Enterprise Vacations from $502

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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 $804, price is now $502 per person
$502
per person
Jan 21 - Jan 28
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
18/10 Exceptional! (76 reviews)
Staff greeted me warmly and guided me to my room where I was able to store my luggage for a couple of hours. Room was clean, had wifi, air-conditioning, and hot water. I'm very happy with my stay.

Reviewed on Oct 28, 2025

Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
Downtown Port of Spain
Price was $909, price is now $656 per person
$656
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
18.4/10 Exceptional! (1,008 reviews)
Exceptional!! I had a great time!!!

Reviewed on Nov 19, 2025

Metro Hotel Couva

Metro Hotel Couva

3.5 out of 5
Price was $645, price is now $514 per person
$514
per person
Jan 21 - Jan 28
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
16.8/10 Exceptional! (416 reviews)
The place is decent and clean. Rooms are spacious

Reviewed on Nov 16, 2025

St Ann's Guest House Ltd.

St Ann's Guest House Ltd.

2.5 out of 5
Price was $753, price is now $607 per person
$607
per person
Jan 21 - Jan 28
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
12.4/10 Exceptional! (41 reviews)
Staff Deserves A Raised. VERY Professional, At There Job, Yes A Few Things Can Be Added To Uplift The Property! But Its A Good Spot & Near The Q.P.S Which Is Indeed Awesome!

Reviewed on May 27, 2025

The Chancellor Hotel

The Chancellor Hotel

3 out of 5
Price was $977, price is now $799 per person
$799
per person
Jan 21 - Jan 28
found 14 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
14.4/10 Exceptional! (31 reviews)
The staffs were very friendly. I Didn't use the pool. Supermarket was close by as well as a convenient store.

Reviewed on Nov 18, 2025

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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
$185 nightly
The price is $201 total per night from Dec 11 to Dec 12
$201 total
Dec 11 - Dec 12
Total with taxes and fees
9/10 Wonderful! (1,010 reviews)
rooms can use a little updating. colors are so bland.

Reviewed on Nov 18, 2025

Hyatt Regency Trinidad
The BRIX, Autograph Collection

The BRIX, Autograph Collection

4.5 out of 5
2-4 Coblentz Avenue Port of Spain Trinidad
Fully refundableReserve now, pay when you stay
$177 nightly
The price is $193 total per night from Dec 14 to Dec 15
$193 total
Dec 14 - Dec 15
Total with taxes and fees
9/10 Wonderful! (497 reviews)
had a wonderful stay. The staff were incredibly kind, helpful, and friendly throughout my visit. The room was very clean and comfortable. I would definitely stay here again!

Reviewed on Nov 17, 2025

The BRIX, Autograph Collection
Kapok Hotel

Kapok Hotel

4 out of 5
16-18 Cotton Hill St Clair Port of Spain Trinidad
$132 nightly
The price is $145 total per night from Dec 1 to Dec 2
$145 total
Dec 1 - Dec 2
Total with taxes and fees
8.2/10 Very Good! (999 reviews)
Everything was great

Reviewed on Nov 16, 2025

Kapok Hotel
See all 417 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 $502 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.