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.

Top Enterprise Vacation Deals

Price found within the past 48 hours. Click for updated prices.
East Resort

East Resort

CA $925
per person
Oct 25 - Oct 30
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Bridgetown (BGI)
5/10 (2 reviews)
The Club, Barbados Resort & Spa Adults Only - All Inclusive

The Club, Barbados Resort & Spa Adults Only - All Inclusive

CA $1,555
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Bridgetown (BGI)
8/10 Very good! (553 reviews)
The rooms were clean. The staff was excellent. Provided great information on things that were happening off the resort arranged transportation to get there.

Reviewed on Aug 12, 2026

Sea Symphony Villa

Sea Symphony Villa

CA $1,020
per person
Oct 25 - Oct 30
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Bridgetown (BGI)
8.6/10 Excellent! (11 reviews)
Saint Peter's Bay

Saint Peter's Bay

CA $1,753
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Bridgetown (BGI)
9.6/10 Exceptional! (168 reviews)
Our unit was amazing & very clean. The staff was extreamly friendly. Great place to enjoy a peaceful vacation!

Reviewed on Jul 12, 2026

The Crane Resort

The Crane Resort

CA $1,240
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Bridgetown (BGI)
8.6/10 Excellent! (1,010 reviews)
First time at The Crane. I visit Barbados often, but usually stay with family. This time around i had a group of 6 including 3 children in my party so decided to stay at The Crane. The grounds are well maintained and everyone was very friendly and welcoming. We reserved 2 rooms. At check in my sister was upgrade given her party was 4. Her accommodations was located in the “ residence”. The room was absolutely breathtaking!! 3 bedrooms, balconies with a panoramic view of the ocean, the updated kitchen and baths were beautiful. Now, my party of 2 were placed in an older building. The room was comfortable, clean, but definitely dated with dark wood furniture. After a day we were also updated to a larger room within one of the older buildings. Well, unfortunately that room had some issues that we noted within minutes. We contacted the front desk and they came to inspect the room. The staff couldn’t have been nicer. Everyone from the front desk, evening manger and bell person was so helpful. We had another room within an hour and they had someone come and move us. The room was newly renovated and had a rooftop deck, pool and grill. Although we were happy with our first accommodations this room was exceptional! Hopefully they will continue to renovate the older units. They are doing an excellent job with the newer ones. The food was good and the drinks are strong! The Crane sour and Carnival sour were my favorites. I can’t say enough about the staff. I will definitely be back!

Reviewed on Aug 13, 2026

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?

Choose your dates

Enterprise Hotel Deals

Hilton Grand Vacations Club The Crane Barbados

Hilton Grand Vacations Club The Crane Barbados

The Crane Resort Diamond Valley
Fully refundable
CA $224
CA $282 total
Aug 17 - Aug 18
includes taxes & fees
Hilton Grand Vacations Club The Crane Barbados
Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort

End of Belair Road Long Bay St. Philip
Fully refundableReserve now, pay when you stay
CA $628
CA $706 total
Aug 21 - Aug 22
includes taxes & fees
Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort
The Crane Resort

The Crane Resort

Crane Diamond Valley St. Philip
Fully refundableReserve now, pay when you stay
CA $458
CA $573 total
Aug 21 - Aug 22
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"First time at The Crane. I visit Barbados often, but usually stay with family. This time around i had a group of 6 including 3 children in my party so decided to stay at The Crane. The grounds are well maintained and everyone was very friendly and welcoming. We reserved 2 rooms. At check in my sister ..."

Reviewed on Aug 13, 2026

The Crane Resort
See all 3,557 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.

What to do in Enterprise

Atlantis Submarine Day Tour

Atlantis Submarine Day Tour

CA $168
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 $147
per adult
100% of travellers recommend
Luxury Evening Voyage - All-Inclusive Coastal Cruise By Oceanluxx
Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise

Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise

CA $119
per adult
96% of travellers recommend
Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise
See all activities in Enterprise

Frequently asked questions

How much does an Enterprise vacation package cost?
Offering great value package deals from CA $925 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.