Bailey Island Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$2,500 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Bailey Island Holiday
With one of our holiday packages to Bailey Island, you'll have limitless opportunities for adventure and relaxation. There's a lot to look forward to, including its coastal scenery and spectacular views. If your trip to Bailey Island includes a little sightseeing, drop by well-known attractions like Bailey Island Bridge, Lands End Gift Shop and Eagle Island. Your Bailey Island holiday is clicks away. Explore hotels, airfares and more on Expedia for an adventure that's tailored just for you.
Bailey Island Holiday
Bailey Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 21ºC |
Top Sights | Sand Beach, Thomas Point Beach and Wolfes Neck Woods State Park |
Our pick of the best Bailey Island Hotel Deals
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Fully refundable
AU$118
1 Sept - 2 Sept
includes taxes & fees
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
AU$204
1 Sept - 2 Sept
includes taxes & fees
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
AU$144
8 Sept - 9 Sept
includes taxes & fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Bailey Island attractions
Bailey Island Bridge
9.2/10 (10 reviews)
The world's only cribstone bridge connects Bailey Island with unique granite slabs that allow tides to flow freely. Drive or walk across this 1926 engineering marvel for spectacular coastal views.
Land's End Gift Shop
10.0/10 (1 review)
Perched at Bailey Island's southern tip, this charming shop offers an array of Maine-made treasures. Browse two levels of local crafts and speciality foods while enjoying Casco Bay views from the rocky coastline.
Cobwork Bridge
10.0/10 (1 review)
The Bailey Island Bridge's unique granite cribstone design allows tides to flow freely through its structure. Drive across this engineering marvel for stunning Casco Bay views—America's only bridge of its kind.
Frequently asked questions
How much does a Bailey Island holiday package cost?
You can grab a holiday package to this top destination on Expedia. But how much your holiday to Bailey Island costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Bailey Island?
Travel in the off-season and you're likely to find cheap Bailey Island holiday packages. Bear in mind that public holidays and major festivals and events can impact prices, so do your research before you go.
How many days is enough for Bailey Island?
You can explore all the leading sights in Bailey Island within a few days, including the must-see Land's End Gift Shop. If you're looking for a longer Bailey Island holiday, look at what sort of activities and day trips are available close by.
Is it worth booking a holiday package to Bailey Island?
Well known for its walking trails and home to leading attractions like Cobwork Bridge, a Bailey Island holiday is bound to impress. Another top sight to check out? Don't miss Bailey Island Bridge.
How to find the best Bailey Island package deals?
Use Expedia's filter tool to find some of the best Bailey Island package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Bailey Island package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your holiday package well in advance.
Is it cheaper to book a Bailey Island holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalised Bailey Island holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Bailey Island?
Secure incredible discounts by booking your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Bailey Island getaway.
How to plan a trip to Bailey Island?
- Choose your travel dates: The things you'd like to do in Bailey Island and your preferred season will help you decide when to travel.
- Set your budget: Factor in costs like flights, transportation and food when calculating how much to set aside for your trip to Bailey Island. Then, pick a hotel that works with your budget, whether that's an affordable option or a lavish retreat.
- Decide how long to go for: Now that you're up to speed on Bailey Island, you can work out the right length of your holiday. Pull together a draft itinerary and allocate enough time to get through everything on your must-do list.
- Combine your airfare and accommodation: After you've nailed down your dates and duration, lock in the perfect Bailey Island holiday package for you.
Explore a world of travel with Expedia
- Alfred Hotels
- Arundel Hotels
- Auburn Hotels
- Bath Hotels
- Popham Beach Direct Oceanfront Cottage Steps to the sand
- The Brunswick Hotel
- B&B in Brunswick
- Accor Hotels in Brunswick
- Brunswick Hotels
- Cottages in Cape Elizabeth
- Nature Lover’s Retreat on Thompson Lake – Cozy Cottage Escape
- Chelsea Hotels
- Houseboats in Chelsea
- Cundys Harbor Hotels
- Chalets in Edgecomb
- Friendship Hotels
- Gardiner Hotels
- Hostels in Gray
- Bufflehead Hideaway
- Kennebunk Hotels
- Litchfield Hotels
- Lakefront Midcoast Maine retreat
- Ocean Park Hotels
- Grand Victorian Oceanview 2BR/2BA Condo Steps to Beach
- La Quinta Inn & Suites Hotels in Old Orchard Beach
- Otisfield Hotels
- Oxford Hotels
- Cozy Maine Cottage
- The Porthole
- Caravan Parks in Poland
- Wyndham Hotels in Poland
- Poland Hotels
- Cabin Rentals in Portland
- Accor Hotels in Portland
- Aloft by Marriott Portland Downtown Waterfront ME
- Holiday Inn Portland
- Hyatt Place Portland Downtown
- Inn By The Sea
- Moby Dick Motel
- Old parsonage B&B
- Pet Friendly Hotels in Portland
- Pine View Lodge
- Seabreeze Motel
- The Boathouse Waterfront Hotel & Marina
- The Colony Hotel
- Portland Hotels
- Pet Friendly Hotels in Scarborough
- Sebago Hotels
- Cozy
- Southport Hotels
- B&B in Wales
- Houseboats in Walpole
- Apartments in Windham
- B&B in Windham
- Rise & Shine
- Windham Hotels
- Flights to Auburn
- Flights to Brunswick
- Flights to Kennebunkport
- Flights to Old Orchard Beach
- Flights to Portland
- Flights to Woolwich
- Flights from Portland Intl. Jetport
- Flights from Adelaide (ADL) to Portland (PWM)
- Flights from Brisbane (BNE) to Portland (PWM)
- Flights from Boston (BOS) to Portland (PWM)
- Flights from Buffalo (BUF) to Portland (PWM)
- Flights from Washington (DCA) to Portland (PWM)
- Flights from Dallas (DFW) to Portland (PWM)
- Flights from Devonport (DPO) to Portland (PWM)
- Flights from Newark Liberty Intl. Airport (EWR) to Portland (PWM)
- Flights from Honolulu (HNL) to Portland (PWM)
- Flights from New York (JFK) to Portland (PWM)
- Flights from Los Angeles (LAX) to Portland (PWM)
- Flights from New York (LGA) to Portland (PWM)
- Flights from Melbourne (MEL) to Portland (PWM)
- Flights from Miami (MIA) to Portland (PWM)
- Flights from Sydney (SYD) to Portland (PWM)
- Flights from Toowoomba (TWB) to Portland (PWM)
- Flights from Québec (YQB) to Portland (PWM)
- Flights from Toronto (YYZ) to Portland (PWM)
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
