Enterprise Vacations from $675

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The Latest Enterprise vacation packages

Price found within the past 48 hours. Click for updated prices.
Woodbrook on the Avenue

Woodbrook on the Avenue

2.5 out of 5
Woodbrook
Price was $876, price is now $675 per person
$675
per person
Sep 22 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
9/10 Wonderful! (85 reviews)
Room was super clean and the staff was very courteous and helpful. The A/C worked just fine. I would stay here again

Reviewed on Jul 4, 2026

Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
Downtown Port of Spain
Price was $1,524, price is now $1,103 per person
$1,103
per person
Aug 27 - Sep 1
found 16 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
9.2/10 Wonderful! (1,047 reviews)
Breakfast was good daily,

Reviewed on Jul 8, 2026

Airport Suites Hotel

Airport Suites Hotel

3 out of 5
Price was $952, price is now $699 per person
$699
per person
Sep 22 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
6/10 (1,002 reviews)
Ease of check in.

Reviewed on Jul 8, 2026

The Chancellor Hotel

The Chancellor Hotel

3 out of 5
St. Anns
Price was $1,033, price is now $789 per person
$789
per person
Sep 22 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
7/10 Good! (37 reviews)
Shower was not properly functioning when asked to switch rooms front desk could not program room key - they gave me access to a second room so I can shower using the housekeeping key both rooms had 1 towel 1 face towel and no washcloths Bar onsite but no staff to serve drinks Ended up checking out early due to issues at property

Reviewed on Apr 8, 2026

Regent Star Hotel

Regent Star Hotel

3 out of 5
Price was $944, price is now $799 per person
$799
per person
Sep 22 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
6.8/10 (375 reviews)
This Hotel has bed bugs. I stayed here for one night because i had a flight going out the next day. When i woke up to get ready for my flight i was bitten up very badly and it wasn’t mosquitos . This hotel is TERRIBLE

Reviewed on Jul 4, 2026

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What to do in Enterprise

Food Experience at Night

Food Experience at Night

$90
per adult
100% of travellers recommend
Food Experience at Night
monument in the middle of a park in Trinidad and Tobago

Half-Day Port of Spain Highlights & Maracas Bay Tour

$80
per adult
96% of travellers recommend
Half-Day Port of Spain Highlights & Maracas Bay Tour
The Scarlet Ibis - Caroni Swamp Tour

The Scarlet Ibis - Caroni Swamp Tour

$75
per adult
The Scarlet Ibis - Caroni Swamp Tour
See all activities in Enterprise

Enterprise Hotel Deals

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
$249 nightly
The price is $276 total per night from Aug 7 to Aug 8
$276 total
Aug 7 - Aug 8
Total with taxes and fees
9.2/10 Wonderful! (1,053 reviews)
"Breakfast was good daily,"

Reviewed on Jul 8, 2026

Hyatt Regency Trinidad
Kapok Hotel

Kapok Hotel

4 out of 5
16-18 Cotton Hill St Clair Port of Spain Trinidad
$152 nightly
The price is $167 total per night from Jul 10 to Jul 11
$167 total
Jul 10 - Jul 11
Total with taxes and fees
8.6/10 Excellent! (1,005 reviews)
"Staff was so friendly and the location was nice for some long walks"

Reviewed on Jul 6, 2026

Kapok Hotel
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
$214 nightly
The price is $233 total per night from Jul 12 to Jul 13
$233 total
Jul 12 - Jul 13
Total with taxes and fees
8.4/10 Very Good! (1,008 reviews)
"We had the most incredible stay here!! The staff are SO friendly and the property is gorgeous! We had a wonderful time in Trinidad staying at the most beautiful Hilton I have ever been to. I will absolutely be staying here again!"

Reviewed on Jul 8, 2026

Hilton Trinidad & Conference Centre
See all 470 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.

Find the Best Enterprise Vacation Packages

Enterprise Essential Information

Language
English
Currency
Trinidad and Tobago dollars
Closest Airport
Piarco Intl. Airport (POS)

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Frequently asked questions

How much does an Enterprise vacation package cost?
Offering excellent value package deals from $675 on Expedia, you'll be thrilled with how little a vacation to Enterprise costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Enterprise?
If you're looking to book a cheap Enterprise vacation package, consider visiting in November, December and January. You'll usually find lower prices on flights and accommodations during these months — perfect for a budget-friendly getaway.
How many days is enough for Enterprise?
Generally, a handful of days is enough to tick off the top attractions during your Enterprise vacation. However, if you'd like to have more time to unwind or go on day trips, consider extending your trip.
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 vacation as a package?
An Expedia vacation 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 vacation 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.
Does Expedia offer Book Now, Pay Later Enterprise vacation packages?
Set off on your dream trip to Enterprise with our Book Now, Pay Later vacations. No need to save like crazy or hold off until your next payday — we've joined forces with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no hidden or late payment fees, it's easy to budget for your trip and snap up travel deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.