Search Deals onBailey Island Vacation Packages
Bailey Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Old Orchard Beach Inn
Price was $558, price is now $465 per person
$465
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Old Orchard Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Palace Playland and Old Orchard Beach are located nearby.
Tout était bien à l'exception de la grandeur de la grandeur de la salle de bain et la très pauvre performance du WiFi
Reviewed on Jul 17, 2026
Inn at Diamond Cove
Save 100% on your flight
Price was $1,463, price is now $974 per person
$974
per person
Sep 12 - Sep 17
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, 2 restaurants, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions Casco Bay Lines Ferry Terminal and Cross Insurance Arena are located nearby.
Unusual place to stay; in a renovated former army base. Huge rooms, gorgeous recent renovation/reconstruction.Expensive!
Reviewed on Jul 12, 2026
Blind Tiger Portland - Danforth Street.
Save 100% on your flight
Price was $1,295, price is now $877 per person
$877
per person
Sep 21 - Sep 23
found 3 hours ago
Roundtrip non-stop 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.
We were only there for 1 night, but the innkeeper made a great suggestion for dinner. Overall a great place and would stay again.
Reviewed on Jun 26, 2026
Evalina Hotel
Save 100% on your flight
Price was $1,630, price is now $1,123 per person
$1,123
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop 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 Cross Insurance Arena and Casco Bay Lines Ferry Terminal are located nearby.
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
Blind Tiger Portland – Carleton Street
Price was $1,031, price is now $778 per person
$778
per person
Sep 21 - Sep 23
found 3 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions State Theatre and Thompson's Point are located nearby.
Excellent private boutique home, converted to hotel. No person greets you and there is no welcome desk. You put in a code on the door to enter and instructions are given via text. No elevator and 3 stories, so keep that in mind. Would HIGHLY recommend.
Reviewed on Jul 16, 2026
The Docent's Collection at 121 Middle Street
Price was $1,234, price is now $990 per person
$990
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions Cross Insurance Arena and State Theatre are located nearby.
Beautiful place to stay
Reviewed on Jul 15, 2026
The Weldon Hotel
Price was $1,427, price is now $1,158 per person
$1,158
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions State Theatre and Casco Bay Lines Ferry Terminal are located nearby.
Spacious with plenty of room for my family of four. Excellent kitchen, washer and dryer and stellar location close to Waterfront district.
Reviewed on Jul 5, 2026
Kennebunkport Captains Collection
Price was $1,744, price is now $1,454 per person
$1,454
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this luxury hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dock Square and Wells Beach are located nearby.
Everything about this property was perfect
Reviewed on Jul 17, 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.
Wed, Sep 16 - Wed, Sep 23
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$152 Roundtrip, found 4 days ago
$152
Roundtrip
found 4 days ago
Mon, Aug 17 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$192 Roundtrip, just found
$192
Roundtrip
just found
Tue, Sep 8 - Sat, Sep 12
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$196 Roundtrip, found 1 day ago
$196
Roundtrip
found 1 day ago
Wed, Aug 5 - Sat, Aug 22
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$208 Roundtrip, found 2 days ago
$208
Roundtrip
found 2 days ago
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