
Great Diamond Island Vacations from $532
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The Latest Great Diamond Island vacation packages
Price found within the past 48 hours. Click for updated prices.

The Docent's Collection
Downtown Portland
Save 100% on your flight
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (219 reviews)
Property is modern and clean and a great choice if staying more than one night. The 5:00 check in time is inconvenient and the additional rates for early check in are ridiculous. Our room was ready early even though the information given before check in stated early check in was not available, so we appreciated that. Bed was okay comfort-wise, but the pillows are awful.
The biggest gripe I had was being woken by a very loud family with screaming kids well before 7:30 am on a day we looked forward to sleeping in. If this matters to you, the walls and floors are not very soundproof. This was a very unpleasant way to start the second day of a two-day trip. On a positive note, the staff was available via text and responded to our questions quickly and professionally. One suggestion-an exterior sign. The loft was hard to find, with only small signage on the entry doors which is not easily visible from the street. Overall we were happy and would stay again.
Reviewed on Aug 11, 2025

The Weldon Hotel
Downtown Portland
Save 100% on your flight
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.8/10 Exceptional! (68 reviews)
We had a great stay in the 2 bedroom unit. great set up and was super clean. Loved the proximity to the shopping area and restaurants. Only issue was the front door lock, noticed a lot of the other people were leaving the lock open. Would stay here again
Reviewed on Jul 24, 2025

Cliff House Maine
Save 100% on your flight
per person
Oct 20 - Oct 23
found 11 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
9.4/10 Exceptional! (1,005 reviews)
We had an amazing stay at Cliffhouse and were pleasantly surprised by how beautiful it is. The only minor issues we encountered were that the pullout couch was quite uncomfortable for our kids, and it was frustrating that children aren’t allowed in the main pool—everyone with kids ends up crowded around a small pool off to the side. Aside from that, everything else was fantastic!
Reviewed on Aug 9, 2025


Portland Harbor Hotel
Downtown Portland
Save 100% on your flight
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.2/10 Wonderful! (1,542 reviews)
The central garden area for drinks and meals was a real positive. We had pre dinner drinks and breakfast coffee there.
Reviewed on Aug 12, 2025
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

Downtown Golden Adventure Quest Experience in Portland
$7
per adult

Afternoon Windjammer Cruise Along the Coast of Portland Maine
$67
per adult

Sunset Lighthouse Cruise Tour from Casco Bay
$56
per adult
90% of travellers recommend
Great Diamond Island Hotel Deals

Days Inn by Wyndham Airport/Maine Mall
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $127 total per night from Aug 24 to Aug 25
$127 total
Aug 24 - Aug 25
Total includes taxes and fees
7.8/10 Good! (1,150 reviews)
"Friendly staff, very quiet. I felt very comfortable with my family there"
Reviewed on Aug 10, 2025

Germaine Inn South Portland
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
$97 nightly
The price is $106 total per night from Aug 24 to Aug 25
$106 total
Aug 24 - Aug 25
Total includes taxes and fees
7.6/10 Good! (126 reviews)
"Very old hotel. No good air because the windows don't open."
Reviewed on Aug 8, 2025

Ramada Plaza by Wyndham Portland
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $147 total per night from Sep 1 to Sep 2
$147 total
Sep 1 - Sep 2
Total includes taxes and fees
7.6/10 Good! (1,043 reviews)
"."
Reviewed on Aug 9, 2025
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.
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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.