Bailey's Bay Vacations from $1,085

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Your Baileys Bay Vacation

With a vacation package to Baileys Bay, say goodbye to travel planning and hello to stress-free adventure. Every detail of your journey has been taken care of before departing, so you can enjoy each moment discovering this interesting city. You'll want to take in some sights during your trip to Baileys Bay. Don't miss major attractions such as Bermuda Aquarium Museum and Zoo, Crystal Caves and Bermuda Perfumery. A couple of clicks is all it takes to build your dream Baileys Bay vacation on Expedia.

The Latest Bailey's Bay vacation packages

Price found within the past 48 hours. Click for updated prices.
St George's Club Hotel

St George's Club Hotel

2 out of 5
Price was $1,482, price is now $1,085 per person
$1,085
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. George's (BDA)
9.4/10 Exceptional! (184 reviews)
The resort was quiet and views outstanding. Restaurants, ferry boat, grocery store, busstop within a 10-min walk. Free shuttle van convenient to these areas plus to the beaches.

Reviewed on May 20, 2026

Coco Reef Bermuda

Coco Reef Bermuda

3.5 out of 5
Save 100% on your flight
Price was $2,459, price is now $1,617 per person
$1,617
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. George's (BDA)
8.4/10 Very Good! (1,001 reviews)
Being mid-island was perfect for us. We rented a moped for our 5 day stay, and traveled to Hamilton (which is very close), to St. George, and the Navy Dockyard. And having a private beach on the ocean side (rather than a bay) was awesome. The beach was never overcrowded during our stay. And the quality of the food at the in house restaurant was excellent.

Reviewed on May 24, 2026

Azura Bermuda

Azura Bermuda

4 out of 5
Save 100% on your flight
Price was $2,157, price is now $1,558 per person
$1,558
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. George's (BDA)
9.2/10 Wonderful! (368 reviews)
The staff was very nice and our room was beautiful. The weather was awful so that limited what we could do. The restaurant was very expensive and the food not very good. There’s really no beach either.

Reviewed on May 21, 2026

Cambridge Beaches Resort & Spa

Cambridge Beaches Resort & Spa

4 out of 5
Save 100% on your flight
Price was $1,749, price is now $1,277 per person
$1,277
per person
Jul 11 - Jul 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. George's (BDA)
9.2/10 Wonderful! (1,002 reviews)
El hambre te muy agradable, desde la habitación se puede apreciar la belleza de la playa, la habitación espaciosa y limpia lo único que se escucha lo de la habitación vecina, durante mi estadía se fue el agua dos veces en un solo día, el personal amable especialmente los botones, en general bonita experiencia.

Reviewed on May 23, 2026

The Loren at Pink Beach

The Loren at Pink Beach

5 out of 5
Save 100% on your flight
Price was $1,968, price is now $1,553 per person
$1,553
per person
Jul 11 - Jul 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. George's (BDA)
9.6/10 Exceptional! (269 reviews)
The most beautiful resort we’ve ever stayed at!

Reviewed on Apr 10, 2026

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

Crystal Caves, Bermuda

Crystal Caves

4.5/5(196 reviews)

Explore the lovely green spaces of Crystal Caves and enjoy the golf courses in Hamilton Parish. Amble around this relaxing area's beautiful beaches and enjoy its top-notch restaurants.

Crystal Caves
Blue Hole Park

Blue Hole Park

4/5(11 reviews)

Explore the lovely green spaces of Blue Hole Park and enjoy the golf courses in Hamilton Parish. Amble around this relaxing area's beautiful beaches and enjoy its top-notch restaurants.

Blue Hole Park
Bermuda Aquarium Museum and Zoo (BAMZ)

Bermuda Aquarium Museum and Zoo (BAMZ)

4.5/5(106 reviews)

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

Johnny!

Bermuda Shops, Sights and Shores Tour

$79
per adult
Bermuda Shops, Sights and Shores Tour
Crystal Caves, Hamilton Shopping and Beach Tour

Crystal Caves, Hamilton Shopping and Beach Tour

$150
per adult
92% of travellers recommend
Crystal Caves, Hamilton Shopping and Beach Tour
Bermuda Highlights Tour

Bermuda Highlights Tour

$70
per adult
Bermuda Highlights Tour
See all activities in Bailey's Bay

Bailey's Bay Hotel Deals

Wyndham Water Views

Wyndham Water Views

Hamilton Hamilton Parish
9/10 Wonderful! (14 reviews)
"Loved staying at this place. What a beautiful view from the top of the mountain. Comfy and clean. Can be difficult to find for pizza delivery and taxi drivers alike."

Reviewed on May 17, 2026

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Wyndham Water Views
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
$777 nightly
The price is $864 total per night from May 30 to May 31
$864 total
May 30 - May 31
Total with taxes and fees
9.2/10 Wonderful! (1,003 reviews)
"Would stay again here. Loved it."

Reviewed on May 25, 2026

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

Grotto Bay Beach Resort

4 out of 5
11 Blue Hole Hill Hamilton Parish
$566 nightly
The price is $636 total per night from May 27 to May 28
$636 total
May 27 - May 28
Total with taxes and fees
9/10 Wonderful! (1,008 reviews)
"We had a very pleasant stay after requesting we be moved to a less remote room with a better view. The staff was friendly, though we could not always get the information we needed. We were not on the all-inclusive plan and when we wanted a little breakfast we were told the dining room was only serving ..."

Reviewed on May 25, 2026

Grotto Bay Beach Resort
See all 280 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.

Find the Best Bailey's Bay Vacation Packages

Baileys Bay Essential Information

Language
English
Currency
Bermudian dollars
Closest Airport
L.F. Wade Intl. Airport (BDA)
Max Temp Winter
70ºF
Max Temp Summer
80ºF
Top Sights
Crystal Caves, Bermuda Aquarium Museum and Zoo and Blue Hole Park

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Frequently asked questions

How much does a Bailey's Bay vacation package cost?
You can grab a vacation package to this top destination from $1,085 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?
September, November and December are the best times to search for cheap Bailey's Bay vacation packages. Traveling in quieter months means you'll typically find better prices on hotels and flights.
How many days is enough for Bailey's Bay?
Typically, a handful of days is enough to go to the major attractions during your Bailey's Bay vacation. However, if you want to have time to chill out or go on day trips, think about 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 your dates: What you want to do in Bailey's Bay and your favorite season can help you decide when to travel.
  2. Set a budget: Factor in costs such as transportation, flights and meals when working out how much to put aside for your trip to Bailey's Bay. Then, pick a hotel that fits your budget, whether that's a low-cost stay or a lavish getaway.
  3. Use Expedia's trip planning tool to discover Bailey's Bay: Research every aspect of your trip to Bailey's Bay with this comprehensive planner. Invite your friends and family to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Decide how many days away: Start by making a list of all the sights and activities you'd like to get to in Bailey's Bay. Then, estimate how long you'll need for each, along with any travel time.
  5. Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to find a Bailey's Bay vacation package that brings all your bookings together.
  6. Add on experiences and excursions: Take a look at our dedicated travel guide to find some awesome things to do in Bailey's Bay. Book tickets or make reservations in advance to save time and skip the hassle of looking for activities once you arrive.

Does Expedia offer Book Now, Pay Later Bailey's Bay vacation packages?
If you're like us, you love exploring new places but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Bailey's Bay trip over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.