Great Diamond Island Vacations from $447
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The Latest Great Diamond Island vacation packages
Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites
Moody
Save 100% on your flight
Price was $679, price is now $447 per person
$447
per person
Sep 5 - Sep 7
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9/10 Wonderful! (1,008 reviews)
The property was beautiful and the staff members were all really kind and helpful!
Reviewed on Jul 11, 2026
Evalina Hotel
Downtown Portland
Save 100% on your flight
Price was $2,983, price is now $1,849 per person
$1,849
per person
Sep 16 - Sep 22
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
10/10 Exceptional! (5 reviews)
It was a spacious, clean, well thought out space with all the expected amenities. The location is ideal, and the hotel is truly a treasure.
Reviewed on Jun 28, 2026
The Meadowmere Resort
Save 100% on your flight
Price was $992, price is now $649 per person
$649
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
Had a great stay. Kind and helpful staff. Will be back!
Reviewed on Jul 11, 2026
Saco Bay Hotel
Save 100% on your flight
Price was $924, price is now $638 per person
$638
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
7.6/10 Good! (1,081 reviews)
We arrived during a holiday weekend and were disappointed by the overall condition of the hotel. The common areas were very dirty and had a strong, unpleasant odor throughout.
Our room also fell below expectations. We found sand under the duvet on the bed, which raised concerns about the cleanliness of the linens, and the lamp shades were covered in stains.
The pool area was also poorly maintained. Several lounge chairs were broken, and there were bugs in the pool, making it uninviting and difficult to enjoy.
Lastly, the walls are very thin you can hear everything in the room next door.
Overall, the level of cleanliness and maintenance did not meet the standard we expected for our stay.
Reviewed on Jul 8, 2026
Inn By The Sea
Save 100% on your flight
Price was $2,443, price is now $1,734 per person
$1,734
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (323 reviews)
We just love it there. It is our happy place. Beautiful grounds, comfortable, friendly and downy to earth staff. Wonderful place!
Reviewed on Jun 26, 2026
Don't see what you're looking for?
See all available trips from Columbus to Great Diamond Island
View all tripsWhat to do in Great Diamond Island
Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour
$79
per adult
100% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
$77
per adult
88% of travellers recommend
Great Diamond Island Hotel Deals
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
$135 nightly
The price is $150 total per night from Jul 19 to Jul 20
$150 total
Jul 19 - Jul 20
Total with taxes and fees
8.2/10 Very Good! (1,547 reviews)
"Wonderful stay. The pool and hot tub were a major plus guest services on point!! My airport transport was not honored when we left. That's okay. I found another way to make it back. Very comfortable beds. Super clean. Bathrooms were lovely with plenty of towels and amenities."
Reviewed on Jul 11, 2026
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
340 Park Ave Portland ME
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $176 total per night from Jul 12 to Jul 13
$176 total
Jul 12 - Jul 13
Total with taxes and fees
8.6/10 Excellent! (2,198 reviews)
"This is my second stay at La Quinta in Portland. It is a very well maintained and managed hotel. It is quiet, in good condition, and consistently clean. The staff is very pleasant and helpful; and the location is convenient."
Reviewed on Jul 11, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
$266 nightly
The price is $294 total per night from Jul 12 to Jul 13
$294 total
Jul 12 - Jul 13
Total with taxes and fees
9.4/10 Exceptional! (1,262 reviews)
"First of all, the hotel front desk and staff were excellent. Very friendly and very helpful. The most disappointing part of the stay was paying $12 for a single shot of vodka and $5.50 for a small drip coffee. Seemed out of place at a Cambria hotel in Portland Maine."
Reviewed on Jul 10, 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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- Fort Preble
- Charles Q. Clapp House
- Maine Jewish Museum
- Portland Museum of Art
- Eastern Promenade
- Visit Portland
- State Theatre
- Casco Bay Lines Ferry Terminal
- Visit Old Port
- Maine College of Art
- Victoria Mansion
- Downtown Portland Vacations
- Fort Williams Park
- Southern Maine Community College
- Umbrella Cover Museum
- Mackworth Island State Park
- South Portland Vacations
- Old Port Vacations
- Maine Sports Hall of Fame
- Peaks Island Vacations
- Ll Bean Flagship Store
- Visit Bailey Island
- Portland Head Light
- Merrill Auditorium
- Two Lights State Park
- Goddard Mansion
- East End Beach
- Spring Point Ledge Lighthouse
- International Cryptozoology Museum
- Higgins Beach
- Wadsworth-Longfellow House
- State Street Church
- Bug Light
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
