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 $1,252, price is now $1,042 per person
$1,042
per person
Dec 26 - Jan 1
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Old hotel recently updated. Great location in Old Port in walking distance of restaurants and shop. Very helpful staff. Easy valet parking. They charge a resort fee but you get it back as credit to use for breakfast or at the bar. Great outdoor patio area with gas fire pit. Great vibe for adult travelers.
Reviewed on Nov 14, 2026
Mayville Union House
Save 100% on your flight
Price was $2,454, price is now $1,894 per person
$1,894
per person
Dec 23 - Dec 30
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this B&B in Bethel. Enjoy free WiFi, free parking, and housekeeping. Popular attractions Sunday River and Bethel Pathway are located nearby.
Blind Tiger Portland - Danforth Street.
Price was $2,849, price is now $2,217 per person
$2,217
per person
Dec 26 - Jan 1
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
The Docent's Collection at 121 Middle Street
Price was $1,897, price is now $1,544 per person
$1,544
per person
Dec 26 - Jan 1
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Our only place to stay in Portland!
Reviewed on Nov 14, 2026
Blind Tiger Portland – Carleton Street
Price was $1,568, price is now $1,288 per person
$1,288
per person
Dec 26 - Jan 1
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions State Theatre and Cross Insurance Arena are located nearby.
Inn By The Sea
Price was $1,964, price is now $1,613 per person
$1,613
per person
Dec 26 - Jan 1
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Evalina Hotel
Price was $2,116, price is now $1,842 per person
$1,842
per person
Dec 26 - Jan 1
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Portland Regency Hotel & Spa
Price was $1,260, price is now $1,115 per person
$1,115
per person
Dec 26 - Jan 1
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
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
$224 Roundtrip, found 15 hours ago
$224
Roundtrip
found 15 hours ago
Sun, Feb 28 - Wed, Mar 10
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$247 Roundtrip, just found
$247
Roundtrip
just found
Wed, Feb 24 - Sat, Feb 27
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$275 Roundtrip, found 8 hours ago
$275
Roundtrip
found 8 hours ago
Wed, Dec 2 - Sat, Dec 5
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$363 Roundtrip, found 4 days ago
$363
Roundtrip
found 4 days ago
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