Great Diamond Island Pet-friendly Vacations
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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 $656, price is now $568 per person
$568
per person
Dec 24 - Dec 28
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (1,621 reviews)
Staff was sub par for a 4 star hotel. Bartender and wait staff were more concerned about discussing issues with customers than actually serving people right in front of them. Front desk staff were very curt on the phone.
Reviewed on Oct 23, 2025
Cliff House Maine
Save 100% on your flight
Price was $930, price is now $680 per person
$680
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
9.4/10 Exceptional! (1,016 reviews)
Absoltely incredible views- the cliffs were the perfect place to catch the sunrise. The restaurant was wonderful and the staff were super friendly and helpful. Extremely comfortable room and the hot tub and indoor pool were fantastic.
Reviewed on Oct 20, 2025
Kennebunkport Captains Collection
Save 100% on your flight
Price was $1,107, price is now $837 per person
$837
per person
Dec 24 - Dec 28
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (634 reviews)
Nice room and reception rooms. Comfortable bed. Vintage charm but nice modern bathroom. Lots of thoughtful touches like beach towels, umbrellas and afternoon cookies.
Reviewed on Oct 14, 2025
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View all trips5* Pet-friendly vacations in Great Diamond Island
Price found within the past 48 hours. Click for updated prices.
White Barn Inn & Spa, Auberge Collection
Price was $1,497, price is now $1,330 per person
$1,330
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Portland (PWM)
9.4/10 Exceptional! (102 reviews)
Excellent from check in to check out!
Reviewed on Oct 22, 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 $687, price is now $495 per person
$495
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Portland (PWM)
9.2/10 Wonderful! (1,621 reviews)
Staff was sub par for a 4 star hotel. Bartender and wait staff were more concerned about discussing issues with customers than actually serving people right in front of them. Front desk staff were very curt on the phone.
Reviewed on Oct 23, 2025
Cliff House Maine
Price was $1,419, price is now $1,044 per person
$1,044
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Portland (PWM)
9.4/10 Exceptional! (1,016 reviews)
Absoltely incredible views- the cliffs were the perfect place to catch the sunrise. The restaurant was wonderful and the staff were super friendly and helpful. Extremely comfortable room and the hot tub and indoor pool were fantastic.
Reviewed on Oct 20, 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.
InnSeason Resorts The Falls at Ogunquit
Price was $819, price is now $632 per person
$632
per person
Dec 24 - Dec 28
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (351 reviews)
Staff was great and room was exactly what we needed with lots of space!
Reviewed on Oct 19, 2025
Kennebunkport Captains Collection
Save 100% on your flight
Price was $1,107, price is now $837 per person
$837
per person
Dec 24 - Dec 28
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (634 reviews)
Nice room and reception rooms. Comfortable bed. Vintage charm but nice modern bathroom. Lots of thoughtful touches like beach towels, umbrellas and afternoon cookies.
Reviewed on Oct 14, 2025
Don't see what you're looking for?
See all available trips from Columbus to Great Diamond Island
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 Thompson's Point and Little Diamond Island are located ...
Amazing Ocean View Summer Cottage Rental w/ Boat Mooring on Great Diamond Island
Great Diamond Island
Book a stay at this family-friendly vacation home in Portland. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Thompson's Point and Little ...
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.