Great Diamond Island Vacation Packages
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4.0-star property
Portland Harbor Hotel
Downtown Portland
9.2/10 Wonderful! (1,851 reviews)
Dec 18 - Dec 21
3 night stay
Atlanta (ATL) to Portland (PWM)
Frontier Airlines • Roundtrip • Coach
Price was $565, price is now $486 per person
$486
per person
found 16 hours ago
Location A+ with easy to walk to shops and restaurants.
Bedroom was clean and had great wooden armoire, small refrigerator.
Bathroom seemed clean but lighting very low. Water pressure could be improved.
All in all a great place to stay.
Reviewed on Nov 6, 2026
3.5-star property
The Docent's Collection at 178 Middle Street
Downtown Portland
9.8/10 Exceptional! (81 reviews)
Dec 18 - Dec 21
3 night stay
Atlanta (ATL) to Portland (PWM)
Frontier Airlines • Roundtrip • Coach
Price was $787, price is now $684 per person
$684
per person
found 16 hours ago
room was very modern, however some areas did not look well cleaned (edge if the bed had some dried white liquid). the surrounding area has nice shops but is very sketchy at night. did not feel comfortable with the parking situation. also at 6am sounded like maintenance or cleaning crew was constantly in and out of the elevator making tons of noise. was good for a night but wouldnt stay again.
Reviewed on Oct 27, 2026
4.5-star property
Kennebunkport Captains Collection
9.4/10 Exceptional! (763 reviews)
Dec 18 - Dec 21
3 night stay
Atlanta (ATL) to Portland (PWM)
Frontier Airlines • Roundtrip • Coach
Price was $815, price is now $715 per person
$715
per person
found 16 hours ago
Property was absolutely amazing. We fell in love with the area and our stay at the William Jefferds House was perfect. Love the breakfast and amenities in the house. We took advantage of the free bicycle use. Definitely on our list to return.
Reviewed on Nov 5, 2026
Top rated hotels for your Great Diamond Island vacation package
The Westin Portland Harborview
157 High St Portland ME
Free Cancellation
Reserve now, pay when you stay
3.74 mi from city center
$101 nightly
The price is $112 total per night
$112 total
Dec 6 - Dec 7
Total with taxes and fees
Guests staying at The Westin Portland Harborview enjoy access to a full-service spa, a 24-hour gym, and free WiFi in public areas. Valet parking is available for USD 47 per night. Front-desk staff can answer questions 24/7, and assist with securing valuables, dry cleaning/laundry, and tours or tickets. Other amenities at this spa hotel include meeting rooms, a conference center, and a 24-hour business center.
Spa
Pet friendly
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Free Cancellation
4.9 mi from city center
$81 nightly
The price is $89 total per night
$89 total
Nov 12 - Nov 13
Total with taxes and fees
Guests staying at Clarion Hotel Portland Airport ME enjoy an indoor pool, a gym, and free WiFi in public areas. There's free parking, as well as a free airport shuttle (available on request). Multilingual staff at the 24-hour front desk can assist with luggage storage, securing valuables, and concierge services. Additional amenities include a hot tub, meeting rooms, and conference space.
Pool
Hot Tub
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Free Cancellation
Reserve now, pay when you stay
6.51 mi from city center
$88 nightly
The price is $97 total per night
$97 total
Nov 8 - Nov 9
Total with taxes and fees
At Fireside Inn & Suites Portland, guests enjoy an indoor pool, a gym, and a sauna. A stay here includes free parking. The front desk is staffed 24 hours a day to help with securing valuables and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include free WiFi in public areas, a hot tub, and conference space.
Pool
Hot Tub
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View all propertiesLowest 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.
Things to do
Portland, Maine: Hidden Histories Guided Walking Tour
$54
per adult
Portland, Maine: Hidden Histories Guided Walking Tour
$54
per adult
Portland, Maine: Black History Guided Walking Tour
$54
per adult
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