Great Diamond Island Pet-friendly Vacations
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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.
The Westin Portland Harborview
Downtown Portland
Price was CA $711, price is now CA $641 per person
CA $641
per person
May 1 - May 3
found 8 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Portland (PWM)
8.8/10 Excellent! (1,002 reviews)
Clean, quiet and comfortable. Exceptional team who were helpful and friendly. I actually hated to leave. Great stay!
Reviewed on Feb 28, 2026
Portland Harbor Hotel
Downtown Portland
Price was CA $1,507, price is now CA $1,272 per person
CA $1,272
per person
May 21 - May 24
found 18 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Portland (PWM)
9.2/10 Wonderful! (1,765 reviews)
Business facilities were perfect. Front desk man Roman was an all star helping us out. Whole stay was 100/100
Reviewed on Mar 4, 2026
Kennebunkport Captains Collection
Price was CA $1,071, price is now CA $942 per person
CA $942
per person
May 1 - May 3
found 8 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Portland (PWM)
9.4/10 Exceptional! (684 reviews)
Parking is great and very convenient. Staff is very friendly. Breakfast was delicious. I do think our room could use more light. Door numbers of the rooms could be bigger. The hallway is dark making it difficult to read the numbers.
Reviewed on Mar 2, 2026
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View all trips5* Pet-friendly holidays in Great Diamond Island
Price found within the past 48 hours. Click for updated prices.
White Barn Inn & Spa, Auberge Collection
Price was CA $1,596, price is now CA $1,555 per person
CA $1,555
per person
May 24 - May 26
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.4/10 Exceptional! (112 reviews)
Unbelievable! Amazing Service, and beautiful accommodations. The food was incredible as well! I’ll be back!!
Reviewed on Dec 21, 2025
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See all available trips from Columbus to Great Diamond Island
View all trips3 Night Pet-friendly holidays in Great Diamond Island
Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
Downtown Portland
Price was CA $1,507, price is now CA $1,272 per person
CA $1,272
per person
May 21 - May 24
found 18 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Portland (PWM)
9.2/10 Wonderful! (1,765 reviews)
Business facilities were perfect. Front desk man Roman was an all star helping us out. Whole stay was 100/100
Reviewed on Mar 4, 2026
Kennebunkport Captains Collection
Price was CA $1,512, price is now CA $1,343 per person
CA $1,343
per person
May 21 - May 24
found 18 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Portland (PWM)
9.4/10 Exceptional! (684 reviews)
Parking is great and very convenient. Staff is very friendly. Breakfast was delicious. I do think our room could use more light. Door numbers of the rooms could be bigger. The hallway is dark making it difficult to read the numbers.
Reviewed on Mar 2, 2026
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See all available trips from Columbus to Great Diamond Island
View all tripsPet-friendly Hotels in Great Diamond Island
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 ...
10/10 Exceptional! (18 reviews)
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.
