Enterprise Vacation Packages

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Top Enterprise Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Metro Hotel Couva

Metro Hotel Couva

3.5 out of 5
Price was CA $751, price is now CA $666 per person
CA $666
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Port of Spain (POS)
8.4/10 Very good! (468 reviews)
the rooms were smelly

Reviewed on Jul 8, 2026

Airport Suites Hotel

Airport Suites Hotel

3 out of 5
Price was CA $968, price is now CA $731 per person
CA $731
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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 CA $1,028, price is now CA $834 per person
CA $834
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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

Woodbrook on the Avenue

Woodbrook on the Avenue

2.5 out of 5
Woodbrook
Price was CA $884, price is now CA $730 per person
CA $730
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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 CA $1,484, price is now CA $1,289 per person
CA $1,289
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Port of Spain (POS)
9.2/10 Wonderful! (1,047 reviews)
Breakfast was good daily,

Reviewed on Jul 8, 2026

Ready to book your vacation to Enterprise?

 

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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
The price is CA $322 per night from Aug 8 to Aug 9
CA $322
CA $391 total
Aug 8 - Aug 9
includes taxes & 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
The price is CA $189 per night from Jul 12 to Jul 13
CA $189
CA $235 total
Jul 12 - Jul 13
includes taxes & 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
The price is CA $272 per night from Jul 17 to Jul 18
CA $272
CA $330 total
Jul 17 - Jul 18
includes taxes & 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Enterprise

monument in front of a glass building in Trinidad and Tobago

Port of Spain & Fort George Sightseeing Tour

CA $78
per adult
100% of travellers recommend
Port of Spain & Fort George Sightseeing Tour
Statue in city of Trinidad

Full-Day City Tour, Maracas Bay & Caroni Bird Sanctuary

CA $163
per adult
100% of travellers recommend
Full-Day City Tour, Maracas Bay & Caroni Bird Sanctuary
Food Experience at Night

Food Experience at Night

CA $128
per adult
100% of travellers recommend
Food Experience at Night
See all activities in Enterprise

Frequently asked questions

How much does an Enterprise vacation package cost?
Offering excellent value package deals from CA $666 on Expedia, you'll be pleasantly surprised at how much 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'd like to snag a cheap Enterprise vacation package, consider visiting in April, September and October. You're likely to find lower prices on flights and accommodations during these quieter months — ideal for a budget-friendly break.
How many days is enough for Enterprise?
The ideal length of your Enterprise vacation depends on what you'd like to do. Generally, a few days to a week will give you plenty of time to check out all the main sights and explore some hidden gems along the way.
How to find the best Enterprise package deals?
Bagging a cheap Enterprise package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, add some filters and browse what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Enterprise package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book an Enterprise vacation as a package?
You can enjoy significant savings on your Enterprise getaway by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to see the best flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Enterprise?
Land fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Enterprise getaway.
How to plan a trip to Enterprise?

  1. Choose when to get away: Check your calendar and pack your bags. Your favourite season and the available activities will also help you decide when to escape to Enterprise.
  2. Plan your budget wisely: As well as the price of your stay, you should consider other expenses. These include food, flights and transportation. Also, set aside some extra funds for unexpected costs that may crop up during your trip to Enterprise.
  3. Determine how many days away: Start by compiling a list of the sights and activities you want to experience in Enterprise. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalized Enterprise vacation package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.