Enterprise Holidays

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    Save up to S$134 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Enterprise Beach Holiday

Get ready to live out your beach fantasies on your upcoming Enterprise holiday. 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 centre, Miami Beach is the place to be for many travellers. Look through our Enterprise holiday packages and watch your travel budget stretch further!

Top hotels in Enterprise

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 S$934 per night from 19 Jan to 20 Jan
S$934
includes taxes & fees
19 Jan - 20 Jan
8/10 Very Good! (284 reviews)
"The food and staff at this resort was amazing. I really appreciated the hospitality here. Everything was great. The only thing this resort lacked was entertainment during the day. As well as there being no swim up bar :( once those two factors have been added in this resort would be 10/10 for ..."

Reviewed on 1 Jan,2025

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort
The Crane Resort
The Crane Resort
4.5 out of 5
Crane, Diamond Valley, St. Philip
Fully refundableReserve now, pay when you stay
The price is S$960 per night from 11 Jan to 12 Jan
S$960
includes taxes & fees
11 Jan - 12 Jan
8.4/10 Very Good! (1,002 reviews)
"the staff was friendly. The restaurants could have more local Bajan food.we ate out all the time. the property is well maintained, the team is very friendly"

Reviewed on 26 Dec,2024

The Crane Resort
Hilton Barbados Resort
Hilton Barbados Resort
4.5 out of 5
Needhams Point, Bridgetown
Fully refundableReserve now, pay when you stay
The price is S$620 per night from 7 Jan to 8 Jan
S$620
includes taxes & fees
7 Jan - 8 Jan
8.2/10 Very Good! (1,000 reviews)
"Nice place"

Reviewed on 25 Dec,2024

Hilton Barbados Resort
See all 3,465 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.

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.

What to do in Enterprise

Oistins

Experience Coastal Oistins

S$41
per adult
Experience Coastal Oistins
Beginner Surf Lesson in Barbados

Beginner Surf Lesson in Barbados

S$150
per adult
Beginner Surf Lesson in Barbados
Friday Night Live in Barbados

Friday Night Live in Oistins Private Tour

S$421
per adult
Friday Night Live in Oistins Private Tour
See all activities in Enterprise

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.