
Great Diamond Island Vacations from $526
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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
Price was $751, price is now $526 per person
$526
per person
Oct 27 - Oct 30
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (226 reviews)
Very modern and new condition. Digital key worked pretty well and convenient. Lots of good restaurants within walking distance. We enjoyed our stay.
Reviewed on Aug 25, 2025

The Weldon Hotel
Downtown Portland
Save 100% on your flight
Price was $986, price is now $652 per person
$652
per person
Oct 27 - Oct 30
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.8/10 Exceptional! (68 reviews)
it was difficult dropping off luggage for them to hold on to before and after checkin because there's no front desk and the don't pick up the phone right away
Reviewed on Aug 25, 2025

Cliff House Maine
Price was $1,267, price is now $909 per person
$909
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (1,002 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


InnSeason Resorts The Falls at Ogunquit
Save 100% on your flight
Price was $1,158, price is now $889 per person
$889
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (344 reviews)
Clean comfortable rooms. Nice amenities, walking distance to the beach and restaurants. Short drive or shuttle to downtown area.
We would return and recommend this place.
Reviewed on Aug 16, 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
$59
per adult
90% of travellers recommend
Great Diamond Island Hotel Deals

Clarion Hotel Portland
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $168 total per night from Sep 2 to Sep 3
$168 total
Sep 2 - Sep 3
Total with taxes and fees
7.8/10 Good! (1,010 reviews)
"Consistent- we’ve chosen to stay many times both when we need Park and Fly and when going to local concerts at Thompson Point so we can walk over, and have the long drive home late at night. Clean, friendly and convenient. Price is reasonable."
Reviewed on Aug 23, 2025

Days Inn by Wyndham Airport/Maine Mall
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $117 total per night from Aug 26 to Aug 27
$117 total
Aug 26 - Aug 27
Total with taxes and fees
7.8/10 Good! (1,223 reviews)
Excellent choice for single night stay
"Very convenient hotel for those flying into PWM. Quick stop on the way to Rockland. Front desk was pleasant. Got me toothpaste I forgot. Told them about stopped up sink and they noted it. (It wasn't an issue for me as I simply removed the stopper and left it on the counter to be cleaned.) Breakfast ..."
Reviewed on Aug 22, 2025

Germaine Inn South Portland
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
$95 nightly
The price is $103 total per night from Sep 7 to Sep 8
$103 total
Sep 7 - Sep 8
Total with taxes and fees
7.2/10 Good! (175 reviews)
"My check in was fantastic.. My check out took way too long."
Reviewed on Aug 23, 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.