Bailey's Bay Holidays

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Top hotels in Bailey's Bay

Grotto Bay Beach Resort

Grotto Bay Beach Resort

4 out of 5
11 Blue Hole Hill, Bailey's Bay, Hamilton Parish
The price is S$693 per night from 4 Sept to 5 Sept
S$693
4 Sept - 5 Sept
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Beautiful"

Reviewed on 24 Aug, 2025

Grotto Bay Beach Resort
Hamilton Princess & Beach Club - a Fairmont Managed Hotel

Hamilton Princess & Beach Club - a Fairmont Managed Hotel

4.5 out of 5
76 Pitts Bay Road, Pembroke Parish
Fully refundableReserve now, pay when you stay
The price is S$711 per night from 28 Sept to 29 Sept
S$711
28 Sept - 29 Sept
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"The staff is awesome! They are extremely helpful, reliable, knowledgeable and kind. The gold check-in is worth it. They are continuing to renovate the hallways which is a plus. I wish you could book excursion bookings from the front desk."

Reviewed on 22 Aug, 2025

Hamilton Princess & Beach Club - a Fairmont Managed Hotel
The St. Regis Bermuda Resort

The St. Regis Bermuda Resort

5 out of 5
34 Coot Pond Road, Town of St. George
The price is S$1,048 per night from 22 Sept to 23 Sept
S$1,048
22 Sept - 23 Sept
includes taxes & fees
9/10 Wonderful! (235 reviews)
"excellent in every respect... except you can't get anything to eat between 11&noon."

Reviewed on 26 Aug, 2025

The St. Regis Bermuda Resort
See all 272 properties in Bailey's Bay
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.

What to do in Bailey's Bay

Make the Most of Your Time Together!

East End Excursion: Private Guided Family Tour in Bermuda

S$122
per adult
East End Excursion: Private Guided Family Tour in Bermuda
Crystal Caves, Hamilton Shopping and Beach Tour

Crystal Caves, Hamilton Shopping and Beach Tour

S$180
per adult
94% of travellers recommend
Crystal Caves, Hamilton Shopping and Beach Tour
Bermuda Island Tour

Bermuda Island Tour

S$238
per adult
100% of travellers recommend
Bermuda Island Tour
See all activities in Bailey's Bay

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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.