Bailey's Bay Vacations from $1,235

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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
Save 100% on your flight
Price was $1,729, price is now $1,235 per person
$1,235
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. George's (BDA)
9.2/10 Wonderful! (178 reviews)
Everything about this property is wonderful except for the hill. The cottages are beautifully clean and look brand new inside. The view of the harbour is stunning. The property is peaceful. The staff is warm and welcoming and helpful in every way. The only issues we had were the hill from the main street and the village of St. George's up to the hotel, the lack of a beach shuttle because it is only seasonal and the lack of a restaurant property because it is under renovation currently.

Reviewed on Mar 19, 2026

Azura Bermuda

Azura Bermuda

4 out of 5
Save 100% on your flight
Price was $3,235, price is now $2,198 per person
$2,198
per person
May 20 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. George's (BDA)
9.2/10 Wonderful! (342 reviews)
This is an excellent hotel in Bermuda with breathtaking views of the ocean.

Reviewed on Apr 6, 2026

Rosedon Hotel

Rosedon Hotel

4 out of 5
Save 100% on your flight
Price was $2,766, price is now $1,908 per person
$1,908
per person
May 20 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. George's (BDA)
9.8/10 Exceptional! (350 reviews)
The room was clean and the staff went out of their way to help. They also remembered our names and had great conversations with us dueing kurbstay

Reviewed on Mar 4, 2026

Cambridge Beaches Resort & Spa

Cambridge Beaches Resort & Spa

4 out of 5
Save 100% on your flight
Price was $3,359, price is now $2,446 per person
$2,446
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. George's (BDA)
9.2/10 Wonderful! (1,001 reviews)
Clean rooms. Friendly staff.

Reviewed on Mar 19, 2026

Newstead Belmont Hills Golf Resort & Spa

Newstead Belmont Hills Golf Resort & Spa

4 out of 5
Save 100% on your flight
Price was $4,738, price is now $3,577 per person
$3,577
per person
Jun 7 - Jun 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. George's (BDA)
9/10 Wonderful! (591 reviews)
Not a great atmosphere at front desk, some staff better than others. Pool area nice. Restaurants all nice. Shuttle drives great.

Reviewed on Apr 2, 2026

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

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 seaside, or simply savor its seafood restaurants.

Bermuda Aquarium Museum and Zoo (BAMZ)
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

Crystal Caves

4.5/5(195 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

What to do in Bailey's Bay

Bermuda Sights, Shopping & Sand Experience

Bermuda Sights, Shopping & Sand Experience

$70
per adult
Bermuda Sights, Shopping & Sand Experience
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 Shops, Sights and Shores Tour

Bermuda Shops, Sights and Shores Tour

$79
per adult
Bermuda Shops, Sights and Shores 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! (12 reviews)
Room was clean, food & fruit were appreciated. A few Kuerig coffees would have been good. Was quite windy during stay an window shutters made noise at night. TV internet connection kept disconnecting which was rating. Right faucet in bathroom doesn’t work. More information on Cottage location would ...

Reviewed on Oct 17, 2025

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Wyndham Water Views
Coco Reef Bermuda

Coco Reef Bermuda

3.5 out of 5
3 Stonington Circle Paget Parish
$370 nightly
The price is $408 total per night from Apr 7 to Apr 8
$408 total
Apr 7 - Apr 8
Total with taxes and fees
8.4/10 Very Good! (1,006 reviews)
Not a 5* hotel but it was everything it advertised and thus gave it 5*. I was not disappointed. It’s an older hotel that’s been updated. I was happy with the room. Great ocean view and left balcony doors open for the breeze. Ate at the restaurant for lunch, good. Used the beach, lovely. Walked to ...

Reviewed on Apr 3, 2026

Coco Reef Bermuda
Grotto Bay Beach Resort

Grotto Bay Beach Resort

4 out of 5
11 Blue Hole Hill Hamilton Parish
$455 nightly
The price is $511 total per night from Apr 15 to Apr 16
$511 total
Apr 15 - Apr 16
Total with taxes and fees
9/10 Wonderful! (1,003 reviews)
Lack of ambiance

Reviewed on Apr 3, 2026

Grotto Bay Beach 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.

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 $1,235 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.