Bailey Island Holidays

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Bailey Island Holiday

Our pick of the best Bailey Island Hotel Deals

BAILEY ISLAND MOTEL
BAILEY ISLAND MOTEL
2 out of 5
2041 Harpswell Islands Rd, Bailey Island, ME
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BAILEY ISLAND MOTEL
La Quinta Inn & Suites by Wyndham Portland
La Quinta Inn & Suites by Wyndham Portland
3 out of 5
340 Park Ave, Portland, ME
The price is NZ$313 per night from 30 June to 1 July
NZ$313
30 June - 1 July
includes taxes & fees
8.8/10 Excellent! (2,178 reviews)
"Very nice hotel, more updated than some others I've stayed at in the rea, staff was pleasant and friendly."

Reviewed on 24 Jun. 2025

La Quinta Inn & Suites by Wyndham Portland
Hyatt Place Portland Downtown - Old Port Square
Hyatt Place Portland Downtown - Old Port Square
3 out of 5
433 Fore St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is NZ$442 per night from 6 July to 7 July
NZ$442
6 July - 7 July
includes taxes & fees
8.8/10 Excellent! (1,145 reviews)
"The location is perfect for a day in the city. Close to everything. The staff was friendly. The free shuttle to the airport was easy to arrange with the service offered 24 hours. I was transported at 3:20 am to the airport saving the cost of an Uber and assured safety at the hour. The gym was under ..."

Reviewed on 23 Jun. 2025

Hyatt Place Portland Downtown - Old Port Square
See all 1,795 properties in Bailey Island
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.

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?

  1. 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.
  2. 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.
  3. 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.
  4. Combine your airfare and accommodation: After you've nailed down your dates and duration, lock in the perfect Bailey Island holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.