Enterprise Vacations

Book a Hotel + Flight together to unlock savings

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    Better together

    Save up to AED 148 when you book a flight and hotel together*
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    Find the right fit

    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

Find the Best Enterprise Vacation Packages

Enterprise Hotel Deals

Hilton Barbados Resort

Hilton Barbados Resort

4.5 out of 5
Needhams Point, Bridgetown
Fully refundableReserve now, pay when you stay
The price is AED 995 per night from Sep 9 to Sep 10
AED 995
AED 1,230 total
9 Sep - 10 Sep
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"I was very disappointed when the cleaner left dirtynpaper on the bed head"

Reviewed on 15 August 2025

Hilton Barbados Resort
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 AED 1,663 per night from Aug 21 to Aug 22
AED 1,663
AED 1,865 total
21 Aug - 22 Aug
includes taxes & fees
7.6/10 Good! (467 reviews)
"I love the friendly staff, and how attentive the staff is to your needs.The place is very clean,very beautiful.The rooms are clean and cold,the pools are lovely n relaxing. The food and drinks are out of this world.I took my daughter there from 2nd August til the 3rd, and she love it soon much that ..."

Reviewed on 14 August 2025

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort
Sugar Bay Barbados - All Inclusive

Sugar Bay Barbados - All Inclusive

4 out of 5
Garrison Historic Area, Hastings
The price is AED 2,373 per night from Aug 19 to Aug 20
AED 2,373
AED 2,816 total
19 Aug - 20 Aug
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
"Sugar Bay is beautiful. It's quiet and smaller than super-resorts. The food was good - Sizzler steakhouse was outstanding. Getting to the hotel and accessing excursions was easy. Staff was friendly and accommodating. Would highly recommend."

Reviewed on 16 August 2025

Sugar Bay Barbados - All Inclusive
See all 3,449 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

Miami Beach featuring a sandy beach and landscape views

Miami Beach

Nothing says vacation like spending a lazy day at Miami Beach, a popular beach in Oistins. While you're here, you can savor the top-notch restaurants.

Miami Beach

Oistin's Friday Night Fish Fry

Enjoy a stop at Oistin's Friday Night Fish Fry, an entertaining place to visit in Scarborough. Discover the area's beautiful sunsets and seafood restaurants.

Oistin's Friday Night Fish Fry

Christ Church Parish Church

You can find out about the history of Scarborough with a stop at Christ Church Parish Church. Stroll along the beautiful beaches or discover the area's beautiful sunsets.

Christ Church Parish Church

Frequently asked questions

How much does an Enterprise vacation package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a vacation 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 vacation packages? Try to avoid visiting during public holidays and any major festivals.
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 vacation package well in advance.
Is it cheaper to book an Enterprise vacation as a package?
An Expedia vacation 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 vacation package to Enterprise?
If you've got your Enterprise vacation 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 accommodations, 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 accommodations: Once you've nailed down your trip dates and duration, lock in the ideal Enterprise vacation package for you.