Great Diamond Island Scuba Diving Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Flight and Scuba Diving hotel deals in Great Diamond Island
Price found within the past 48 hours. Click for updated prices.
Chebeague Island Inn
Price was CA $1,519, price is now CA $1,428 per person
CA $1,428
per person
Aug 18 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
8.8/10 Excellent! (78 reviews)
An absolutely beautiful property and staff were incredibly kind and helpful!
We had a late arrival and the two young gentlemen were waiting at the dock and they helped my sister and I with all our bags.
The entire property was very clean and there were incredible views of the water and golf course.
Looking forward to returning!
Reviewed on Jun 27, 2026
The Weldon Hotel
Downtown Portland
Price was CA $3,078, price is now CA $2,529 per person
CA $2,529
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Lovely suite! Comfy king bed, everything spotless,
Great location. Would stay here again
Reviewed on Apr 23, 2026
Portland Harbor Hotel
Downtown Portland
Price was CA $2,256, price is now CA $1,874 per person
CA $1,874
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.4/10 Exceptional! (1,771 reviews)
Great room. Excellent location nice courtyard for food and drinks with firepit
Reviewed on Jul 1, 2026
Longfellow Hotel
Parkside
Price was CA $2,209, price is now CA $2,120 per person
CA $2,120
per person
Sep 24 - Sep 27
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (172 reviews)
The staff was excellent. The rooms were a little tight. The area around the hotel seemed a little sketchy but it was safe.
Reviewed on Jun 22, 2026
Don't see what you're looking for?
See all available trips from Columbus to Great Diamond Island
View all trips3 Night Scuba Diving holidays in Great Diamond Island
Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
Downtown Portland
Price was CA $2,090, price is now CA $1,819 per person
CA $1,819
per person
Sep 24 - Sep 27
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,771 reviews)
Great room. Excellent location nice courtyard for food and drinks with firepit
Reviewed on Jul 1, 2026
Longfellow Hotel
Parkside
Price was CA $2,209, price is now CA $2,120 per person
CA $2,120
per person
Sep 24 - Sep 27
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (172 reviews)
The staff was excellent. The rooms were a little tight. The area around the hotel seemed a little sketchy but it was safe.
Reviewed on Jun 22, 2026
The Weldon Hotel
Downtown Portland
Price was CA $2,265, price is now CA $2,182 per person
CA $2,182
per person
Sep 24 - Sep 27
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Lovely suite! Comfy king bed, everything spotless,
Great location. Would stay here again
Reviewed on Apr 23, 2026
Don't see what you're looking for?
See all available trips from Columbus to Great Diamond Island
View all trips4 Night Scuba Diving holidays in Great Diamond Island
Price found within the past 48 hours. Click for updated prices.
The Weldon Hotel
Downtown Portland
Price was CA $3,078, price is now CA $2,529 per person
CA $2,529
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Lovely suite! Comfy king bed, everything spotless,
Great location. Would stay here again
Reviewed on Apr 23, 2026
Portland Harbor Hotel
Downtown Portland
Price was CA $2,256, price is now CA $1,874 per person
CA $1,874
per person
Aug 17 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.4/10 Exceptional! (1,771 reviews)
Great room. Excellent location nice courtyard for food and drinks with firepit
Reviewed on Jul 1, 2026
Don't see what you're looking for?
See all available trips from Columbus to Great Diamond Island
View all tripsThings to do
Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour
CA $126
per adult
100% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
CA $24
per traveller
100% of travellers recommend
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
