Great Island Cheap Vacations
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Flight and Cheap hotel deals in Great Island
Price found within the past 48 hours. Click for updated prices.
Longfellow Hotel
Parkside
Price was CA $1,838, price is now CA $1,709 per person
CA $1,709
per person
Sep 23 - Sep 26
found 20 hours ago
Roundtrip non-stop flight included
Jackson (JAN) to Portland (PWM)
9.6/10 Exceptional! (172 reviews)
Such a cute hotel! Staff was super helpful and friendly
Reviewed on Jul 10, 2026
The Weldon Hotel
Downtown Portland
Price was CA $2,487, price is now CA $1,922 per person
CA $1,922
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Spacious with plenty of room for my family of four. Excellent kitchen, washer and dryer and stellar location close to Waterfront district.
Reviewed on Jul 5, 2026
Kennebunkport Captains Collection
Price was CA $3,009, price is now CA $2,558 per person
CA $2,558
per person
Sep 16 - Sep 20
just found
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (720 reviews)
Such a great stay over 4th of July week. The room was huge & clean, we loved using bikes on the property and the staff was so helpful.
Reviewed on Jul 8, 2026
Inn By The Sea
Price was CA $2,104, price is now CA $1,792 per person
CA $1,792
per person
Sep 23 - Sep 26
found 20 hours ago
Roundtrip non-stop flight included
Jackson (JAN) 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
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Price found within the past 48 hours. Click for updated prices.
Longfellow Hotel
Parkside
Price was CA $1,838, price is now CA $1,709 per person
CA $1,709
per person
Sep 23 - Sep 26
found 20 hours ago
Roundtrip non-stop flight included
Jackson (JAN) to Portland (PWM)
9.6/10 Exceptional! (172 reviews)
Such a cute hotel! Staff was super helpful and friendly
Reviewed on Jul 10, 2026
Inn By The Sea
Price was CA $2,104, price is now CA $1,792 per person
CA $1,792
per person
Sep 23 - Sep 26
found 20 hours ago
Roundtrip non-stop flight included
Jackson (JAN) 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
The Weldon Hotel
Downtown Portland
Price was CA $1,944, price is now CA $1,789 per person
CA $1,789
per person
Sep 23 - Sep 26
found 20 hours ago
Roundtrip non-stop flight included
Jackson (JAN) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Spacious with plenty of room for my family of four. Excellent kitchen, washer and dryer and stellar location close to Waterfront district.
Reviewed on Jul 5, 2026
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View all trips4 Night Cheap holidays in Great Island
Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites
Moody
Price was CA $1,319, price is now CA $966 per person
CA $966
per person
Aug 31 - Sep 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,008 reviews)
Great place to stay! Peaceful area with ample parking. Room was clean & spacious! Beds were comfy. Beautiful area with nice areas to sit outside. Close to many things in the area to go see & do.
Reviewed on Jul 14, 2026
Blind Tiger Portland - Danforth Street.
West End
Price was CA $4,313, price is now CA $3,221 per person
CA $3,221
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (188 reviews)
We were only there for 1 night, but the innkeeper made a great suggestion for dinner. Overall a great place and would stay again.
Reviewed on Jun 26, 2026
Evalina Hotel
Downtown Portland
Price was CA $2,806, price is now CA $2,141 per person
CA $2,141
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) 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
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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.
