Great Diamond Island Pet-friendly Vacations
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Photo by Robbie Martin
Top Pet-friendly vacation packages in Great Diamond Island
Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
Downtown Portland
Price was $826, price is now $649 per person
$649
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Very clean, perfect location, staff was very friendly and helpful!
Reviewed on Dec 9, 2025
Cliff House Maine
Price was $1,182, price is now $902 per person
$902
per person
Jan 16 - Jan 19
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
My husband and I had a wonderful time. Breakfast, lunch, and dinner was delicious, drinks were crafted just right. We absolutely loved the outdoor hot tub. Our stay was everything we expected. Thank you.
Reviewed on Dec 8, 2025
Kennebunkport Captains Collection
Price was $806, price is now $724 per person
$724
per person
Jan 16 - Jan 19
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (649 reviews)
We loved the town, this B&B, and our time in Kennebunkport. The room was cozy and perfect; the staff was very helpful and kind; and the meals were great! Thank you!
Reviewed on Dec 10, 2025
The Weldon Hotel
Downtown Portland
Price was $917, price is now $838 per person
$838
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.8/10 Exceptional! (86 reviews)
Clean space, all the amenities needed for travel and an enjoyable stay. Location was perfect for walking to do many great local shops and restaurants.
Staff was easy to contact and quick to respond
Reviewed on Nov 28, 2025
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View all trips3 Night Pet-friendly vacations in Great Diamond Island
Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
Downtown Portland
Price was $826, price is now $649 per person
$649
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Very clean, perfect location, staff was very friendly and helpful!
Reviewed on Dec 9, 2025
Cliff House Maine
Price was $1,182, price is now $902 per person
$902
per person
Jan 16 - Jan 19
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
My husband and I had a wonderful time. Breakfast, lunch, and dinner was delicious, drinks were crafted just right. We absolutely loved the outdoor hot tub. Our stay was everything we expected. Thank you.
Reviewed on Dec 8, 2025
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See all available trips from Columbus to Great Diamond Island
View all trips4 Night Pet-friendly vacations in Great Diamond Island
Price found within the past 48 hours. Click for updated prices.
Old Orchard Beach Inn
Price was $645, price is now $591 per person
$591
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Portland (PDX) to Portland (PWM)
8.2/10 Very Good! (1,000 reviews)
We had a turret room with large windows affording a nice view of the ocean at sunrise (the leaves were off the trees over offseason holiday weekend). Very clean, attractive buildings. We were initially confused about the office location but staff were easy to contact, super responsive and accommodating.
Reviewed on Nov 29, 2025
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View all tripsTop Pet-friendly Great Diamond Island Hotels
Cozy Coveside Island Retreat
Portland ME
Stay at this vacation home in Portland. Enjoy a fitness center and laundry facilities. Popular attractions Little Diamond Island and Fort Gorges are located ...
Amazing Ocean View Summer Cottage Rental w/ Boat Mooring on Great Diamond Island
Great Diamond Island ME
Book a stay at this family-friendly vacation home in Portland. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Little Diamond Island and ...
Amazing Vacation
This house is a classic Maine island camp. We loved every bit of our stay here. We will be back!!
Reviewed on Aug 31, 2024
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.