Success Holidays from £485

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to £335 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Packages with flights are ATOL protected
Price found within the past 48 hours. Click for updated prices.
The Chancellor Hotel

The Chancellor Hotel

3 out of 5
per person
17 Oct - 19 Oct
found 11 hours ago
Return flight included
Kingston (KIN) to Port of Spain (POS)
7/10 Good! (30 reviews)
Overall. It was quiet and cozy.

Reviewed on 13 Jul 2025

Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
Downtown Port of Spain
per person
17 Oct - 19 Oct
found 11 hours ago
Return flight included
Kingston (KIN) to Port of Spain (POS)
9.2/10 Wonderful! (1,008 reviews)
The Hyatt Trinidad is our home away from home. We love it there. Angelique is the day shift supervisor. She is awesome. She’s always doing nice things for us to make our stay comfortable. Z works in the kitchen and she always goes out of her way to greet us and do little extra things for us during breakfast. She’s the best. Housekeeping was on point as usual. The breakfast buffet is the best in Trinidad Tobago hands down. Perfect mix of island and American food. The front desk staff very friendly and know us by name. We love that. Definitely the best hotel in Trinidad/Tobago for value and price.

Reviewed on 9 Aug 2025

Cara Hotels Trinidad

Cara Hotels Trinidad

3 out of 5
per person
17 Oct - 19 Oct
found 11 hours ago
Return flight included
Kingston (KIN) 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

Hilton Trinidad & Conference Centre

Hilton Trinidad & Conference Centre

4.5 out of 5
per person
17 Oct - 19 Oct
found 11 hours ago
Return flight included
Kingston (KIN) to Port of Spain (POS)
8/10 Very Good! (1,006 reviews)
The locals call it the upside down hotel. It is fascinating that you have to take the elevator down for the rooms. Gorgeous views of the city

Reviewed on 9 Aug 2025

Chaquacabana Resort & Beach Club

Chaquacabana Resort & Beach Club

3 out of 5
per person
17 Oct - 19 Oct
found 11 hours ago
Return flight included
Kingston (KIN) to Port of Spain (POS)
6/10 (75 reviews)
Fun for families with kids. Beautiful setting and scenery but hotel needs a lot of upkeep .the room was great and big and comfy. Water pressure was really weird,.too strong and shooting out the shower head and faucet. Bed and pillows were extremely comfortable! Water bottles and toiletries were a nice extra in the room. Breakfast was included for our family, it was good and big portions. I would go back. The only negative was there was a party in a bungalow next to us but the AC fan was loud enough for me not to hear their music.

Reviewed on 2 Aug 2025

Where to stay in Success

Find the best Success areas and neighborhoods for the activities you enjoy most. Learn more about Success
Default Image

Downtown Port of Spain

2 out of top 10 points of interest in this area

If you're spending some time in Downtown Port of Spain, Queen's Park Savanah and National Museum and Art Gallery are top sights worth seeing.

Find hotels in Downtown Port of Spain

Top hotels in Success

BEAUTIFUL HOME IN PORT OF SPAIN TRINIDAD

BEAUTIFUL HOME IN PORT OF SPAIN TRINIDAD

Laventille, Port Of Spain Trinidad, San Juan-Laventille
Amazing hostess and beautiful home!
"Glendon has a beautiful home that is surrounded by a secured gate and protected with an alarm system. Her home easily accommodated my 20 family members and friends, who came on our trip, and could’ve easily accommodated to additional guest for a total of 22. Her cooking is amazing, there is a neat ..."

Reviewed on 30 Jun 2024

Get rates
BEAUTIFUL HOME IN PORT OF SPAIN TRINIDAD
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 £216 per night from 23 Aug to 24 Aug
£216
23 Aug - 24 Aug
includes taxes & fees
9/10 Wonderful! (1,007 reviews)
"Very nice hotel"

Reviewed on 7 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 17 Aug to 18 Aug
£160
17 Aug - 18 Aug
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"The scenery and ambience was everything. The pool area is just what I needed to complete the trip. The place is clean and breath taking will definitely book again. 5 stars and the mangers and ppl who work there are awesome and very friendly sometimes even go out there way to make sure you are good. ..."

