Enterprise Vacations from $566

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The Latest Enterprise vacation packages

Price found within the past 48 hours. Click for updated prices.
Vintage Oaks Hideaway

Vintage Oaks Hideaway

2.5 out of 5
Price was $662, price is now $566 per person
$566
per person
Jul 23 - Jul 26
found 24 hours ago
Roundtrip flight included
Georgetown (GEO) to Port of Spain (POS)
No reviews
Cascadia Hotel

Cascadia Hotel

3 out of 5
Price was $840, price is now $722 per person
$722
per person
Aug 1 - Aug 7
just found
Roundtrip flight included
New York (JFK) to Port of Spain (POS)
5.4/10 (69 reviews)
The breakfast was wonderful

Reviewed on Apr 26, 2026

West Palm Hotel

West Palm Hotel

3 out of 5
Price was $708, price is now $610 per person
$610
per person
Jul 23 - Jul 26
found 24 hours ago
Roundtrip flight included
Georgetown (GEO) to Port of Spain (POS)
6/10 (120 reviews)
The receptionist was so welcoming and assisted us with breakfast when we couldn’t be there on time. Big up the chef for his delicious food, my child loves his fish in coconut milk and eggs 👍. Our room was generally clean and the environment as well together with, the fridge, microwave and Cable TV was in proper working condition. I would definitely recommend staying a night or two.

Reviewed on Mar 23, 2026

The Bey

The Bey

3 out of 5
Price was $1,149, price is now $1,006 per person
$1,006
per person
Jul 24 - Jul 29
found 18 hours ago
Roundtrip flight included
New York (JFK) to Port of Spain (POS)
10/10 Exceptional! (1 review)
Cattleya Hotel

Cattleya Hotel

3 out of 5
Price was $643, price is now $595 per person
$595
per person
Jul 30 - Aug 3
just found
Roundtrip flight included
New York (NYC) to Port of Spain (POS)
6.2/10 (65 reviews)
The hotel was ok , I think breakfast should start around 6am in the morning to accommodate travelers leaving to go on the road or to travel back home or to another country but other wise it was ok .

Reviewed on Apr 27, 2026

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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
$243 nightly
The price is $265 total per night from Jun 5 to Jun 6
$265 total
Jun 5 - Jun 6
Total with taxes and fees
9.2/10 Wonderful! (1,033 reviews)
Great stay. Will be back.

Reviewed on May 14, 2026

Hyatt Regency Trinidad
Kapok Hotel

Kapok Hotel

4 out of 5
16-18 Cotton Hill St Clair Port of Spain Trinidad
$129 nightly
The price is $143 total per night from May 20 to May 21
$143 total
May 20 - May 21
Total with taxes and fees
8.4/10 Very Good! (1,008 reviews)
Cozy hotel in safe location close to downtown yet far enough away to avoid the hustle and bustle, and a short walk to the zoo, botanical garden, and Queen's Park. Friendly, professional, and helpful staff. Beautiful restaurant with superb menu, and its 8th-floor location has a wonderful panoramic ...

Reviewed on May 17, 2026

Kapok Hotel
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
$156 nightly
The price is $170 total per night from Jun 14 to Jun 15
$170 total
Jun 14 - Jun 15
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
Great location with kind and helpful staff

Reviewed on May 16, 2026

Holiday Inn Express Hotel & Suites Trincity Trinidad Airport by IHG
See all 435 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 $566 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.