Adults Only Vacations in Great Diamond Island 2026

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Flight and Adults Only hotel deals in Great Diamond Island

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

Chebeague Island Inn

CA $1,325

per person

Sep 4 - Sep 8

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Portland (PWM)

8.8/10 Excellent! (82 reviews)

Kennebunkport Captains Collection

CA $1,596

per person

Sep 13 - Sep 16

found 23 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

9.4/10 Exceptional! (727 reviews)

Great location! Easy walk to shops and short bike to Walkers Point. Staff super helpful!

Reviewed on Jul 31, 2026

The Weldon Hotel

Downtown Portland

CA $2,056

per person

Sep 13 - Sep 16

found 23 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

9.8/10 Exceptional! (102 reviews)

Great location. Friendly staff.

Reviewed on Jul 31, 2026

Longfellow Hotel

Parkside

CA $1,749

per person

Sep 13 - Sep 16

found 23 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

9.6/10 Exceptional! (178 reviews)

It’s great!

Reviewed on Jul 31, 2026

Portland Harbor Hotel

Downtown Portland

CA $1,658

per person

Sep 13 - Sep 16

found 23 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

9.4/10 Exceptional! (1,781 reviews)

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3 Night Adults Only holidays in Great Diamond Island

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

Kennebunkport Captains Collection

CA $1,596

per person

Sep 13 - Sep 16

found 23 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

9.4/10 Exceptional! (727 reviews)

Great location! Easy walk to shops and short bike to Walkers Point. Staff super helpful!

Reviewed on Jul 31, 2026

The Weldon Hotel

Downtown Portland

CA $2,056

per person

Sep 13 - Sep 16

found 23 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

9.8/10 Exceptional! (102 reviews)

Great location. Friendly staff.

Reviewed on Jul 31, 2026

Longfellow Hotel

Parkside

CA $1,749

per person

Sep 13 - Sep 16

found 23 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

9.6/10 Exceptional! (178 reviews)

It’s great!

Reviewed on Jul 31, 2026

Don't see what you're looking for?

See all available trips from Columbus to Great Diamond Island

View all trips

4 Night Adults Only holidays in Great Diamond Island

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

Ramada Plaza by Wyndham Portland

Nasons Corner

CA $800

per person

Oct 14 - Oct 18

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Portland (PWM)

7.8/10 Good! (1,009 reviews)

There is a serious moisture problem; the carpet felt wet the entire time. We were in a non-smoking room but people in neighboring rooms would smoke out on the patio and that would waft into our room even with the patio door closed.

Reviewed on Aug 3, 2026