Great Diamond Island Mountain Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 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 Mountain hotel deals in Great Diamond Island
Price found within the past 48 hours. Click for updated prices.
84 Main
Price was CA $1,318, price is now CA $1,144 per person
CA $1,144
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Portland (PWM)
10/10 Exceptional! (52 reviews)
Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities.
Reviewed on Dec 29, 2025
Portland Harbor Hotel
Downtown Portland
Price was CA $1,319, price is now CA $1,168 per person
CA $1,168
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Really nice room. Tub, separate shower, nice linens.
Reviewed on Feb 7, 2026
Inn By The Sea
Price was CA $1,714, price is now CA $1,558 per person
CA $1,558
per person
Apr 24 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (288 reviews)
Room was ready early friendly staff and room is better than expected
Reviewed on Nov 16, 2025
Kennebunkport Captains Collection
Price was CA $1,547, price is now CA $1,437 per person
CA $1,437
per person
Apr 24 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (649 reviews)
The breakfast menu was fresh. The staff is friendly, helpful, and fantastic. Walkable to many things downtown for food but do note that many restaurants close during winter (off-season). Loved it! Would stay again.
Reviewed on Jan 3, 2026
The Westin Portland Harborview
Downtown Portland
Price was CA $1,263, price is now CA $1,177 per person
CA $1,177
per person
Apr 24 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (1,001 reviews)
Room and room service was great. Awesome location as well.
Reviewed on Feb 8, 2026
Don't see what you're looking for?
See all available trips from Columbus to Great Diamond Island
View all trips3 Night Mountain holidays in Great Diamond Island
Price found within the past 48 hours. Click for updated prices.
84 Main
Price was CA $1,318, price is now CA $1,144 per person
CA $1,144
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Portland (PWM)
10/10 Exceptional! (52 reviews)
Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities.
Reviewed on Dec 29, 2025
Portland Harbor Hotel
Downtown Portland
Price was CA $1,319, price is now CA $1,168 per person
CA $1,168
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Really nice room. Tub, separate shower, nice linens.
Reviewed on Feb 7, 2026
Inn By The Sea
Price was CA $1,714, price is now CA $1,558 per person
CA $1,558
per person
Apr 24 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (288 reviews)
Room was ready early friendly staff and room is better than expected
Reviewed on Nov 16, 2025
Don't see what you're looking for?
See all available trips from Columbus to Great Diamond Island
View all tripsMore 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.
