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Top Great Diamond Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Airport/Maine Mall
per person
Aug. 22 - Aug. 29
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
7.8/10 Good! (1,003 reviews)
Very nice room. Comfortable bed. Only downside of the whole trip was that I hadn't traveled to that area in a few years and managed to take a wrong turn, adding about a half hour to my driving time. Once I found it, everything was fine! Location was near just about everything I was there to do, so I was very pleased!
Reviewed on Jun. 17, 2024
Canopy by Hilton Portland Waterfront
Downtown Portland
Save 100% on your flight
per person
Aug. 22 - Aug. 29
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (670 reviews)
We loved the people and the decor/layout of the hotel, and its rooms. The location was perfect for us. We enjoyed both the rooftop bar and downstairs restuarant/coffee area. The only negative for us was the $40 parking fee per night. Service by the valets was excellent, however.
Reviewed on Jun. 17, 2024
Ocean Gate Resort
per person
Aug. 15 - Aug. 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8.6/10 Excellent! (991 reviews)
We paid extra for an ocean front room. Our view was very different from the pictures- it was mostly blocked by trees so our balcony was not worth using. Views from other parts of the property were much better. We were given a handicap accessible room so our bathroom was huge and room was much smaller. Overall just not a great experience. Office smelled like cigarettes.
Reviewed on Oct. 3, 2023
Great Diamond Island Hotel Deals
Casco Bay Hotel, Ascend Hotel Collection
80 John Roberts Rd., South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Jun. 23 to Jun. 24
CA $159
CA $174 total
includes taxes & fees
Jun 23 - Jun 24
8.4/10 Very Good! (1,607 reviews)
"Good solid stay close to hospital for 2 night layover. Clean, pleasant, friendly."
Reviewed on Jun. 15, 2024
The Westin Portland Harborview
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $372 per night from Jun. 24 to Jun. 25
CA $372
CA $423 total
includes taxes & fees
Jun 24 - Jun 25
8.4/10 Very Good! (1,050 reviews)
"All the staff were so helpful and kind."
Reviewed on Jun. 16, 2024
Portland Harbor Hotel
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $399 per night from Jul. 2 to Jul. 3
CA $399
CA $493 total
includes taxes & fees
Jul 2 - Jul 3
9/10 Wonderful! (1,208 reviews)
"Good location and walkable."
Reviewed on Jun. 17, 2024
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.
Frequently asked questions
Discover the most popular places to visit in Great Diamond Island
LL Bean Flagship Store
4.5/5(50 reviews)
During your trip to Freeport, you can enjoy retail therapy at LL Bean Flagship Store. Stroll along the area's waterfront or simply enjoy its seafood restaurants.
Higgins Beach
4.5/5(8 reviews)
At the mouth of the Spurwink River in Scarborough, take a stroll on the white sand or paddle a kayak over gentle waves.
Portland Head Light
4.5/5(27 reviews)
Look out across the Atlantic Ocean from Portland’s iconic white lighthouse, which has presided over the southern Maine coastline since the 18th century.
What to do in Great Diamond Island
Portland: Old Port Seafood Lovers Tour
CA $198
Per adult
Sunset Lighthouse Harbor Cruise from Portland's Old Port
CA $122
Per adult
Portland, Maine: Old Port Brewery & Pub Walking Tour
CA $121
Per adult
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Packages
General
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.