Enterprise Holidays

  • Plan, book, travel with confidence

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    Better together

    Save up to S$134 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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    Rest easy

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

Top hotels in Enterprise

Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
No 1 Wrighton Road, Port of Spain, Trinidad
Fully refundableReserve now, pay when you stay
The price is S$277 per night from 20 Aug to 21 Aug
S$277
20 Aug - 21 Aug
includes taxes & fees
9/10 Wonderful! (1,009 reviews)
"We enjoyed our stay. However, the wait time for orders in the restaurant is way too long. We experienced a wait time of at least 40 minutes before they began serving our food. Furthermore, the food was served in lengthy intervals: Some us were finished eating before others even got their food. Very ..."

Reviewed on 20 Jul, 2025

Hyatt Regency Trinidad
Hilton Trinidad & Conference Centre

Hilton Trinidad & Conference Centre

4.5 out of 5
Lady Young Road, Belmont, Port of Spain
Fully refundableReserve now, pay when you stay
The price is S$258 per night from 21 Aug to 22 Aug
S$258
21 Aug - 22 Aug
includes taxes & fees
8/10 Very Good! (1,006 reviews)
"Amazing staff . Convenient location . Beautiful scenery . The hotel itself needs a little TLC , its a little dated . A little dissapointed that the Cascadoo bar at the pool area was closed during my 3 day stay and the breakfast was very limited in the local cuisine . Bake with no saltfish or smoke ..."

Reviewed on 22 Jul, 2025

Hilton Trinidad & Conference Centre
Holiday Inn Express Hotel & Suites Trincity Trinidad Airport by IHG

Holiday Inn Express Hotel & Suites Trincity Trinidad Airport by IHG

3 out of 5
No 1 Exposition Drive, Piarco, Trinidad
Fully refundable
The price is S$222 per night from 21 Aug to 22 Aug
S$222
21 Aug - 22 Aug
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
Quick layover
"Hotel staff was especially nice; they provided a quick shuttle service to and from the airport. Breakfast was delicious. Definitely booking again."

Reviewed on 16 Jul, 2025

Holiday Inn Express Hotel & Suites Trincity Trinidad Airport by IHG
See all 426 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 thrilled with how little a holiday to Enterprise costs! Expedia's packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Enterprise?
If you're looking to snag a cheap Enterprise holiday package, consider visiting in April, September and October. You'll typically find better rates on accommodation and flights during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Enterprise?
The ideal length of your Enterprise holiday depends on what you'd like to see. Usually, a handful of days to a week will give you time to visit all the major attractions and explore some hidden gems along the way.
How to find the best Enterprise package deals?
Start your search for an Enterprise package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Enterprise package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Enterprise adventure off to a flying start.
Is it cheaper to book an Enterprise holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking hotels and flights individually. 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 great deals to see how much you can save.
When to book a holiday package to Enterprise?
Secure amazing discounts by booking your flights in advance with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Enterprise break.
How to plan a trip to Enterprise?

  1. Pick the perfect time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to go to Enterprise.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and dining out to activities and airfares. Your accommodation will likely be the largest expense during your trip to Enterprise.
  3. Decide your trip length: Think about how long you'd like to spend exploring Enterprise. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Combine your airfare and accommodation: After you've settled on your travel dates and duration, lock in the right 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. 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.