Enterprise Holidays from £751

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    Packages with flights are ATOL protected

Top Enterprise Flight + Hotel Deals

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
per person
18 Sept - 24 Sept
just found
Return flight included
London (LON) to Port of Spain (POS)
9/10 Wonderful! (73 reviews)
The property is gated, clean and secure. The rooms are well appointed, and supported by polite and personal support staff. There is also 24/7 security surveillance.

Reviewed on 3 Jul 2025

Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
Downtown Port of Spain
per person
18 Sept - 24 Sept
just found
Return flight included
London (LON) to Port of Spain (POS)
9.2/10 Wonderful! (1,008 reviews)
Enjoyed my stay but customer service in the sense of attitudes and friendliness amongst some of the staff was lacking. My props in this area though definitely goes out to Shaquille at pool. Five gold stars for this gentleman. Another five gold stars also to Pamela (hope I remembered her name correctly), she had short hair and wore glasses. She worked at the pool with Shaquille. Food was delicious but a little pricey as expected at a hotel. Would stay here again.

Reviewed on 12 Aug 2025

Hilton Trinidad & Conference Centre

Hilton Trinidad & Conference Centre

4.5 out of 5
per person
18 Sept - 24 Sept
just found
Return flight included
London (LON) to Port of Spain (POS)
8/10 Very Good! (1,006 reviews)
The hotel is a typical Hilton property. Very clean. Staff is non-existent, slow and not very helpful or communicative. They ran out of washclothes and while we asked for 2 extra bath towels we nwver got them. We asked for 2 extra pillows and when they arrived the smelled so strongly of moth balls it made me sick.

Reviewed on 11 Aug 2025

Vintage Oaks Hideaway

Vintage Oaks Hideaway

2.5 out of 5
per person
18 Sept - 24 Sept
just found
Return flight included
London (LON) to Port of Spain (POS)
No reviews
Cara Hotels Trinidad

Cara Hotels Trinidad

3 out of 5
per person
18 Sept - 24 Sept
just found
Return flight included
London (LON) to Port of Spain (POS)
7.6/10 Good! (217 reviews)
The staff were sympathetic and friendly. The pool area and deck are nice. The view is gorgeous 😍😍. I would give an average rating as I believe the rooms can do with some upgrades. Otherwise can be an ideal stay for families who want to take a vacation away from home.😃

Reviewed on 3 Jul 2025

Enterprise Essential Information

Language
English
Currency
Trinidad and Tobago dollars
Closest Airport
Piarco Intl. Airport (POS)
Max Temp Winter
27ºC
Max Temp Summer
29ºC

Top hotels in Enterprise

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 £211 per night from 20 Aug to 21 Aug
£211
20 Aug - 21 Aug
includes taxes & fees
9/10 Wonderful! (1,012 reviews)
"Amazing staff, great views, excellent and prompt service ❤️"

Reviewed on 10 Aug 2025

Hyatt Regency 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
The price is £160 per night from 19 Aug to 20 Aug
£160
19 Aug - 20 Aug
includes taxes & fees
8/10 Very Good! (1,006 reviews)
"The hotel is a typical Hilton property. Very clean. Staff is non-existent, slow and not very helpful or communicative. They ran out of washclothes and while we asked for 2 extra bath towels we nwver got them. We asked for 2 extra pillows and when they arrived the smelled so strongly of moth balls ..."

Reviewed on 11 Aug 2025

Hilton Trinidad & Conference Centre
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
The price is £134 per night from 13 Sept to 14 Sept
£134
13 Sept - 14 Sept
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
"Great staff and great location"

Reviewed on 8 Aug 2025

Holiday Inn Express Hotel & Suites Trincity Trinidad Airport by IHG
See all 431 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does an Enterprise travel package cost?
Explore the best of Enterprise from as little as £751. We offer a great selection of rental cars, hotels and flights to suit every budget. Land even better deals when you add a couple of tours or activities to your package.
If I'm not able to travel, can I cancel my Enterprise travel package?
Don't worry if you're rethinking your Enterprise travel package — you can cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We realise life can sometimes throw a spanner in the works, so look up our Customer Service Portal if that occurs. When you're ready to make changes, we'll be here to help.
How do I get a cheap travel package to Enterprise?
One of the easiest ways to save money (and time) is to combine your bookings with Expedia. Flights, rental cars, hotels and activities — we've got everything you need. Pick the combination that best fits you and watch your savings stack up. We know a package deal is never one-size-fits-all. That's why Expedia offers over 550 air carriers and 1,000,000 hotels worldwide, which lets you customize your Enterprise getaway.
Does Expedia offer Book Now, Pay Later Enterprise holidays?
Expedia has teamed up with online lender Klarna to make booking your next break a little easier on the wallet. Paying by instalment means you can spread the costs of your dream holiday, leaving you with more money to play with while you're away. Klarna has several payment plans to pick from, so you're sure to find one that suits your budget. Consider these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month sounds right for you, Klarna offers just that! Paying in convenient monthly instalments will make your holiday dreams possible.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay off your holiday over multiple transactions.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan from Klarna.

What are the top hotels in Enterprise?
Whether you're planning to stay for just one night or a week in Enterprise, you'll get a solid night's sleep at Tcs Guesthouse. This option is popular with plenty of travellers.
How far in advance should I book my Enterprise holiday?
The earlier, the better. Airlines generally release flight tickets up to a year prior to departure, and this is your chance to land some rock-bottom prices. Boss just told you to use up all your holiday days in a few weeks? That's fine too — Expedia are never short of fantastic deals to send you off on the getaway of your dreams, at a price you can afford.
What does an Expedia Enterprise travel package include?
Expedia has all you need to organise your Enterprise getaway, but how your package is structured is entirely up to you. Select from a combination of flights, rental cars and hotels. Looking for some tours or experiences to fill in your time? Once you've made your booking, you can add them too. No matter your budget, there's a travel package to meet your needs.
What should I know before booking an Enterprise travel package?
So many places to venture to, so many things to see. With a travel package, you can cross more of them off your list. Combine your flights, hotels and rental cars and make big savings.
Can I choose my airline with an Enterprise Expedia travel package?
You can, and with over 550 airlines to pick from worldwide, you've got lots of choice. Look through the available options and find out which airline best fits your budget and needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.