Great Diamond Island Pet-friendly Vacations 2026

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5* Pet-friendly vacations in Great Diamond Island

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

White Barn Inn & Spa, Auberge Collection

$1,674

per person

Nov 13 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Portland (PWM)

9.6/10 Exceptional! (124 reviews)

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3 Night Pet-friendly vacations in Great Diamond Island

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

Portland Harbor Hotel

Downtown Portland

$655

per person

Dec 18 - Dec 21

found 12 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

9.2/10 Wonderful! (1,845 reviews)

We absolutely loved this hotel. The location was perfect for our ladies trip. The staff were beyond helpful!!! And the rooms were very well maintained. thank you very much…..

Reviewed on Sep 28, 2026

Cliff House Maine

Bald Head

Save 100% on your flight

$1,171

per person

Dec 17 - Dec 20

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Portland (PWM)

9.4/10 Exceptional! (1,004 reviews)

It is a perfect place to stay I can’t think of anything I did not like can’t wait to visit again

Reviewed on Sep 27, 2026

Inn By The Sea

$919

per person

Nov 7 - Nov 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Portland (PWM)

9.6/10 Exceptional! (331 reviews)

Staff and food were both wonderful. We would definitely stay again.

Reviewed on Sep 28, 2026

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4 Night Pet-friendly vacations in Great Diamond Island

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

Blind Tiger Portland – Carleton Street

West End

$838

per person

Dec 3 - Dec 7

found 5 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Portland (PWM)

9.6/10 Exceptional! (129 reviews)

Great location and cool property. No TV though.

Reviewed on Sep 28, 2026

Evalina Hotel

Downtown Portland

$920

per person

Dec 3 - Dec 7

found 5 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Portland (PWM)

10/10 Exceptional! (11 reviews)

Better than expected. This new property was in a great location. Easy to walk to restaurants and shopping. Comfortable bed, nice bathroom and a sitting area with sofa, chair and tv. I was a little concerned because we could hear music from a nearby bar, but everything stopped by 10 o’clock. Would return.

Reviewed on Sep 25, 2026