Search Deals onBailey Island Vacation Packages
Bailey Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Harraseeket Inn & Event House
per person
Jun 28 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Portland (PWM)
Stay at this 3.5-star business-friendly hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions LL Bean Flagship Store and Freeport Historical Society are located nearby.
Portland Harbor Hotel
Save 100% on your flight
per person
Jun 28 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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
Save 100% on your flight
per person
Jun 28 - Jul 5
found 1 day 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.
The McKernan Inn
Save 100% on your flight
per person
Jun 28 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Portland (PWM)
Stay at this 3-star beach inn in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thompson's Point and Maine Mall are located nearby.
Inn at Diamond Cove
Save 100% on your flight
per person
Jun 28 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Portland (PWM)
Stay at this 3.5-star hotel in Portland. Enjoy free WiFi, 2 restaurants, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions Thompson's Point and Little Diamond Island are located nearby.
Blind Tiger Portland - Danforth Street.
Save 100% on your flight
per person
Jun 28 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Portland (PWM)
Stay at this 3.5-star B&B in Portland. Enjoy free breakfast, free WiFi, and concierge services. Popular attractions Thompson's Point and Maine Mall are located nearby.
Inn By The Sea
per person
May 22 - May 26
found 14 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) 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.
Hampton Inn Portland Downtown - Waterfront
Save 100% on your flight
per person
Jun 28 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall 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.
Sat, Apr 19 - Mon, Apr 28
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Mon, Jul 28 - Thu, Jul 31
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$117 Roundtrip, found 3 days ago
$117
Roundtrip
found 3 days ago
Tue, Apr 22 - Thu, Apr 24
LGA
LaGuardia
PWM
Portland Intl. Jetport
$167 Roundtrip, found 5 days ago
$167
Roundtrip
found 5 days ago
Thu, Apr 24 - Sun, Apr 27
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$167 Roundtrip, found 5 days ago
$167
Roundtrip
found 5 days ago
Discover Other Travel Deals
- Bailey Island Bridge Vacations
- Land's End Gift Shop Vacations
- Cobwork Bridge Vacations
- Acadia National Park Vacations
- Thompson's Point Vacations
- Maine Mall Vacations
- LL Bean Flagship Store Vacations
- Bowdoin College Vacations
- State Theatre Vacations
- Portland Head Light Vacations
- Higgins Beach Vacations
- Maine Medical Center Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
Car Rentals in Bailey Island
- Car rentals in Portland
- Car rentals in Boothbay Harbor
- Car rentals in Georgetown
- Car rentals in South Portland
- Car rentals in Freeport
- Car rentals in Scarborough
- Car rentals in Cape Elizabeth
- Car rentals in Brunswick
- Car rentals in Bath
- Car rentals in Peaks Island
- Car rentals in Falmouth
- Car rentals in Phippsburg