Bailey Island Vacations from $393
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Your Bailey Island Vacation
With one of our vacation packages to Bailey Island, you'll have endless opportunities for relaxation and adventure. There's lots to experience, including its coastal scenery and spectacular views. If sightseeing is on the cards during your trip to Bailey Island, check out popular attractions like Bailey Island Bridge, Lands End Gift Shop and Ragged Island. A few quick clicks is all it takes to build a customized Bailey Island vacation on Expedia.
The Latest Bailey Island vacation packages
Price found within the past 48 hours. Click for updated prices.
Kennebunkport Captains Collection
Price was $508, price is now $393 per person
$393
per person
Feb 4 - Feb 7
found 5 hours ago
Roundtrip flight included
Chicago (CHI) 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
InnSeason Resorts The Falls at Ogunquit
Save 100% on your flight
Price was $703, price is now $528 per person
$528
per person
Mar 23 - Mar 30
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
9.4/10 Exceptional! (356 reviews)
Pool was fine; unfortunately sauna was not working.
Reviewed on Dec 2, 2025
Portland Regency Hotel & Spa
Downtown Portland
Price was $766, price is now $594 per person
$594
per person
Feb 13 - Feb 16
found 18 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.4/10 Exceptional! (1,512 reviews)
Very pleasant front desk personnel, spotless and comfortable room, beautiful holiday decorations.
Reviewed on Dec 28, 2025
The Docent’s Collection – Thompson Block
Downtown Portland
Price was $869, price is now $681 per person
$681
per person
Mar 19 - Mar 22
found 14 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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
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View all tripsDiscover the most popular places to visit in Bailey 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.
Cobwork Bridge
You can find out about the history of Bailey Island when you stop by Cobwork Bridge. Stroll along the seaside or seek out the hiking trails.
Bailey Island Hotel Deals
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Bailey Island ME
10/10 Exceptional! (212 reviews)
Wonderful house. Well equipped. Gorgeous view.
Reviewed on Nov 29, 2025
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, 2026
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
$89 nightly
The price is $98 total per night from Jan 25 to Jan 26
$98 total
Jan 25 - Jan 26, 2026
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
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 Bailey Island Vacation Packages
Bailey Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
Max Temp Winter | 30ºF |
Max Temp Summer | 70ºF |
Top Sights | Thomas Point Beach, Sand Beach and Wolfes Neck Woods State Park |
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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.