Honeymoon Vacations in Great Diamond Island 2026

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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)

Location Location. Valet parking could be more reasonable!!

Reviewed on May 24, 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

Holiday Inn Portland-By the Bay by IHG

Downtown Portland

CA $2,206

per person

Jul 25 - Jul 31

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Portland (PWM)

9/10 Wonderful! (1,553 reviews)

The room was clean, but nothing special for the price per night. I really expect a bit more for $400+/night. That said, the staff were friendly, the breakfast buffet with omelet bar was nice and good quality food (not included in price of hotel), walkable to the Old Port.

Reviewed on May 24, 2026

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3 Night Honeymoon holidays in Great Diamond Island

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

Chebeague Island Inn

CA $1,367

per person

Jul 22 - Jul 25

found 6 hours 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

The Weldon Hotel

Downtown Portland

CA $3,492

per person

Jul 22 - Jul 25

found 6 hours 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

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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 3 hours 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