Pet-friendly Vacations in Great Diamond Island 2026

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Flight and Pet-friendly hotel deals in Great Diamond Island

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

Holiday Inn Portland-By the Bay by IHG

Downtown Portland

CA $1,140

per person

Nov 26 - Nov 29

found 23 hours ago

Roundtrip flight included

Halifax (YHZ) to Portland (PWM)

9/10 Wonderful! (1,644 reviews)

Portland Harbor Hotel

Downtown Portland

CA $1,300

per person

Nov 26 - Nov 29

found 23 hours ago

Roundtrip flight included

Halifax (YHZ) 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

The Weldon Hotel

Downtown Portland

CA $1,736

per person

Nov 26 - Nov 29

found 23 hours ago

Roundtrip flight included

Halifax (YHZ) to Portland (PWM)

9.8/10 Exceptional! (115 reviews)

Longfellow Hotel

Parkside

CA $1,486

per person

Nov 26 - Nov 29

found 23 hours ago

Roundtrip flight included

Halifax (YHZ) to Portland (PWM)

9.6/10 Exceptional! (192 reviews)

This hotel is amazing. Friendly staff- really good food and the spa was great.

Reviewed on Sep 21, 2026

The Westin Portland Harborview

Downtown Portland

CA $1,178

per person

Nov 26 - Nov 29

found 23 hours ago

Roundtrip flight included

Halifax (YHZ) to Portland (PWM)

9/10 Wonderful! (1,007 reviews)

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3 Night Pet-friendly holidays in Great Diamond Island

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

Portland Harbor Hotel

Downtown Portland

CA $1,300

per person

Nov 26 - Nov 29

found 23 hours ago

Roundtrip flight included

Halifax (YHZ) 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

The Weldon Hotel

Downtown Portland

CA $1,736

per person

Nov 26 - Nov 29

found 23 hours ago

Roundtrip flight included

Halifax (YHZ) to Portland (PWM)

9.8/10 Exceptional! (115 reviews)

Longfellow Hotel

Parkside

CA $1,486

per person

Nov 26 - Nov 29

found 23 hours ago

Roundtrip flight included

Halifax (YHZ) to Portland (PWM)

9.6/10 Exceptional! (192 reviews)

This hotel is amazing. Friendly staff- really good food and the spa was great.

Reviewed on Sep 21, 2026

Don't see what you're looking for?

See all available trips from Columbus to Great Diamond Island

View all trips

Pet-friendly Hotels in Great Diamond Island

Amazing Ocean View Summer Cottage Rental w/ Boat Mooring on Great Diamond Island

Great Diamond Island ME

22 min drive from Maine Mall

Book a stay at this family-friendly vacation home in Portland. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Cross Insurance Arena and ...

10/10 Exceptional! (20 reviews)

"This charming Maine cottage is located at the end of a quiet dirt lane in a serene setting with beautiful ocean views, rocky beach access, gorgeous sunsets, comfortable accommodations within easy access to the ferry. I live in Maine and it surpassed even my expectations. If you are looking for relaxation, ..."

Reviewed on Jul 13, 2026

See all 2,429 properties in Great Diamond Island

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.