Princes Town Vacations from $444

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Your Princes Town Vacation

When you organize a vacation package to Princes Town, you can relax and enjoy your break knowing that all your travel plans are in order. Discover the charms of this vibrant city from your base in a neighborhood like Saint Andrew, which is good for walking. Gulf City Mall and Manny Ramjohn Stadium are just two of the main attractions to visit during a trip to Princes Town. Expedia will help you escape the everyday. Tailor your vacation to Princes Town to match your travel style, whatever that may be.

The Latest Princes Town vacation packages

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 $590, price is now $444 per person
$444
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Port of Spain (POS)
9/10 Wonderful! (76 reviews)
The room was clean and well prepared for us.

Reviewed on Feb 1, 2026

The Chancellor Hotel

The Chancellor Hotel

3 out of 5
Price was $717, price is now $553 per person
$553
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Port of Spain (POS)
7.2/10 Good! (31 reviews)
The staffs were very friendly. I Didn't use the pool. Supermarket was close by as well as a convenient store.

Reviewed on Nov 18, 2025

Chaquacabana Resort & Beach Club

Chaquacabana Resort & Beach Club

3 out of 5
Price was $734, price is now $597 per person
$597
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
6/10 (87 reviews)
Property needs to have proper walkway to staircase to home.

Reviewed on Oct 13, 2025

Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
Downtown Port of Spain
Price was $979, price is now $810 per person
$810
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Port of Spain (POS)
9.2/10 Wonderful! (1,008 reviews)
A++++++++. POOL BARTENDER ALWAYS A+++++ .PORTER TERRANCE ALWAYS A+++++++++++

Reviewed on Feb 15, 2026

Tstays Smart Hotel

Tstays Smart Hotel

2.5 out of 5
Woodbrook
Price was $613, price is now $516 per person
$516
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Port of Spain (POS)
No reviews
Room was clean an modern

Reviewed on Feb 6, 2026

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Princes Town Hotel Deals

Vintage Oaks Hideaway

Vintage Oaks Hideaway

2.5 out of 5
LP249 St Marys Village Princes Town
Get rates
Vintage Oaks Hideaway
Metro Hotel Couva

Metro Hotel Couva

3.5 out of 5
#1 Noel Street Couva
$60 nightly
The price is $66 total per night from Feb 19 to Feb 20
$66 total
Feb 19 - Feb 20
Total with taxes and fees
8.4/10 Very Good! (435 reviews)
Good

Reviewed on Jan 27, 2026

Metro Hotel Couva
Tradewinds Hotel

Tradewinds Hotel

3 out of 5
36-40 London Street San Fernando Trinidad
8.6/10 Excellent! (248 reviews)
Keisha on front desk was great. She saw I wasn’t good at going upstairs and switched me to ground floor without asking. Room was good with all facilities you could ask for. All the property was kept extremely clean. Breakfast at Trellis was excellent Loved the food & cocktails at the Bottle Staff ...

Reviewed on Feb 2, 2026

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Tradewinds Hotel
See all 86 properties in Princes Town
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.

Find the Best Princes Town Vacation Packages

Princes Town Essential Information

Language
English
Currency
Trinidad and Tobago dollars
Closest Airport
Piarco Intl. Airport (POS)
Population
10,000

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Frequently asked questions

How much does a Princes Town vacation package cost?
Offering great value package deals from $444 on Expedia, you'll be pleasantly surprised at how much a vacation to Princes Town costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Princes Town?
You're likely to find lower rates and better availability in November, December and January. Take a look at our cheap Princes Town vacation packages and you could score some great off-season deals.
How many days is enough for Princes Town?
The ideal length for your Princes Town vacation depends on what you'd like to see. Usually, a handful of days to a week will give you time to go to all the major sights and discover some hidden spots along the way.
How to find the best Princes Town package deals?
Landing a cheap Princes Town package deal is easy with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Princes Town package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Princes Town vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and accommodations individually. Better still, you can personalize your Princes Town getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Princes Town?
If you're planning an impromptu Princes Town adventure, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land sensational deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Princes Town vacation packages?
Secure your dream getaway to Princes Town with help from our Book Now, Pay Later vacations. There's no need to save like crazy or wait until the next payday — we've partnered with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily budget for your trip and snap up travel deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.