Great Diamond Island Cheap Vacations
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Flight and Cheap hotel deals in Great Diamond Island
Price found within the past 48 hours. Click for updated prices.
Canopy by Hilton Portland Waterfront
Downtown Portland
Price was CA $2,451, price is now CA $2,187 per person
CA $2,187
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
The breakfast on Mother’s Day was amazing. We loved the Luna rooftop. The staff and bartenders were top notch. The hotel was very well kept. Definitely will be back.
Reviewed on May 11, 2026
White Barn Inn & Spa, Auberge Collection
Price was CA $5,398, price is now CA $4,844 per person
CA $4,844
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.4/10 Exceptional! (114 reviews)
The White Barn Inn was first class from check in to check out! It has the wow factor we love - complimentary valet parking, welcome cocktails, basket of treats waiting in our room, coffee & pastry delivered to our door at our preferred time each morning, turn down service, incredible staff, delicious restaurant, and perfect location. We will definitely return!
Reviewed on May 12, 2026
Grasshopper Inn
Price was CA $1,831, price is now CA $1,656 per person
CA $1,656
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.8/10 Exceptional! (71 reviews)
We had a fantastic stay at Grasshopper Inn and will definitely return when back in the area. Clean, friendly staff and brilliant location.
Reviewed on Oct 22, 2025
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Price found within the past 48 hours. Click for updated prices.
White Barn Inn & Spa, Auberge Collection
Price was CA $5,398, price is now CA $4,844 per person
CA $4,844
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.4/10 Exceptional! (114 reviews)
The White Barn Inn was first class from check in to check out! It has the wow factor we love - complimentary valet parking, welcome cocktails, basket of treats waiting in our room, coffee & pastry delivered to our door at our preferred time each morning, turn down service, incredible staff, delicious restaurant, and perfect location. We will definitely return!
Reviewed on May 12, 2026
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View all trips3 Night Cheap holidays in Great Diamond Island
Price found within the past 48 hours. Click for updated prices.
Canopy by Hilton Portland Waterfront
Downtown Portland
Price was CA $1,611, price is now CA $1,509 per person
CA $1,509
per person
Jun 20 - Jun 23
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
The breakfast on Mother’s Day was amazing. We loved the Luna rooftop. The staff and bartenders were top notch. The hotel was very well kept. Definitely will be back.
Reviewed on May 11, 2026
Breakwater Inn
Price was CA $1,299, price is now CA $1,296 per person
CA $1,296
per person
Jun 20 - Jun 23
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.4/10 Very Good! (57 reviews)
Hotel is in the middle of a remodel. Was supposed to have queen bed got a full. Other than that room was remodled nicely.
Pillows weren't the greatest. No complimentary breakfast as was mentioned
when booking. AC/ Heating very loud.When the remodel is finished it will be a nice little place to stay for a weekend.
Reviewed on Apr 19, 2026
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Price found within the past 48 hours. Click for updated prices.
Saco Bay Hotel
Price was CA $1,432, price is now CA $1,210 per person
CA $1,210
per person
Jun 17 - Jun 21
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
7.6/10 Good! (1,049 reviews)
The internet was not secure
The room did not have room darkening drapes.
Breakfast was good.
TV not usefall no NBC,ABC,CBS channel and very few other channels to watch except old out of date programming.
Reviewed on May 11, 2026
Portland Harbor Hotel
Downtown Portland
Price was CA $3,153, price is now CA $2,476 per person
CA $2,476
per person
Jun 17 - Jun 21
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,753 reviews)
Best location in Portland. The free bikes were the highlight, We went everywhere with them. Very convenient! The staff was very nice.
Reviewed on May 10, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was CA $2,442, price is now CA $2,049 per person
CA $2,049
per person
Jun 17 - Jun 21
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (304 reviews)
This accommodation was in an excellent location for restaurants and attending events. We were able to park our car and walk without concern. We found the accommodation well furnished with a well equipped kitchen. We would have liked to stay longer and will likely return.
Reviewed on May 5, 2026
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