Diego Martin Vacations from $637

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Your Diego Martin Vacation

With all the details planned before you go away, our Diego Martin vacation packages mean you can focus more on having a great time. Whether you base yourself in the neighborhood of Saint James, which is great for nightlife, or somewhere else in town, this fun city offers an array of discoveries. Any trip to Diego Martin needs a well-designed itinerary. Fill yours with big-name attractions like Queens Park Savanah, Ariapita Avenue and Movietowne. Whoever you're taking a break with and whether your budget is big or small, your dream Diego Martin vacation is just clicks away with Expedia.

The Latest Diego Martin vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Trinidad & Conference Centre

Hilton Trinidad & Conference Centre

4.5 out of 5
Price was $822, price is now $637 per person
$637
per person
Jul 13 - Jul 16
found 16 hours ago
Roundtrip flight included
Georgetown (GEO) to Port of Spain (POS)
8.2/10 Very Good! (1,005 reviews)
My expectations given that Hilton Trinidad is an old hotel were simple. However, although The room was small it was well fitted. Mini fridge and microwave were appreciated. Pool area is huge. I felt like there is room for improvement, for example, a playground on the compound would be a welcomed addition. Breakfast was diverse, lots of fruit and veggies which we loved. The views of the city of Port of Spain always 10/10. The gym is fantastic. Hilton is like home, comfortable, relaxing and welcoming.

Reviewed on May 12, 2026

Woodbrook on the Avenue

Woodbrook on the Avenue

2.5 out of 5
Woodbrook
Price was $956, price is now $772 per person
$772
per person
Aug 5 - Aug 10
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Port of Spain (POS)
9/10 Wonderful! (82 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 $1,110, price is now $906 per person
$906
per person
Aug 5 - Aug 10
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Port of Spain (POS)
7/10 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 on Apr 8, 2026

Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
Downtown Port of Spain
Price was $1,446, price is now $1,184 per person
$1,184
per person
Aug 5 - Aug 10
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Port of Spain (POS)
9.2/10 Wonderful! (1,025 reviews)
Excellent staff , clean environment, delicious breakfast will definitely be back soon

Reviewed on May 12, 2026

Chaquacabana Resort & Beach Club

Chaquacabana Resort & Beach Club

3 out of 5
Price was $1,151, price is now $974 per person
$974
per person
Aug 5 - Aug 10
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Port of Spain (POS)
6/10 (103 reviews)
Te breakfast was oil,

Reviewed on Apr 1, 2026

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Diego Martin Hotel Deals

Mahogany Ridge Trinidad

Mahogany Ridge Trinidad

2 out of 5
LP 50 Fond Pois Doux Road Diego Martin Diego Martin Regional Corporation
$146 nightly
The price is $146 total per night from May 14 to May 15
$146 total
May 14 - May 15
Total with taxes and fees
Mahogany Ridge Trinidad
Gulfview Townhouse With Pool and Jacuzzi

Gulfview Townhouse With Pool and Jacuzzi

3.5 out of 5
Lot 13 Gulf View Drive Diego Martin Diego Martin
$468 nightly
The price is $468 total per night from May 14 to May 15
$468 total
May 14 - May 15
Total with taxes and fees
Gulfview Townhouse With Pool and Jacuzzi
This is a Family Friendly property ideal for groups of 6 people.

This is a Family Friendly property ideal for groups of 6 people.

Diego Martin Diego Martin Regional Corporation
$284 nightly
The price is $284 total per night from May 16 to May 17
$284 total
May 16 - May 17
Total with taxes and fees
8/10 Very Good! (2 reviews)
The host was very welcoming and accommodating. He was available to answer any questions and deal with any issues we had. The property and appliances needs updating. One bedroom had an oder for the whole length of our stay. We had to leave the door open so the smell wouldn't be so strong.One of the ...

Reviewed on Feb 21, 2026

This is a Family Friendly property ideal for groups of 6 people.
See all 396 properties in Diego Martin
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 Diego Martin Vacation Packages

Diego Martin Essential Information

Language
English
Currency
Trinidad and Tobago dollars
Closest Airport
Piarco Intl. Airport (POS)
Max Temp Winter
80ºF
Max Temp Summer
85ºF
Top Sights
Chaguaramas Military History & Aerospace Museum, Chaguaramas Boardwalk and Chaguaramas Golf Course

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Frequently asked questions

How much does a Diego Martin vacation package cost?
Offering excellent value package deals from $637 on Expedia, you'll be surprised at how little a vacation to Diego Martin costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Diego Martin?
You can generally find lower prices and greater availability in March, May and November. Take a look at our cheap Diego Martin vacation packages and you could land some great off-season discounts.
How many days is enough for Diego Martin?
Typically, a handful of days is enough to visit the main sights during your Diego Martin vacation. But if you'd like to have more time to rest or go on day tours, consider extending your itinerary.
How to find the best Diego Martin package deals?
Finding a cheap Diego Martin package deal is a breeze with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, add some filters and see what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Diego Martin 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 usually lower.
Is it cheaper to book a Diego Martin vacation as a package?
You can enjoy significant savings on your next Diego Martin retreat by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Diego Martin?
If you're considering an impromptu Diego Martin adventure, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Diego Martin?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Diego Martin.
  2. Work out your budget: Ensure you have enough money to pay for everything from food and transportation to experiences and flights. Your hotel will likely be the largest expense during your trip to Diego Martin.
  3. Use Expedia's trip planning tool to discover Diego Martin: Research every part of your trip to Diego Martin with this comprehensive planner. Invite your family and friends to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Work out your trip length: Consider how long you want to spend discovering Diego Martin. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
  5. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customized Diego Martin vacation package.
  6. Book any excursions or activities: Here's the fun part — locking in everything you want to do and see. Browse some of the exciting things to do in Diego Martin and reserve your tickets in advance to save time (and maybe some spending money too!).

Does Expedia offer Book Now, Pay Later Diego Martin vacation packages?
Jet off on your perfect escape to Diego Martin with help from Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait until your next payday — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans let you spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stick to your budget and snag great 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.