Bailey's Bay Vacations from $1,254

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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

Save 100% on your flight
$1,254
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. George's (BDA)
9.2/10 Wonderful! (200 reviews)
Azura Bermuda

Azura Bermuda

Save 100% on your flight
$1,499
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. George's (BDA)
9.4/10 Exceptional! (440 reviews)
Beautiful big private beach. Staff is kind a very friendly. Pool is small and inside the outdoor area of the restaurant. Beautiful rooms with full kitchen washer, dryer and big ocean front balcony. Hamilton area is 10-15 mins by taxi. We are a family of 4 and taxi or public transportation was the only choice we had for getting around. There is really no walking outside the resort area. The roads don’t have sidewalks right outside the resort and there are one gas station convenience store and one restaurant 10 mins walk. It’s a beautiful resort but I wish we had an option for a rental car. Also every night and throughout the morning there are noisy whistling frogs the are hard to get used to.

Reviewed on Aug 25, 2026

Hamilton Princess - Fairmont Gold Experience

Hamilton Princess - Fairmont Gold Experience

Save 100% on your flight
$4,841
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. George's (BDA)
9.2/10 Wonderful! (60 reviews)
The staff was excellent! Super friendly and helpful. The room we had was beautiful.

Reviewed on Aug 20, 2026

Cambridge Beaches Resort & Spa

Cambridge Beaches Resort & Spa

Save 100% on your flight
$1,892
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. George's (BDA)
9.2/10 Wonderful! (1,004 reviews)
Newstead Belmont Hills Golf Resort & Spa

Newstead Belmont Hills Golf Resort & Spa

Save 100% on your flight
$1,952
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. George's (BDA)
9/10 Wonderful! (616 reviews)
Our stay at this resort was comfortable and very relaxing. I would like to return one day. The room and grounds were beautiful, clean and quiet. The food was expensive, among other things, but delicious. However, our room had a full kitchen so we got to make use of it some days. A supermarket is accessible closeby or you can have groceries delivered. The resort's complimentary ferry was also a plus to explore the beautiful city of Hamilton. A free shuttle to the beach is also available. I would suggest that the Resort include some family friendly activities for guests like scaveger hunts by the beautiful grounds, a kid's corner or a club for different age groups and Karaoke night by the pool to add to the experience. I believe that a calendar with these types of activities would be well received by guests with children as well as couples. The resort offers yoga classes and pool aerobics both for a fee. There is a table to play ping pong by the pool but I never saw anyone using it. Add a calendar of activities, that are included with the stay, to the website, guest rooms or give a copy upon arrival.

Reviewed on Aug 25, 2026

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Stay near popular Bailey's Bay attractions

Abbot's Cliff Park

8.8/10 (10 reviews)
Explore the lovely green spaces of Abbot's Cliff Park and enjoy the golf courses in Bailey's Bay. Amble around this family-friendly area's beautiful beaches and enjoy its top-notch restaurants.
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What to do in Bailey's Bay

Bermuda Shipwreck Snorkel

Shipwreck Snorkel in Bermuda

$105
per adult
100% of travellers recommend
Shipwreck Snorkel in Bermuda
Bermuda Sights, Shopping & Sand Experience

Bermuda Sights, Shopping & Sand Experience

$65
per adult
Bermuda Sights, Shopping & Sand Experience
Bermudaful Island Caves and Coastlines Tour

Bermudaful Island Cave and Coastlines Tour

$115
per adult
Bermudaful Island Cave and Coastlines Tour
See all activities in Bailey's Bay

Bailey's Bay Hotel Deals

Wyndham Water Views

Wyndham Water Views

Hamilton Hamilton Parish
Wyndham Water Views
Hamilton Princess & Beach Club - A Fairmont Hotel

Hamilton Princess & Beach Club - A Fairmont Hotel

76 Pitts Bay Road Pembroke Parish
Fully refundableReserve now, pay when you stay
$637 nightly
$712 total
Sep 12 - Sep 13
Total with taxes and fees
Hamilton Princess & Beach Club - A Fairmont Hotel
Grotto Bay Beach Resort

Grotto Bay Beach Resort

11 Blue Hole Hill Hamilton Parish
$486 nightly
$544 total
Sep 8 - Sep 9
Total with taxes and fees
Grotto Bay Beach Resort
See all 271 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 $1,254 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.

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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.