Search Deals onBailey Island Vacation Packages
Bailey Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Portland Harbor Hotel
Price was $1,016, price is now $773 per person
$773
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Thompson's Point are located nearby.
1/3 of the final bill was parking fees, destination amenity fees and taxes! They even taxed the amenity fees. Hidden costs for booking should be listed! Unbelievable
Reviewed on Nov 9, 2026

84 Main
Price was $1,211, price is now $872 per person
$872
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this condo in Kennebunk. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Dock Square and Kennebunk Free Library are located nearby.
The property was very spacious, well equipped, and well taken care of. There was lots of natural light and a very large outdoor deck accessible from all bedrooms and the living room.
Reviewed on Jul 17, 2026

Blind Tiger Portland - Danforth Street.
Price was $2,040, price is now $1,506 per person
$1,506
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and parking (surcharge). Popular attractions State Theatre and Cross Insurance Arena are located nearby.

Evalina Hotel
Price was $1,969, price is now $1,471 per person
$1,471
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this aparthotel in Portland. Enjoy free WiFi, parking (surcharge), and in-room washers/dryers. Popular attractions State Theatre and Thompson's Point are located nearby.

The Docent's Collection at 121 Middle Street
Price was $1,587, price is now $1,210 per person
$1,210
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions State Theatre and Thompson's Point are located nearby.
Pros: Room was nice and spacious. Kitchen had everything we needed. Location was awesome - very close to all the things we wanted to do. Excellent proximity to some of the best restaurants, including LB Kitchen, Fore Street, Central Provisions. Con’s: Couches could have benefited from some throw pillows - kinda weird without any. Bed wasn’t that comfortable - you sink in way too much. Parking was ok - just some weird communication before our arrival about where to park. Text messages from the hotel leading up to our check in said they had a lot behind the building which we parked in - only to be told during check in that the lot was only for people that booked it (fair) but their messages made it seem like that was available. Then they questioned how we even knew about the lot - which was odd considering we only knew about it because they texted us parking info.
Reviewed on Nov 8, 2026

Inn By The Sea
Price was $1,520, price is now $1,161 per person
$1,161
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.

The Docent's Collection at 178 Middle Street
Price was $1,833, price is now $1,449 per person
$1,449
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions State Theatre and Thompson's Point are located nearby.
room was very modern, however some areas did not look well cleaned (edge if the bed had some dried white liquid). the surrounding area has nice shops but is very sketchy at night. did not feel comfortable with the parking situation. also at 6am sounded like maintenance or cleaning crew was constantly in and out of the elevator making tons of noise. was good for a night but wouldnt stay again.
Reviewed on Oct 27, 2026

Portland Regency Hotel & Spa
Price was $1,028, price is now $826 per person
$826
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Thompson's Point are located nearby.
Love staying at the Portland Regency.
Great location and helpful staff.
Reviewed on Nov 9, 2026
Bailey Island Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Bailey Island Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.



Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Mon, Feb 15 - Sat, Feb 20
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$219 Roundtrip, found 1 day ago
$219
Roundtrip
found 1 day ago

Tue, Dec 8 - Mon, Dec 14
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$237 Roundtrip, found 14 hours ago
$237
Roundtrip
found 14 hours ago

Wed, Feb 24 - Sat, Feb 27
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$255 Roundtrip, found 4 hours ago
$255
Roundtrip
found 4 hours ago

Wed, Dec 2 - Sat, Dec 5
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago
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