Great Diamond Island Vacation Packages
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Top Great Diamond Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Inn at Diamond Cove
per person
Sep 12 - Sep 15
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (177 reviews)
We had an amazing stay! What a gem of an experience - all of the staff was wonderful - Antonio at the lobby cafe was so kind and friendly and Kayla at concierge always went above and beyond!!
Reviewed on Jul. 20, 2025
Cliff House Maine
per person
Sep 4 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.4/10 Exceptional! (1,008 reviews)
Beautiful property with great service and dining options. Rooms were spacious with nautical decor. Pool was beautiful but get there early if you want a lounge with umbrella!
Reviewed on Jul. 30, 2025
The Docent's Collection
Downtown Portland
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.6/10 Exceptional! (211 reviews)
Fantastic place to stay when visiting Portland. The location can't be beat -- within a couple of blocks to the ferry terminal and Old Town shops and restaurants. The building is next to a police station and my family and I felt very safe. The unit was immaculate, modern, and fully equipped. Onsite parking was a huge bonus, as was the friendly and helpful staff. I would, without hesitation, stay at The Docent's Collection again.
Reviewed on Jul. 31, 2025
Portland Harbor Hotel
Downtown Portland
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.2/10 Wonderful! (1,523 reviews)
We really enjoyed our stay. Great location, staff couldn’t have been more friendly, and a clean comfortable room. Snacks and a Keurig in the hall for all on the floor to share was nice, although there was something wrong with the Keurig. (It worked, but there were multiple times I had to run it twice.)
Reviewed on Jul. 31, 2025
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
The price is CA $152 per night from Aug 24 to Aug 25
CA $152
CA $166 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,101 reviews)
"Outside wasn't well kept up. The room was average, clean."
Reviewed on Jul. 31, 2025
Clarion Hotel Portland
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $211 per night from Aug 11 to Aug 12
CA $211
CA $234 total
Aug 11 - Aug 12
includes taxes & fees
7.8/10 Good! (1,038 reviews)
"The lobby is welcoming. I mean spacious, clean and bright!"
Reviewed on Jul. 30, 2025
Comfort Inn Airport
90 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Sep 1 to Sep 2
CA $186
CA $203 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (1,430 reviews)
"Property was dated especially in the entrance, not well lit. But the room was great and I slept so well in that bed, great mattress and pillows ."
Reviewed on Jul. 30, 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.
Discover the most popular places to visit in Great Diamond Island
State Theatre
4.5/5(5 reviews)
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
5/5(5 reviews)
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 Lighthouses Sightseeing Cruise with Drinks
CA $95
per adult
Portland: Sightseeing Cruise to Portland Head Light
CA $49
per adult
98% of travellers recommend
Frequently asked questions
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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.