Success Vacation Packages

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Holiday Package Deals in Success

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 CA $1,111, price is now CA $780 per person
CA $780
per person
Nov 20 - Nov 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Port of Spain (POS)
8.8/10 Excellent! (74 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 Jul. 3, 2025

Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
Downtown Port of Spain
Price was CA $1,807, price is now CA $1,309 per person
CA $1,309
per person
Nov 20 - Nov 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Port of Spain (POS)
9.2/10 Wonderful! (1,004 reviews)
Rooms were spacious, comfortable and very clean. We LOVED looking out at the ocean from our picture window. The breakfast buffet was delightful. The staff was always available and quite helpful - they really made a difference.

Reviewed on Sep. 3, 2025

Cara Hotels Trinidad

Cara Hotels Trinidad

3 out of 5
Price was CA $1,606, price is now CA $1,228 per person
CA $1,228
per person
Nov 20 - Nov 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Port of Spain (POS)
7.6/10 Good! (219 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 Jul. 3, 2025

Radisson Hotel Trinidad

Radisson Hotel Trinidad

4 out of 5
Downtown Port of Spain
Price was CA $1,537, price is now CA $1,214 per person
CA $1,214
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Port of Spain (POS)
7/10 Good! (886 reviews)
Melissa very friendly. And the two budlers very friendly The female bar tenders is laking in customer service

Reviewed on Aug. 23, 2025

Mt. Plaisir Estate Hotel

Mt. Plaisir Estate Hotel

3 out of 5
Price was CA $4,694, price is now CA $3,727 per person
CA $3,727
per person
Nov 20 - Nov 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Port of Spain (POS)
10/10 Exceptional! (8 reviews)
Excellent hotel, clean rooms and friendly staff

Reviewed on Aug. 6, 2025

Where to stay in Success

Find the best Success areas and neighborhoods for the activities you enjoy most. Learn more about Success
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Downtown Port of Spain

2 out of top 10 points of interest in this area

While visiting Downtown Port of Spain, you might make a stop by sights like Queen's Park Savanah and National Museum and Art Gallery.

Find hotels in Downtown Port of Spain

Success 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 $268 per night from Sep 13 to Sep 14
CA $268
CA $326 total
Sep 13 - Sep 14
includes taxes & fees
Hyatt Regency Trinidad
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 CA $195 per night from Oct 7 to Oct 8
CA $195
CA $237 total
Oct 7 - Oct 8
includes taxes & fees
Holiday Inn Express Hotel & Suites Trincity Trinidad Airport by IHG
The BRIX, Autograph Collection

The BRIX, Autograph Collection

4.5 out of 5
2-4 Coblentz Avenue, Cascade, Port of Spain, Trinidad
Fully refundableReserve now, pay when you stay
The price is CA $242 per night from Sep 21 to Sep 22
CA $242
CA $290 total
Sep 21 - Sep 22
includes taxes & fees
The BRIX, Autograph Collection
See all 385 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Success vacation package cost?
Choose from any combination of car rentals, flights and hotels, and you can be vacationing in Success from just CA $780. And the more you bundle, the more cash you save. The vacation of your dreams has never been so affordable.
How do I get a cheap travel package to Success?
Combine your bookings with Expedia to save big bucks on your next big adventure. With over 550 partner airlines and 1,000,000 hotels worldwide, your Success vacation package can be customized exactly to suit your budget. With all that extra cash, why not add a few interesting activities and tours? It's an easy way to unlock even more bargains. Your dream getaway to Success is closer than you thought!
How far in advance should I book my Success vacation?
Smart travelers will likely want to book as early as possible. You can usually browse through international fares on Expedia up to 12 months before your flight. If you're purchasing tickets last minute, don't despair. Discounted prices occasionally become available in the last weeks before departure dates.
What does an Expedia Success travel package include?
Hotels, flights and a shiny set of wheels for your road trip adventures. Simply choose your favorite bundle and get access to incredible deals. Once you've made your booking, add on a couple of experiences and tours and watch your savings stack up. When it comes to crafting your Success break, you're the boss!
What should I know before booking a Success travel package?
You'll save big with an Expedia travel package. Combine your flights, rental cars and hotels and enjoy terrific discounts. Hotels aren't your only choice, however. We have oceanfront condos, cabins in the mountains and even ranches and treehouses!
If I'm not able to travel, can I cancel my Success vacation package?
We totally get it — the universe can throw the odd curveball. If you've booked a Success vacation package and need to cancel or amend it, we can help. We recommend checking out our Customer Service Portal first for information. But in general, if you've booked your package in the last 24 hours, you may be able to change your itinerary for free. If it's been more than 24 hours, your airline, hotel or car rental company may impose a fee.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.