Bailey Island Holidays

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Top hotels in Bailey Island

Portland Harbor Hotel
Portland Harbor Hotel
4 out of 5
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is S$244 per night from 23 Feb to 24 Feb
S$244
includes taxes & fees
23 Feb - 24 Feb
9/10 Wonderful! (1,456 reviews)
5 stars
"This is my second time staying here. I am a Chef and I go up in the Winter to go to all of my favorite restaurants. This hotel is in the best location to get to so many great locations. The staff is extremely friendly, and helpful. The breakfast was so good i got it 3 days in a row. I cant wait to ..."

Reviewed on 3 Feb,2025

Portland Harbor Hotel
Holiday Inn Portland-By the Bay, an IHG Hotel
Holiday Inn Portland-By the Bay, an IHG Hotel
3 out of 5
88 Spring St, Portland, ME
Fully refundable
The price is S$146 per night from 9 Feb to 10 Feb
S$146
includes taxes & fees
9 Feb - 10 Feb
8.8/10 Excellent! (1,140 reviews)
"Great modern super clean rooms . Super close to all things we wanted to do . Great water view from our room"

Reviewed on 4 Feb,2025

Holiday Inn Portland-By the Bay, an IHG Hotel
Cambria Hotel Portland Downtown-Old Port
Cambria Hotel Portland Downtown-Old Port
3 out of 5
25 HANCOCK STREET, Portland, ME
Fully refundableReserve now, pay when you stay
The price is S$181 per night from 17 Feb to 18 Feb
S$181
includes taxes & fees
17 Feb - 18 Feb
9.2/10 Wonderful! (761 reviews)
"Love everything about this hotel. The room. The convenience to the Old Port. The food. Brunch was delicious."

Reviewed on 3 Feb,2025

Cambria Hotel Portland Downtown-Old Port
See all 1,605 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.