
Great Diamond Island Vacations from $292
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The Latest Great Diamond Island vacation packages
Price found within the past 48 hours. Click for updated prices.

Dormir
Price was $328, price is now $292 per person
$292
per person
Dec 28 - Dec 30
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
8.8/10 Excellent! (1,005 reviews)
Great hotel, I am glad I picked them. The room was comfortable and updated. Rooms do include a refrigerator and microwave.
Reviewed on Nov 5, 2025

Blind Tiger Portland - Danforth Street.
West End
Price was $837, price is now $682 per person
$682
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
9.6/10 Exceptional! (155 reviews)
Wish they had a liquor license and could do a cocktail hour in addition to a breakfast service. Wish they had just a tad more breakfast options. Really wish they had a key pad and front door access! LOVED the fire places in every room. Property manager was lovely and friendly. Loved the snacks available and variety.
Reviewed on Oct 27, 2025

84 Main
Price was $754, price is now $634 per person
$634
per person
Dec 19 - Dec 22
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
10/10 Exceptional! (51 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

Waldo Emerson Inn
Price was $913, price is now $799 per person
$799
per person
Dec 19 - Dec 22
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
8.8/10 Excellent! (334 reviews)
This inn was so charming! Upon arrival, there were complimentary cookies and apple cider waiting for us. Amelia and Ron were so friendly and accommodating to ensure we had an amazing stay. Rooms were spotless and very comfortable.
Reviewed on Oct 28, 2025

AWOL Kennebunkport
Price was $989, price is now $901 per person
$901
per person
Dec 19 - Dec 22
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (215 reviews)
Great staff and facilities. Loved the room and the hotel as a whole. Walking distance into the town.
Would highly recommend this place, one of my favourite hotel experiences in recent years.
Reviewed on Nov 4, 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
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

Portland, Maine: Hidden Histories Guided Walking Tour
$49
per adult

Portland Smartphone Audio Tour: Self-Guided Drive
$17
per traveler
Great Diamond Island Hotel Deals

Portland Harbor Hotel
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
$170 nightly
The price is $188 total per night from Nov 16 to Nov 17
$188 total
Nov 16 - Nov 17
Total with taxes and fees
9.2/10 Wonderful! (1,685 reviews)
Great service
Reviewed on Nov 6, 2025

Clarion Hotel Portland
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $92 total per night from Nov 11 to Nov 12
$92 total
Nov 11 - Nov 12
Total with taxes and fees
7.8/10 Good! (1,218 reviews)
It was clean and quiet-what I needed!
Reviewed on Nov 3, 2025

Tru by Hilton Portland Airport Area
369 Maine Mall Road, South Portland, ME
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $86 total per night from Nov 13 to Nov 14
$86 total
Nov 13 - Nov 14
Total with taxes and fees
8.8/10 Excellent! (1,591 reviews)
All was as expected from Tru experiences.
Reviewed on Nov 4, 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.
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.



















