Enterprise Vacations from $307

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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
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Port of Spain (POS)
8.8/10 Excellent! (70 reviews)
The property is gated, clean and secure. The rooms are well appointed, and supported by polite and personal support staff. There is also 24/7 security surveillance.

Reviewed on Jul 3, 2025

Hilton Trinidad & Conference Centre

Hilton Trinidad & Conference Centre

4.5 out of 5
Save 100% on your flight
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Port of Spain (POS)
8/10 Very Good! (1,003 reviews)
Hotel food is over priced.

Reviewed on Jul 18, 2025

Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
Downtown Port of Spain
Save 100% on your flight
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Port of Spain (POS)
9.2/10 Wonderful! (1,011 reviews)
The property is beautiful. The waiter at the waterfront restaurant was very pleasant and accommodating. However, upon check-in the lady could've been nicer. Also, the carpet in the room needs a deep cleaning. It was noticeably dirty.

Reviewed on Jul 19, 2025

Cara Hotels Trinidad

Cara Hotels Trinidad

3 out of 5
per person
Sep 11 - Sep 16
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
7.8/10 Good! (215 reviews)
The staff were sympathetic and friendly. The pool area and deck are nice. The view is gorgeous 😍😍. I would give an average rating as I believe the rooms can do with some upgrades. Otherwise can be an ideal stay for families who want to take a vacation away from home.😃

Reviewed on Jul 3, 2025

The Chancellor Hotel

The Chancellor Hotel

3 out of 5
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
7/10 Good! (29 reviews)
Overall. It was quiet and cozy.

Reviewed on Jul 13, 2025

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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
$197 nightly
The price is $215 total per night from Aug 6 to Aug 7
$215 total
Aug 6 - Aug 7
Total includes taxes and fees
9/10 Wonderful! (1,004 reviews)
Good luxury hotel.
"A little of luxury in Trinidad is what you’ll find here, I only had some snacks by the pool but unfortunately that was not up to par. Front desk staff were eager to help in anyway, they were very welcoming. Rooms were 5 star standard, which reflects the prices paid. I would recommend."

Reviewed on Jul 16, 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
$182 nightly
The price is $198 total per night from Aug 6 to Aug 7
$198 total
Aug 6 - Aug 7
Total includes taxes and fees
8/10 Very Good! (1,003 reviews)
"The staff was kind and accommodating."

Reviewed on Jul 18, 2025

Hilton Trinidad & Conference Centre
Radisson Hotel Trinidad

Radisson Hotel Trinidad

4 out of 5
Wrightson Road, Port of Spain, Trinidad
Fully refundable
$154 nightly
The price is $168 total per night from Jul 29 to Jul 30
$168 total
Jul 29 - Jul 30
Total includes taxes and fees
7/10 Good! (873 reviews)
"Ice machine is not working"

Reviewed on Jul 17, 2025

Radisson Hotel Trinidad
See all 425 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 $307 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.