Honeymoon Vacations in Great Diamond Island 2026

Plan, book, travel with confidence
Better together
Save up to CA $4,200 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Flight and Honeymoon hotel deals in Great Diamond Island

Price found within the past 48 hours. Click for updated prices.

Chebeague Island Inn

CA $1,975

per person

Jun 27 - Jul 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

8.8/10 Excellent! (77 reviews)

Charming and easy access to the Golf Course

Reviewed on Sep 21, 2025

Portland Harbor Hotel

Downtown Portland

CA $2,299

per person

Jun 27 - Jul 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

9.4/10 Exceptional! (1,762 reviews)

The New England decor was pleasant. The free snack station on each floor was great (fruit, yogurt, granola, pastries, trail mix bars, coffee, multiple tea flavors, cookies) are a nice edition. We avoided the destination/resort fee be having breakfast or cocktails each day. The outdoor fire pits were enjoyable

Reviewed on May 23, 2026

The Weldon Hotel

Downtown Portland

CA $3,204

per person

Jun 27 - Jul 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) 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

Longfellow Hotel

Parkside

CA $2,993

per person

Jun 27 - Jul 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

9.6/10 Exceptional! (161 reviews)

Clean, comfortable rooms. Hotel does have a few food options near by but car service was wonderful as it’s not near most of the restaurants & shops. Overall great hotel!

Reviewed on May 17, 2026

The Westin Portland Harborview

Downtown Portland

CA $2,083

per person

Jun 27 - Jul 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

8.8/10 Excellent! (1,005 reviews)

Great staff that is very helpful. Lots of homeless surrounding the entire area.

Reviewed on May 23, 2026

Don't see what you're looking for?

See all available trips from Columbus to Great Diamond Island

View all trips

4 Night Honeymoon holidays in Great Diamond Island

Price found within the past 48 hours. Click for updated prices.

USA Inn

CA $1,131

per person

Jul 13 - Jul 17

found 1 hour ago

Roundtrip non-stop flight included

Toronto (YYZ) to Portland (PWM)

8/10 Very Good! (777 reviews)

The girl that works at the check in desk allowed us to check in early which helped us get some sleep after an early flight. Walls are thick. Very quiet. The beach is right down the road and if you have pets, Drake’s Island is one of my favorites. There are lots of really good restaurants nearby. Beachfire has really good food. Horizons Family Restaurant is literally in walking distance from the Inn which serves breakfast. Mike’s All Day Breakfast in Kennebunk was really good. If you like Mexican you should check out Barrio in Portsmouth, NH.

Reviewed on May 17, 2026