
Great Island Vacations from $599
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The Latest Great Island vacation packages
Price found within the past 48 hours. Click for updated prices.

Dormir
Price was $665, price is now $599 per person
$599
per person
Dec 19 - Dec 22
found 1 hour ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
8.8/10 Excellent! (1,005 reviews)
Great hotel, I am glad I picked them. The room was comfortable and updated. Rooms do include a refrigerator and microwave.
Reviewed on Nov 5, 2025

Blind Tiger Portland - Danforth Street.
West End
Price was $837, price is now $682 per person
$682
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
9.6/10 Exceptional! (155 reviews)
Wish they had a liquor license and could do a cocktail hour in addition to a breakfast service. Wish they had just a tad more breakfast options. Really wish they had a key pad and front door access! LOVED the fire places in every room. Property manager was lovely and friendly. Loved the snacks available and variety.
Reviewed on Oct 27, 2025

84 Main
Price was $754, price is now $634 per person
$634
per person
Dec 19 - Dec 22
found 1 hour ago
Roundtrip non-stop flight included
Dallas (DFW) 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

Waldo Emerson Inn
Price was $913, price is now $799 per person
$799
per person
Dec 19 - Dec 22
found 1 hour ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
8.8/10 Excellent! (334 reviews)
This inn was so charming! Upon arrival, there were complimentary cookies and apple cider waiting for us. Amelia and Ron were so friendly and accommodating to ensure we had an amazing stay. Rooms were spotless and very comfortable.
Reviewed on Oct 28, 2025

Blind Tiger Portland – Carleton Street
West End
Price was $1,409, price is now $1,260 per person
$1,260
per person
Dec 26 - Dec 30
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
9.6/10 Exceptional! (117 reviews)
Great location and such an amazing day! The interiors are inspiring!
Reviewed on Nov 1, 2025
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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.
Paddleworks
Enjoy an outing to Paddleworks during your stay in Orrs Island. Wander the seaside and beaches in the area.
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.
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 30 to Dec 1
$183 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (1,685 reviews)
Great service
Reviewed on Nov 6, 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 11 to Nov 12
$92 total
Nov 11 - Nov 12
Total with taxes and fees
7.8/10 Good! (1,218 reviews)
It was clean and quiet-what I needed!
Reviewed on Nov 3, 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 13 to Nov 14
$86 total
Nov 13 - Nov 14
Total with taxes and fees
8.8/10 Excellent! (1,591 reviews)
All was as expected from Tru experiences.
Reviewed on Nov 4, 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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- Sebasco Estates Hotels
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- Cottages in Hermit Island
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- Hermit Island Hotels
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- Visit Orrs Island
- Paddleworks
- Cundys Harbor Vacations
- Visit Harpswell
- 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
- Hermit Island Vacations
- Visit Hermit Island
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- Car rentals near Harpswell
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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.


















