Bailey's Bay Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ￥45,448 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

Find the Best Bailey's Bay Vacation Packages

Bailey's Bay Hotel Deals

Paradise at Limehouse

Paradise at Limehouse

Hamilton
The price is ￥22,226 per night from Aug 23 to Aug 24
￥22,226
￥33,854 total
Aug 23 - Aug 24
includes taxes & fees
9.4/10 Exceptional! (38 reviews)
"The accomodation was exactly as described, it was very conveniently located near a bus stop to get anywhere on the island. It was within walking distance of a market, Crystal/ fantasy caves, and Swizzle Inn. The host, Goodwin was helpful and responsive. The AC worked great! I would stay again."

Reviewed on Jul 18, 2025

Paradise at Limehouse
Manders Estate Ocean View Bed & Breakfast - Wake Up to Paradise

Manders Estate Ocean View Bed & Breakfast - Wake Up to Paradise

Hamilton
Get rates
Manders Estate Ocean View Bed & Breakfast - Wake Up to Paradise
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 ￥102,886 per night from Sep 1 to Sep 2
￥102,886
￥128,801 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (227 reviews)
"Nice hotel clean and very attentive staff nice beach and pool areas"

Reviewed on Aug 14, 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.

Discover the most popular places to visit in Bailey's Bay

Flatts sunset view

Bermuda Aquarium Museum and Zoo (BAMZ)

Make time to visit the sea animals who live in Bermuda Aquarium Museum and Zoo (BAMZ) during your trip to Hamilton Parish. Stroll along the area's beautiful beaches, or simply savor its top-notch restaurants.

Bermuda Aquarium Museum and Zoo (BAMZ)

What to do in Bailey's Bay

Make the Most of Your Time Together!

East End Excursion: Private Guided Family Tour in Bermuda

￥14,031
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

￥20,677
per adult
94% of travellers recommend
Crystal Caves, Hamilton Shopping and Beach Tour
Bermuda Island Tour

Bermuda Island Tour

￥27,323
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 vacation package cost?
You can grab a vacation package to this top destination on Expedia. However, how much your vacation 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 vacation 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 vacation. 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 vacation package as early as possible.
Is it cheaper to book a Bailey's Bay vacation as a package?
Expedia vacation 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 vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation 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 favorite season and the activities on offer will also help you decide when to vacation 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 accommodations: Once you've nailed down your travel dates and duration, book the ideal Bailey's Bay vacation package for you.

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