
Great Island Vacations from $327
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The Latest Great Island vacation packages
Price found within the past 48 hours. Click for updated prices.

Best Western Freeport Inn
Price was $412, price is now $327 per person
$327
per person
Jan 12 - Jan 17
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
7.8/10 Good! (1,013 reviews)
Room was not the cleanest. Something sticky was on the night table, a cap from a shampoo or something on the bathroom floor, curtains we were filthy and stained. The bathtub was disgusting. It’s so old and stained so it looks dirty. Cant tell if it was cleaned or not.
Did not refill my coffee pods for my last morning.
Reviewed on Nov 10, 2025

Cliff House Maine
Save 100% on your flight
Price was $1,185, price is now $730 per person
$730
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
9.4/10 Exceptional! (1,016 reviews)
Beautiful hotel. Loved the hot-tub and pool, on site restaurants were absolutely incredible and the day spa was perfect! All of the staff were lovely and helpful
Reviewed on Nov 7, 2025

84 Main
Save 100% on your flight
Price was $622, price is now $428 per person
$428
per person
Dec 20 - Dec 25
found 19 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
10/10 Exceptional! (51 reviews)
This property was absolutely beautiful and well maintained! Right in the heart of Kennebunk within walking distance to great restaurants!!
Reviewed on Oct 26, 2025

Portland Harbor Hotel
Downtown Portland
Price was $712, price is now $547 per person
$547
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.2/10 Wonderful! (1,621 reviews)
Great rooms, walk-able to everything, super clean, great staff, the restaurant is delicious and the bar has good drinks, very accommodating and lots of extras!
The 4 stars are for parking... we would like to keep our car inside the garage, to do so it must be valet, that is not an option for some people.
Otherwise, this place is perfect!
Reviewed on Nov 12, 2025

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See all available trips from Columbus to Great Island
View all tripsDiscover the most popular places to visit in Great Island
Bailey Island Bridge
4.5/5(9 reviews)
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

Portland Harbor Hotel
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $183 total per night from Nov 16 to Nov 17
$183 total
Nov 16 - Nov 17
Total with taxes and fees
9.2/10 Wonderful! (1,666 reviews)
Great rooms, walk-able to everything, super clean, great staff, the restaurant is delicious and the bar has good drinks, very accommodating and lots of extras! The 4 stars are for parking... we would like to keep our car inside the garage, to do so it must be valet, that is not an option for some ...
Reviewed on Nov 12, 2025

Clarion Hotel Portland
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $92 total per night from Nov 18 to Nov 19
$92 total
Nov 18 - Nov 19
Total with taxes and fees
7.8/10 Good! (1,222 reviews)
I've stayed here a few times and have always had a good experience. Staff is always welcoming and the rooms are
Reviewed on Nov 9, 2025

Tru by Hilton Portland Airport Area
369 Maine Mall Road, South Portland, ME
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $86 total per night from Nov 19 to Nov 20
$86 total
Nov 19 - Nov 20
Total with taxes and fees
8.8/10 Excellent! (1,609 reviews)
Absolutely
Reviewed on Nov 12, 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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- Visit Orrs Island
- Paddleworks
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- Bailey Island Bridge
- Visit Cundys Harbor
- Ash Cove Pottery
- Visit Bailey Island
- Bailey Island Vacations
- Sebasco Estates Vacations
- Visit Sebascodegan Island
- Visit Sebasco Estates
- Land's End Gift Shop
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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.



















