Enterprise Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Enterprise Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Airport Suites Hotel
CA $883
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Port of Spain (POS)
6/10 (1,005 reviews)
The staff was very helpful and accommodating. The room was very boutique like, however based on the price I would recommend additional items to be placed in the room e.g. drinking glass etc. however it was a very peaceful and quiet area and ideal for getaway and to rock back.
Reviewed on Aug 31, 2026
Crown Hotel Piarco
CA $1,054
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Port of Spain (POS)
7.6/10 Good! (30 reviews)
Hotel have a hyatt vibes very clean,air-conditioning works excellent only thing missing was breakfast but everything was excellent and checkout 24 hours a plus
Reviewed on Jul 30, 2026
Ready to book your vacation to Enterprise?
Enterprise Hotel Deals
Hyatt Regency Trinidad
No 1 Wrighton Road Port of Spain Trinidad
Fully refundableReserve now, pay when you stay
CA $330
CA $400 total
Sep 29 - Sep 30
includes taxes & fees
9.2/10 Wonderful! (1,077 reviews)
"Well kept property. Professional staff. The breakfast and dinner was spectacular. The Gym and pool was also great. I had an awesome stay at this hotel. We definitely be back."
Reviewed on Aug 31, 2026
Kapok Hotel
16-18 Cotton Hill St Clair Port of Spain Trinidad
CA $206
CA $255 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
"The rooms are always clean and the breakfast is good The furnishings are good. The television service does leave a little to be desired. It varies from room to room. It is nice to have a refrigerator in every room"
Reviewed on Aug 31, 2026
Airport Suites Hotel
7 Factory Road, Golden Grove Piarco Trinidad
CA $102
CA $126 total
Sep 8 - Sep 9
includes taxes & fees
6.2/10 (1,006 reviews)
"The staff was very helpful and accommodating. The room was very boutique like, however based on the price I would recommend additional items to be placed in the room e.g. drinking glass etc. however it was a very peaceful and quiet area and ideal for getaway and to rock back."
Reviewed on Aug 31, 2026
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.
What to do in Enterprise
Port of Spain & Fort George Sightseeing Tour
CA $76
per adult
100% of travellers recommend
Full-Day City Tour, Maracas Bay & Caroni Bird Sanctuary
CA $159
per adult
100% of travellers recommend
Frequently asked questions
How much does an Enterprise vacation package cost?
Offering excellent value package deals from CA $821 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?
- 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.
- 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.
- 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.
- 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