Reviewed on 9 Aug 2025

Hilton Trinidad & Conference Centre
See all 384 properties in Success
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 a Success travel package cost?
Explore the best of Success from as low as £485. Choose from a great selection of flights, hotels and rental cars to suit every budget. Land even better deals when you add a few experiences or tours to your travel package.
If I'm not able to travel, can I cancel my Success travel package?
Yes, it's possible to cancel your Success booking if your plans have changed. Whether you'll incur a penalty or not depends on your airline, hotel or car rental company. You may be able to cancel or change free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.
How do I get a cheap travel package to Success?
Lock in flights that suit your schedule, add a hotel room to your booking and watch the savings grow with a Success travel package. It's that simple! From flights and hotels to rental cars and activities, Expedia is where your cheap holiday begins. And with more than 550 partner airlines and 1,000,000 hotel options around the globe to choose from, you won't be short of choice.
Does Expedia offer Book Now, Pay Later Success holidays?
Your bank balance shouldn't stop you from taking a holiday, so Expedia has worked out a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a terrific getaway without exhausting your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your break. Consider one of these flexible payment options:

  • Pay monthly holidays: Klarna offers convenient monthly payment plans that work for all budget sizes, so you can jet away on that well-earned holiday now.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay for your holiday across multiple transactions.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to click that "book now" button, choose a low deposit holiday payment plan with Klarna.

What are the top hotels in Success?
Get your holiday off to a fantastic start by booking a room at Gascon Villas. It's one of most sought-after hotels in Success. Another cosy option is Hislop On The Hill.
How far in advance should I book my Success holiday?
It can be tricky to know when is the perfect time to book your trip to Success. But typically the earlier you book, the better the prices. In some cases, you can reserve your flights and hotels up to a year before your departure date. If you're eager to escape on a last-minute getaway, no need to panic! There are incredible bargains featured on Expedia every day.
What does an Expedia Success travel package include?
Flights, hotels and rental cars — you'll discover them all here. With Expedia, you can shape your Success travel package the way you like it. All you have to do is work out just what you need. Once you've made your booking, you can add extras like activities and tours. The more you bundle, the more you save!
What should I know before booking a Success travel package?
So many places to explore, so many things to see. With a travel package, you'll be able to cross more of them off your list. Combine your flights, rental cars and hotels and score big savings.
Can I choose my airline with a Success Expedia travel package?
Yes, you sure can. Expedia has access to more than 550 airline partners across the globe, so opt for the carrier that's a good fit for your travel needs.

Popular places to visit

Royal Botanical Gardens

Royal Botanical Gardens

4/5(1 review)

Explore the great outdoors at Royal Botanical Gardens, a lovely green space in Port of Spain. Wander the area's waterfront or simply enjoy one of its top-notch restaurants.

Royal Botanical Gardens

Queen's Park Savanah

4/5(8 reviews)

Explore the great outdoors at Queen's Park Savanah, a lovely green space in Port of Spain. Wander the area's waterfront or simply enjoy one of its top-notch restaurants.

Queen's Park Savanah

Ariapita Avenue

3/5(1 review)

You can find the perfect gifts to bring home at Ariapita Avenue during your visit to Port of Spain. Discover the area's live music and shops.

Ariapita Avenue

Things to do

Street Food and a Taste of Trinidad Night life

Street Food and a Taste of Trinidad Night life

£60
per adult
Street Food and a Taste of Trinidad Night life
Caroni Wetlands Sunset Boat Tour

Caroni Wetlands Sunset Boat Tour

£52
per adult
94% of travellers recommend
Caroni Wetlands Sunset Boat Tour
beachgoers enjoying the sun in Trinidad and Tobago

Day Trip to Las Cuevas Beach

£53
per adult
100% of travellers recommend
Day Trip to Las Cuevas Beach
See all activities in Port of Spain

* 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.