Success 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
Price found within the past 48 hours. Click for updated prices.
- Airport Suites Hotel
Jul 10 - Jul 13Airport Suites Hotel + Flight
Piarco3 nights6.0/10 - (1,009 reviews)"Staff was absolutely amazing and helpful, I found that the property was okay. Noting spectacular nothing really around. Get food from the airport first before leaving. Rooms were basic but big .. literally a place to stay even tho I wasn’t really feeling the bed and atmosphere it did the job."Reviewed June 9, 2026Roundtrip • Hamilton (YHM) - Trinidad (POS)YHM - POS • 1 stop POS - YHM • 1 stopCA $940CA $759found 14 hours agoper traveller - Willard's Bed and Breakfast
Jul 29 - Jul 30Willard's Bed and Breakfast + Flight
Tunapuna1 night9.6/10 - Exceptional (78 reviews)"Wonderful! We couldn’t have wished for such a warm and restful stay! A beautiful house, managed by an amazing family! The views of the hills in the distance and the staghorn plants that surround as you take a dip in the pool are incredibly peaceful. The breakfast was amazing, the neighbors and the shop up the road were so kind. We walked to grocrey stores and restaurants every evening! We will be back every time we visit Trinidad. "Reviewed February 12, 2026Roundtrip • Montreal (YUL) - Trinidad (POS)YUL - POS • 2 stops POS - YUL • 2 stopsCA $2,358CA $1,233found 21 hours agoper traveller - The Cosy Konak
Jul 29 - Jul 30The Cosy Konak + Flight
Woodbrook1 night10/10 - Exceptional (1 review)"Its open space and family friendly"Reviewed May 5, 2026Roundtrip • Montreal (YUL) - Trinidad (POS)YUL - POS • 2 stops POS - YUL • 2 stopsCA $2,409CA $1,279found 21 hours agoper traveller - Woodbrook on the Avenue
Aug 23 - Aug 30Woodbrook on the Avenue + Flight
Woodbrook7 nights9.0/10 - Wonderful (84 reviews)"The accommodation was ideal for a couple nights, close to The Avenue which had everything from bars, food courts and supermarkets. Air-conditioning,Tv"Reviewed June 2, 2026Roundtrip • Toronto (YYZ) - Trinidad (POS)YYZ - POS • Nonstop POS - YYZ • NonstopCA $1,373CA $1,019found 1 day agoper traveller - The Chancellor Hotel
Aug 23 - Aug 30The Chancellor Hotel + Flight
St. Anns7 nights7.0/10 - Good (37 reviews)"Staff was very friendly. The hotel is gated and always had someone available to open/close it. Check in and check out was a breeze. The hotel is within walking distance of a coffee shop, some local restaurants, the Savannah, gardens, zoo. There was no continental breakfast, no bar even though one was there. We didn't use the pool. Property could use some upgrades and renovation."Reviewed April 8, 2026Roundtrip • Toronto (YYZ) - Trinidad (POS)YYZ - POS • Nonstop POS - YYZ • NonstopCA $1,678CA $1,265found 1 day agoper traveller
Where to stay in Success
Find the best Success areas and neighborhoods for the activities you enjoy most. Learn more about Success
Downtown Port of Spain
3 out of top 10 points of interest in this area
4/5(2 area reviews)
While visiting Downtown Port of Spain, you might make a stop by sights like Queen's Park Savanah and Queen's Park Savannah Grand Stand.
Success Hotel Deals
BEAUTIFUL HOME IN PORT OF SPAIN TRINIDAD
Laventille, Port Of Spain Trinidad San Juan-Laventille
10/10 Exceptional! (2 reviews)
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 Jun 30, 2024
Hyatt Regency Trinidad
No 1 Wrighton Road Port of Spain Trinidad
Fully refundableReserve now, pay when you stay
The price is CA $300 per night from Jul 9 to Jul 10
CA $300
CA $365 total
Jul 9 - Jul 10
includes taxes & fees
9.2/10 Wonderful! (1,040 reviews)
"I love the outdoor dining and staff very friendly and very helpful."
Reviewed on Jun 6, 2026
Kapok Hotel
16-18 Cotton Hill St Clair Port of Spain Trinidad
The price is CA $184 per night from Jun 15 to Jun 16
CA $184
CA $227 total
Jun 15 - Jun 16
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"Very pleasant six nights stay breakfast was good. Staff was friendly overall I’ll give excellent review housekeeping was very helpful"
Reviewed on Jun 6, 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.
Frequently asked questions
Discover the most popular places to visit in Success
Queen's Park Savanah
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 Oval
Catch an event at Queen's Park Oval during your trip to Port of Spain. Stroll along the area's waterfront, or simply savor its top-notch restaurants.
Shops of Maraval
You can enjoy retail therapy at Shops of Maraval during your visit to Port of Spain.
Things to do
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.