Travel to Bailey Island

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to RM 324 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Bailey Island

Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is RM632 per night from 20 Jul to 21 Jul
RM632
RM689 total
20 Jul - 21 Jul
includes taxes & fees
7.8/10 Good! (1,021 reviews)
"It was very clean and updated"

Reviewed on 16 Jul 2025

Days Inn by Wyndham Airport/Maine Mall
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is RM646 per night from 29 Jul to 30 Jul
RM646
RM715 total
29 Jul - 30 Jul
includes taxes & fees
7.8/10 Good! (1,026 reviews)
"Closely located to airport and local attractions and great food options"

Reviewed on 14 Jul 2025

Clarion Hotel Portland
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is RM610 per night from 20 Jul to 21 Jul
RM610
RM675 total
20 Jul - 21 Jul
includes taxes & fees
7.6/10 Good! (1,039 reviews)
Good and clean
"Good location for us and very convenient to all the areas nearby that we had to go. We enjoyed the quiet and were able to easily and quickly get additional towels and supplies as we needed."

Reviewed on 14 Jul 2025

Ramada Plaza by Wyndham Portland
See all 1,849 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.

Popular places to visit

Land's End Gift Shop

Enjoy an outing to Land's End Gift Shop during your stay in Bailey Island. While you're in the area, find time to visit its shops.

Land's End Gift Shop

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.