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.
Inn By The Sea
Save 100% on your flight
Price was $2,082, price is now $1,514 per person
$1,514
per person
Jul 5 - Jul 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (312 reviews)
Couldn't recommend this hotel enough - it was the perfect stay! Staff are incredibly helpful, the rooms are amazing, and the spa was awesome! 15 minutes from Portland and right on the beach, it couldn't get better!
Reviewed on Apr 22, 2026
Grasshopper Inn
Save 100% on your flight
Price was $1,942, price is now $1,426 per person
$1,426
per person
Jun 7 - Jun 12
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.8/10 Exceptional! (71 reviews)
We had a fantastic stay at Grasshopper Inn and will definitely return when back in the area. Clean, friendly staff and brilliant location.
Reviewed on Oct 22, 2025
Portland Harbor Hotel
Downtown Portland
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Price was $1,616, price is now $1,200 per person
$1,200
per person
Jun 18 - Jun 21
found 23 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
9.2/10 Wonderful! (1,751 reviews)
We (and our kids!) loved the “pantry” on each floor — fruit, snacks, cookies, tea, coffee. It was a much-appreciated surprise. Room was clean and quiet, and all staff were friendly and helpful.
Reviewed on Apr 29, 2026
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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
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Price was $5,419, price is now $4,319 per person
$4,319
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (114 reviews)
Custer service was excellent
Reviewed on Apr 11, 2026
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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.
The Weldon Hotel
Downtown Portland
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Price was $1,156, price is now $826 per person
$826
per person
Jul 5 - Jul 8
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Lovely suite! Comfy king bed, everything spotless,
Great location. Would stay here again
Reviewed on Apr 23, 2026
Cliff House Maine
Bald Head
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Price was $1,823, price is now $1,269 per person
$1,269
per person
Jun 11 - Jun 14
found 5 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
all was great. my favorite place!
Reviewed on Apr 29, 2026
Inn By The Sea
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Price was $1,548, price is now $1,140 per person
$1,140
per person
Jul 5 - Jul 8
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (312 reviews)
Couldn't recommend this hotel enough - it was the perfect stay! Staff are incredibly helpful, the rooms are amazing, and the spa was awesome! 15 minutes from Portland and right on the beach, it couldn't get better!
Reviewed on Apr 22, 2026
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View all trips4 Night Pet-friendly vacations in Great Diamond Island
Price found within the past 48 hours. Click for updated prices.
Cambria Hotel Portland Downtown-Old Port
Downtown Portland
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Price was $1,496, price is now $1,011 per person
$1,011
per person
Jul 18 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.4/10 Exceptional! (1,197 reviews)
Always a beautiful stay here, great location, friendly staff and great bartender!
I especially love the bathroom set up, great space, lighting and shower!
Reviewed on May 3, 2026
Meadowmere Resort
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Price was $1,691, price is now $1,070 per person
$1,070
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
Very well kept… great staff we had a great time
Reviewed on Apr 14, 2026
Portland Harbor Hotel
Downtown Portland
Save 100% on your flight
Price was $2,016, price is now $1,432 per person
$1,432
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
9.2/10 Wonderful! (1,751 reviews)
We (and our kids!) loved the “pantry” on each floor — fruit, snacks, cookies, tea, coffee. It was a much-appreciated surprise. Room was clean and quiet, and all staff were friendly and helpful.
Reviewed on Apr 29, 2026
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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 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 ME
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 ...
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.
