Bailey Island Vacations from $800
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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.
Inn at Diamond Cove
Price was $1,106, price is now $800 per person
$800
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
8.8/10 Excellent! (198 reviews)
Unusual place to stay; in a renovated former army base. Huge rooms, gorgeous recent renovation/reconstruction.Expensive!
Reviewed on Jul 12, 2026
The Meadowmere Resort
Save 100% on your flight
Price was $1,440, price is now $968 per person
$968
per person
Sep 20 - Sep 26
found 1 day ago
Roundtrip flight included
Chicago (MDW) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
Excellent location and a close walk to town. Gorgeous pool and the room was very clean. I would highly recommend it.
Reviewed on Jul 12, 2026
Evalina Hotel
Downtown Portland
Save 100% on your flight
Price was $1,612, price is now $1,116 per person
$1,116
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
10/10 Exceptional! (5 reviews)
It was a spacious, clean, well thought out space with all the expected amenities. The location is ideal, and the hotel is truly a treasure.
Reviewed on Jun 28, 2026
Portland Harbor Hotel
Downtown Portland
Save 100% on your flight
Price was $1,548, price is now $1,075 per person
$1,075
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
9.4/10 Exceptional! (1,775 reviews)
Our stay was great - the location of this hotel is perfect, the staff was friendly and our room was really nice. Every morning, there was a fully stocked pantry with snacks and drinks for guests on each floor. We had a great stay and would recommend this place highly!
Reviewed on Jul 12, 2026
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Bailey Island Hotel Deals
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
$135 nightly
The price is $150 total per night from Jul 19 to Jul 20
$150 total
Jul 19 - Jul 20
Total with taxes and fees
8.2/10 Very Good! (1,551 reviews)
"Could use an update"
Reviewed on Jul 12, 2026
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
340 Park Ave Portland ME
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $198 total per night from Jul 13 to Jul 14
$198 total
Jul 13 - Jul 14
Total with taxes and fees
8.6/10 Excellent! (2,204 reviews)
"Not nice hotel and way overpriced."
Reviewed on Jul 12, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
$340 nightly
The price is $376 total per night from Jul 13 to Jul 14
$376 total
Jul 13 - Jul 14
Total with taxes and fees
9.4/10 Exceptional! (1,264 reviews)
"The room was perfect and spacious; the only downside was the view."
Reviewed on Jul 12, 2026
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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- Hunnewell Beach
- Freeport Vacations
- Wolfe's Neck Woods State Park
- Harrington House
- Two Lights State Park
- Visit Portland
- Bowdoin College
- Cundys Harbor Vacations
- Little John Island Preserve
- Popham Beach State Park
- Victoria Mansion
- Visit Freeport
- Ll Bean Flagship Store
- Casco Bay
- Wilbur's of Maine Chocolate Confections
- Downtown Portland Vacations
- Chebeague Island Vacations
- Sebasco Estates Vacations
- Bailey Island Bridge
- Casco Bay Lines Ferry Terminal
- Visit Bailey Island
- Fort Williams Park
- Visit Old Port
- Land's End Gift Shop
- Bug Light
- Bates-Morse Mountain Conservation Area
- Portland Head Light
- Bradbury Mountain State Park
- First Parish Church
- East End Beach
- Paddleworks
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
