Enterprise Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Enterprise Vacation

Lock in a Enterprise vacation package and get ready to experience the best of this lively city. Consider staying in the neighborhood of Foul Bay, which is great for coastal beaches, watersports and nature. Fill your days with tours of Miami Beach, Oistins Friday Night Fish Fry and Christ Church Parish Church, some of the top attractions you shouldn't miss during a trip to Enterprise. Don't delay your visit to this destination any longer. The perfect Enterprise vacation is just a few clicks away with Expedia.

Enterprise Beach Vacation

Get ready to live out your beach fantasies on your upcoming Enterprise vacation. Go on a romantic walk, soak up the sparkling ocean views and pick up pretty seashells during your trip to Enterprise. Only 0.97 kilometres from the city center, Miami Beach is the place to be for many travelers. Look through our Enterprise vacation packages and watch your travel budget stretch further!

Ready to book your vacation to Enterprise?

 

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Enterprise Hotel Deals

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort

5 out of 5
End of Belair Road Long Bay St. Philip
Fully refundableReserve now, pay when you stay
The price is CA $698 per night from Jul 14 to Jul 15
CA $698
CA $782 total
Jul 14 - Jul 15
includes taxes & fees
7.8/10 Good! (707 reviews)
"My family and I took some time to choose the resort we wanted to stay on the island. The island is very safe and beautiful to explore outside of resort as well. The hotel is very clean, has some amazing staff that went above and beyond during our stay that we would like to shout out - Cashka and ..."

Reviewed on Jun 24, 2026

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort
Hilton Grand Vacations Club The Crane Barbados

Hilton Grand Vacations Club The Crane Barbados

4.5 out of 5
The Crane Resort Diamond Valley
Fully refundable
The price is CA $204 per night from Jul 27 to Jul 28
CA $204
CA $258 total
Jul 27 - Jul 28
includes taxes & fees
8.6/10 Excellent! (578 reviews)
"Was great with clean room and decent food and friendly staff"

Reviewed on Jun 28, 2026

Hilton Grand Vacations Club The Crane Barbados
Hilton Barbados Resort

Hilton Barbados Resort

4.5 out of 5
Needhams Point Bridgetown
Fully refundableReserve now, pay when you stay
The price is CA $399 per night from Jul 24 to Jul 25
CA $399
CA $493 total
Jul 24 - Jul 25
includes taxes & fees
8.4/10 Very good! (1,006 reviews)
"Overall great experience and service"

Reviewed on Jun 30, 2026

Hilton Barbados Resort
See all 3,479 properties in Enterprise
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Enterprise

Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise

Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise

CA $118
per adult
96% of travellers recommend
Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise
Atlantis Submarine Day Tour

Atlantis Submarine Day Tour

CA $163
per adult
92% of travellers recommend
Atlantis Submarine Day Tour
Luxury Evening Voyage - All-Inclusive Coastal Cruise By Oceanluxx

Luxury Evening Voyage - All-Inclusive Coastal Cruise By Oceanluxx

CA $145
per adult
100% of travellers recommend
Luxury Evening Voyage - All-Inclusive Coastal Cruise By Oceanluxx
See all activities in Enterprise

Frequently asked questions

How much does an Enterprise vacation package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a vacation to Enterprise costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Enterprise?
To score cheap Enterprise vacation packages, plan your getaway outside of peak times like public holidays and major events. You'll generally find lower prices and better availability for hotels and flights.
How many days is enough for Enterprise?
We recommend booking an Enterprise vacation for around 4 days. This will give you time to check off popular sights including Christ Church Parish Church and Ride The Tide Surf School Barbados, and explore neighbourhoods like Welches and Keizer Hill. You could even squeeze in a day trip or two from Enterprise.
How to find the best Enterprise package deals?
Use Expedia's handy filters to help you find some tempting Enterprise package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Enterprise package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book an Enterprise vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Enterprise vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Enterprise?
Score incredible discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Enterprise trip.
How to plan a trip to Enterprise?

  1. Choose your travel dates: What you want to do in Enterprise and your preferred season can help you decide when to travel.
  2. Set a budget: Factor in costs like food, flights and transportation when working out how much to set aside for your trip to Enterprise. Then, choose a property that matches your budget, whether that's an economical option or a more luxurious getaway.
  3. Work out your trip length: Consider how much time you'd like to spend discovering Enterprise. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose an Enterprise vacation package that brings all your bookings together.

Explore a world of travel with Expedia

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