Enterprise Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to NZ$616 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

Enterprise Holiday

Our pick of the best 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 NZ$901 per night from 22 July to 23 July
NZ$901
22 July - 23 July
includes taxes & fees
7.6/10 Good! (445 reviews)
"Everything about the property was fantastic: The beach was the only negative, I still give it a 100% for everything else."

Reviewed on 15 Jul. 2025

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
The price is NZ$338 per night from 18 Aug to 19 Aug
NZ$338
18 Aug - 19 Aug
includes taxes & fees
8.2/10 Very Good! (330 reviews)
"All staff were outstanding and service and cleanliness was on point. A great stay!!! Coming back next year!!"

Reviewed on 18 Jul. 2025

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 NZ$497 per night from 5 Aug to 6 Aug
NZ$497
5 Aug - 6 Aug
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Everybody was more than nice every where you go."

Reviewed on 16 Jul. 2025

Hilton Barbados Resort
See all 3,466 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.

Discover the most popular places to visit in Enterprise

South Point Lighthouse

You can find out about the history of Oistins with a trip to South Point Lighthouse. Discover the area's entertainment choices or seek out its surfing spots.

South Point Lighthouse

What to do in Enterprise

Oistins

Experience Coastal Oistins

NZ$50
per adult
Experience Coastal Oistins
Flying Dress Photoshoot in Barbados

Flying Dress Photoshoot in Barbados

NZ$998
per adult
Flying Dress Photoshoot in Barbados
Friday Night Live in Barbados

Friday Night Live in Oistins Private Tour

NZ$516
per adult
Friday Night Live in Oistins Private Tour
See all activities in Enterprise

Frequently asked questions

How much does an Enterprise holiday package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Enterprise costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Enterprise?
The off-season is the best time to head to Enterprise if you're hoping to keep costs down. Another tip for scoring cheap Enterprise holiday packages? Try to avoid visiting during public holidays and any major festivals.
How many days is enough for Enterprise?
With a well-organised itinerary, you can easily visit the most popular Enterprise sights in a handful of days. But if you'd like to explore off the beaten track or go on day trips, consider booking your Enterprise holiday for longer.
How to find the best Enterprise package deals?
Use Expedia's filters to find some of the best 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 break for midweek, or browse for Enterprise package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your holiday package well in advance.
Is it cheaper to book an Enterprise holiday as a package?
An Expedia holiday package could score you significant savings when compared to arranging hotels and flights separately. Better still, you can tailor your Enterprise trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Enterprise?
If you've got your Enterprise holiday dates finalized, book as soon as you can to score some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Enterprise?

  1. Choose when to go: Check your schedule and get your bags packed. Your preferred season and the type of activities on offer will also help you decide when to visit Enterprise.
  2. Budget wisely: Besides the price of your accommodation, you'll need to factor in other expenses too. These include transportation, flights and food. Also, set aside some extra funds for unexpected costs that could arise during your trip to Enterprise.
  3. Set the duration of your trip: Start by making a list of all the activities and attractions you'd like to get to in Enterprise. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your airfare and accommodation: Once you've nailed down your trip dates and duration, lock in the ideal Enterprise holiday package for you.

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