Bailey's Bay Packages (Flight + Hotel)

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Top hotels in Bailey's Bay

Hamilton Princess & Beach Club - A Fairmont Hotel

Hamilton Princess & Beach Club - A Fairmont Hotel

4.5 out of 5
76 Pitts Bay Road Pembroke Parish
Fully refundableReserve now, pay when you stay
The price is ฿26,789 per night from 2 Aug to 3 Aug
฿26,789
฿31,127 total
2 Aug - 3 Aug
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"The staff at The Hamilton is top notch but the room this time was a real disappointment. This is our third time visiting within 12 months. We have always booked the Fairmont Gold Room. Previously we have had wonderful balcony rooms with beautiful views. This time we were given a room overlooking ..."

Reviewed on 7 Jul 2026

Hamilton Princess & Beach Club - A Fairmont Hotel
Grotto Bay Beach Resort

Grotto Bay Beach Resort

4 out of 5
11 Blue Hole Hill Hamilton Parish
The price is ฿22,130 per night from 14 Jul to 15 Jul
฿22,130
฿25,595 total
14 Jul - 15 Jul
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Our first trip to Bermuda & all was excellent! We stayed at the Grotto Bay Resort & did the all inclusive plan. It was so worth the expense as 3 delicious meals per day & all the drinks included (alcoholic as well). All the employees went above & beyond to make our stay exceptional! The wait staff ..."

Reviewed on 6 Jul 2026

Grotto Bay Beach Resort
Azura Bermuda

Azura Bermuda

4 out of 5
90 South Road Warwick Parish Warwick Parish
The price is ฿25,481 per night from 7 Aug to 8 Aug
฿25,481
฿31,850 total
7 Aug - 8 Aug
includes taxes & fees
9.4/10 Exceptional! (397 reviews)
"everything was perfect"

Reviewed on 4 Jul 2026

Azura Bermuda
See all 266 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.

Stay near popular Bailey's Bay attractions

Bermuda Perfumery

8.6/10 (172 reviews)
You can spend time browsing the exhibits at Bermuda Perfumery in Bailey's Bay. Wander through the beautiful beaches and seaside in this relaxing area.
See properties

What to do in Bailey's Bay

Bermuda Highlights Tour

Bermuda Highlights Tour

฿2,300
per adult
Bermuda Highlights Tour
Crystal Caves, Hamilton Shopping and Beach Tour

Crystal Caves, Hamilton Shopping and Beach Tour

฿4,928
per adult
92% of travellers recommend
Crystal Caves, Hamilton Shopping and Beach Tour
Bermudaful Island Beach Hop

Bermudaful Island Beach Hop

฿4,928
per adult
Bermudaful Island Beach Hop
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.

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