Bailey's Bay Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 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
Top hotels in Bailey's Bay
Hamilton Princess & Beach Club - A Fairmont Hotel
76 Pitts Bay Road Pembroke Parish
Fully refundableReserve now, pay when you stay
S$903
12 Sept - 13 Sept
includes taxes & fees
9.2/10 Wonderful! (1,010 reviews)
"Perfect vacation! Great location, amazing food and fantastic service. We will be back!"
Reviewed on 26 Aug, 2026
Grotto Bay Beach Resort
11 Blue Hole Hill Hamilton Parish
S$690
10 Sept - 11 Sept
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"I liked everything about this hotel, the all inclusive option was excellent, the staff was amazing and very helpful especially the capitana at the Pearl and Hibiscus, I don’t remember their names but all of them are just amazing and welcoming 😊 all the staff at the beach bar were amazing as well ..."
Reviewed on 26 Aug, 2026
The St. Regis Bermuda Resort
34 Coot Pond Road Town of St. George
S$1,186
21 Sept - 22 Sept
includes taxes & fees
9.2/10 Wonderful! (349 reviews)
"Unbelievably beautiful!"
Reviewed on 26 Aug, 2026
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's Bay attractions
Abbot's Cliff Park
8.8/10 (10 reviews)
Explore the lovely green spaces of Abbot's Cliff Park and enjoy the golf courses in Bailey's Bay. Amble around this family-friendly area's beautiful beaches and enjoy its top-notch restaurants.
What to do in Bailey's Bay
Bermuda Discovery & Highlights with FREE Scenic Ferry Return
S$96
per adult
Crystal Cave, St. George and Tobacco Bay Beach
S$192
per adult
Frequently asked questions
How much does a Bailey's Bay holiday package cost?
You can grab a holiday package to this top destination on Expedia. However, how much your holiday to Bailey's Bay costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Bailey's Bay?
To pick up cheap Bailey's Bay holiday packages, plan your getaway outside of peak periods like public holidays and major festivals. You'll generally find lower prices and better availability for hotels and flights.
How many days is enough for Bailey's Bay?
Typically, a handful of days is enough to check out the main sights during your Bailey's Bay holiday. However, if you'd like to have some time to chill out or take day tours, consider extending your trip.
How to find the best Bailey's Bay package deals?
Use Expedia's filter tool to help you find some fabulous Bailey's Bay package deals. When you start your search, just 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 look for Bailey's Bay package deals in the off-peak 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 as early as possible.
Is it cheaper to book a Bailey's Bay holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Bailey's Bay holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday package to Bailey's Bay?
Enjoy incredible bargains by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Bailey's Bay escape.
How to plan a trip to Bailey's Bay?
- Choose when to get away: Check your calendar and pack your bags. Your favourite season and the activities on offer will also help you decide when to holiday in Bailey's Bay.
- Plan your budget wisely: On top of the cost of your hotel, you should consider other expenses. These include food, transportation and flights. Also, set aside some extra funds for unexpected expenses that could arise during your trip to Bailey's Bay.
- Decide how many days away: Start by making a list of all the activities and sights you want to get to in Bailey's Bay. Then, estimate how long you'll need at each, as well as any travel time.
- Combine your airfare and accommodation: Once you've nailed down your travel dates and duration, book the ideal Bailey's Bay 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.
