours ago
Roundtrip flight included
Charlotte (CLT) to Portland (PWM)
9.4/10 Exceptional! (1,004 reviews)
The breakfast was hot and fresh each day and the staff was exceptional! We love visiting the Portland Maine location, wonderful views and the entire staff qas welcoming and extreme helpful.
Reviewed on Apr 28, 2026
Hampton Inn Oxford
Save 100% on your flight
Price was $838, price is now $620 per person
$620
per person
Jul 23 - Jul 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9/10 Wonderful! (1,001 reviews)
The room was nice. Easy check in and out.
Reviewed on Apr 10, 2026
Comfort Inn & Suites Scarborough - Portland
Price was $1,165, price is now $891 per person
$891
per person
Jul 14 - Jul 21
found 9 hours ago
Roundtrip flight included
Charlotte (CLT) to Portland (PWM)
7/10 Good! (870 reviews)
I chose this listing because of the late checkout and they told me at front desk they don't have late checkout. The waffle batter dispenser was busted and there was batter all over the counter the first morning and they ran out the second morning. They don't want you to take food out of breakfast area but there is not enough seats and people are down there coughing and sick. The staff is kind and these guys are trying as best they can but incorrect listings are creating a problem.i did not get what I selected or paid for.
Reviewed on Apr 25, 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.
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
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$212 nightly
The price is $235 total per night from May 3 to May 4
$235 total
May 3 - May 4
Total with taxes and fees
9.2/10 Wonderful! (1,754 reviews)
Highly recommended! Very clean and staff were amazing!!
Reviewed on Apr 28, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
$163 nightly
The price is $181 total per night from May 3 to May 4
$181 total
May 3 - May 4
Total with taxes and fees
9.4/10 Exceptional! (1,199 reviews)
Reception was very helpful.
Reviewed on Apr 28, 2026
HomeAwhile
205 Southborough Drive Scarborough ME
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $127 total per night from May 21 to May 22
$127 total
May 21 - May 22
Total with taxes and fees
9.6/10 Exceptional! (27 reviews)
Air conditioning system was making loud clap every 10 minutes, not restful sleep. We arrived late at night, so unfortunately, did not notice right away. We reserved two rooms via Expedia. Upon arrival we were told we have only one room reserved. At the end, hotel was able to find another room for ...
Reviewed on Apr 26, 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.