Search Deals onBailey Island Vacation Packages
Bailey Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Dormir
per person
Oct 23 - Oct 26
found 4 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this 3-star business-friendly hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Sebago Lake and Seacoast Adventure are located nearby.
Inn By The Sea
Save 100% on your flight
per person
Oct 23 - Oct 26
found 4 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this 4-star luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.
Cliff House Maine
Save 100% on your flight
per person
Oct 17 - Oct 19
found 9 hours ago
Roundtrip flight included
Washington (DCA) to Portland (PWM)
Stay at this 4.5-star luxury resort in Cape Neddick. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Ogunquit Beach and Perkins Cove are located nearby.
Blind Tiger Portland – Carleton Street
Save 100% on your flight
per person
Oct 23 - Oct 26
found 4 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this 3.5-star B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thompson's Point and Maine Mall are located nearby.
Portland Harbor Hotel
Save 100% on your flight
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Washington (DCA) to Portland (PWM)
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
Chebeague Island Inn
per person
Sep 25 - Sep 28
found 20 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Portland (PWM)
Stay at this 4-star beach hotel in Chebeague Island. Enjoy free WiFi, breakfast (surcharge), and a free ferry terminal shuttle. Popular attractions Little John Island Preserve and Winslow Memorial Park are located nearby.
InnSeason Resorts The Falls at Ogunquit
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Portland (PWM)
Stay at this motel in Ogunquit. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Ogunquit Beach and Moody Beach are located nearby.
Ogunquit River Inn & Suites
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Portland (PWM)
Stay at this 3-star business-friendly hotel in Ogunquit. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ogunquit Beach and Moody Beach 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.
Tue, Oct 14 - Tue, Oct 21
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$99 Roundtrip, found 22 hours ago
$99
Roundtrip
found 22 hours ago
Tue, Sep 16 - Tue, Sep 30
LGA
LaGuardia
PWM
Portland Intl. Jetport
$120 Roundtrip, found 2 days ago
$120
Roundtrip
found 2 days ago
Sat, Sep 6 - Fri, Sep 12
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$149 Roundtrip, found 8 hours ago
$149
Roundtrip
found 8 hours ago
Mon, Aug 25 - Thu, Aug 28
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$160 Roundtrip, found 3 days ago
$160
Roundtrip
found 3 days ago
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