Deals on vacations and trips to Bailey Island
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Bailey Island flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Hampton Inn Freeport/Brunswick
Price was $659, price is now $591 per person
$591
per person
Dec 26 - Dec 30
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Kennebunkport Captains Collection
Price was $1,476, price is now $1,234 per person
$1,234
per person
Dec 26 - Dec 30
found 23 hours ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. A garden, luggage storage, and concierge services are also on offer.
Blind Tiger Portland - Danforth Street.
West End
Price was $1,338, price is now $1,176 per person
$1,176
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
This bed & breakfast doesn't skimp on freebies - guests receive free breakfast and free WiFi. Luggage storage and concierge services are also provided.
The Kennebunk Inn
Price was $716, price is now $641 per person
$641
per person
Dec 26 - Dec 30
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a grocery/convenience store, and a library are also on offer.
White Barn Inn & Spa, Auberge Collection
Price was $1,810, price is now $1,631 per person
$1,631
per person
Dec 26 - Dec 30
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and airport shuttle. Enjoy the seasonal outdoor pool and perks like free valet parking.
Top Bailey Island hotels deals
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Free Cancellation
Reserve now, pay when you stay
$83 nightly
The price is $92 total per night
$92 total
Nov 20 - Nov 21
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the hot tub and perks like free self parking and a free cruise terminal shuttle.
Pool
Hot Tub
The Westin Portland Harborview
157 High St Portland ME
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $98 total per night
$98 total
Dec 3 - Dec 4
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.
Spa
Pet friendly
Portland Harbor Hotel
468 Fore Street Portland ME
Free Cancellation
Reserve now, pay when you stay
$142 nightly
The price is $157 total per night
$157 total
Nov 23 - Nov 24
Total with taxes and fees
This hotel features 3 coffee shops/cafes and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a 24-hour front desk.
Pet friendly
Free WiFi
DoubleTree by Hilton Hotel Portland
363 Maine Mall Rd South Portland ME
Free Cancellation
Reserve now, pay when you stay
$74 nightly
The price is $81 total per night
$81 total
Nov 26 - Nov 27
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free self parking and a free airport shuttle. A business center, a coffee shop, and free WiFi in public areas are also on offer.
Pool
Free airport shuttle
Holiday Inn Portland-By the Bay by IHG
88 Spring St Portland ME
Free Cancellation
$78 nightly
The price is $86 total per night
$86 total
Nov 30 - Dec 1
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like a free area shuttle.
Pool
Free airport shuttle
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.
Popular places to visit
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.
Frequently asked questions
Photos of local treasures
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