
Great Island Vacations from $511
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The Latest Great Island vacation packages
Price found within the past 48 hours. Click for updated prices.

InnSeason Resorts The Falls at Ogunquit
Price was $656, price is now $511 per person
$511
per person
Feb 1 - Feb 7
found 15 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Portland (PWM)
9.4/10 Exceptional! (356 reviews)
Pool was fine; unfortunately sauna was not working.
Reviewed on Dec 2, 2025

The Docent’s Collection – Thompson Block
Downtown Portland
Price was $873, price is now $685 per person
$685
per person
Mar 19 - Mar 22
found 9 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
This was a great stay! Had everything we wanted. Location was excellent.
Reviewed on Dec 24, 2025


Blind Tiger Portland - Danforth Street.
West End
Price was $1,061, price is now $840 per person
$840
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Portland (PWM)
9.6/10 Exceptional! (161 reviews)
The property is beautiful, the staff is kind, and the rooms are spacious and clean. It was great to have a safe place to park the car while having so many things to do within walking distance. Being able to grab a quick breakfast before heading out was great too! We loved our stay here!
Reviewed on Nov 23, 2025

Kennebunkport Captains Collection
Price was $1,045, price is now $830 per person
$830
per person
Feb 1 - Feb 7
found 15 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Portland (PWM)
9.4/10 Exceptional! (649 reviews)
Beautiful property in a great location—an easy walk to town. It felt warm and cozy for the holidays, with lovely winter touches throughout. Breakfast was nice, with a different featured item each day. We especially enjoyed the gas fireplace and hot cocoa bar.
On the downside, there is now a new “resort” fee. They attempted to charge an extra $27 per night even though my stay was paid in full months earlier. Because my reservation was made before the fee was introduced, it didn’t apply—but it’s still unclear what winter amenities would justify this charge.
Reviewed on Dec 28, 2025
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Bailey Island Bridge
Find out about the history of Bailey Island when you spend time at Bailey Island Bridge. Stroll along the seaside or seek out the hiking trails.
Land's End Gift Shop
Enjoy an outing to Land's End Gift Shop during your stay in Bailey Island. While you're in the area, find time to visit its shops.
Paddleworks
Enjoy an outing to Paddleworks during your stay in Orrs Island. Wander the seaside and beaches in the area.
Great Island Hotel Deals

Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $88 total per night from Jan 11 to Jan 12
$88 total
Jan 11 - Jan 12
Total with taxes and fees
7.8/10 Good! (1,307 reviews)
The airport shuttle was very convenient and appreciated on an early and snowy Christmas Eve morning. Night and morning desk staff were very helpful and friendly.
Reviewed on Dec 26, 2025

The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $108 total per night from Jan 25 to Jan 26
$108 total
Jan 25 - Jan 26
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
Staff was so friendly and had great dining recommendations. Room was super clean. Hotel was quiet and located in a perfect spot around the corner from the comedy show we went to see. Everything was so nice and good luck to the ginger bread house decoration competitors! We hope our choice wins!
Reviewed on Dec 22, 2025

Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $152 total per night from Jan 5 to Jan 6
$152 total
Jan 5 - Jan 6
Total with taxes and fees
9.4/10 Exceptional! (1,558 reviews)
Perfect location- lovely little hotel bar, nice room - friendly staff
Reviewed on Dec 29, 2025
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.
Find the Best Great Island Vacation Packages
Great Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
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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.


















