Enterprise Vacations from $377

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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 $599, price is now $377 per person
$377
per person
Mar 18 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Port of Spain (POS)
9/10 Wonderful! (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

The Chancellor Hotel

The Chancellor Hotel

3 out of 5
Price was $726, price is now $514 per person
$514
per person
Mar 18 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Port of Spain (POS)
7.2/10 Good! (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

Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
Downtown Port of Spain
Price was $1,164, price is now $920 per person
$920
per person
Mar 9 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Port of Spain (POS)
9.2/10 Wonderful! (1,008 reviews)
The staff were efficient and friendly. The room is very nice and big and the sushi was great! Parking was a breeze

Reviewed on Jan 8, 2026

Chaquacabana Resort & Beach Club

Chaquacabana Resort & Beach Club

3 out of 5
Price was $867, price is now $705 per person
$705
per person
Mar 9 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Port of Spain (POS)
6/10 (87 reviews)
Property needs to have proper walkway to staircase to home.

Reviewed on Oct 13, 2025

Airport Inn

Airport Inn

3.5 out of 5
Price was $750, price is now $615 per person
$615
per person
Mar 9 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Port of Spain (POS)
8.2/10 Very Good! (115 reviews)
Cleanliness of the facility, proximity to the airport, helpfulness of host.

Reviewed on Dec 8, 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
$269 nightly
The price is $293 total per night from Feb 6 to Feb 7
$293 total
Feb 6 - Feb 7
Total with taxes and fees
9/10 Wonderful! (1,007 reviews)
Didn't have breakfast

Reviewed on Jan 11, 2026

Hyatt Regency Trinidad
Radisson Hotel Trinidad

Radisson Hotel Trinidad

4 out of 5
Wrightson Road Port of Spain Trinidad
Fully refundableReserve now, pay when you stay
$210 nightly
The price is $230 total per night from Jan 29 to Jan 30
$230 total
Jan 29 - Jan 30
Total with taxes and fees
7/10 Good! (941 reviews)
Clean room,excellent staff. Keep up the good work.

Reviewed on Jan 8, 2026

Radisson Hotel 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
$193 nightly
The price is $211 total per night from Jan 16 to Jan 17
$211 total
Jan 16 - Jan 17
Total with taxes and fees
8/10 Very Good! (1,000 reviews)
Yes

Reviewed on Jan 3, 2026

Hilton Trinidad & Conference Centre
See all 409 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 $377 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.