Diego Martin Vacations from $553

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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.
Woodbrook on the Avenue

Woodbrook on the Avenue

2.5 out of 5
Woodbrook
Price was $781, price is now $553 per person
$553
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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
Save 100% on your flight
Price was $1,494, price is now $937 per person
$937
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Port of Spain (POS)
9.2/10 Wonderful! (1,004 reviews)
The rooms had no toothpaste and the hotel had a old smell otherwise it was a beautiful hotel

Reviewed on Sep 18, 2025

Hilton Trinidad & Conference Centre

Hilton Trinidad & Conference Centre

4.5 out of 5
Price was $1,107, price is now $865 per person
$865
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Port of Spain (POS)
8/10 Very Good! (1,008 reviews)
I have stayed at this property a few times. But this last time is showing a decline in service. The front desk girls were not welcoming. They were not trying to be helpful. Borderline rude. I had a situation with my daughter and we needed a room upgrade. I had to really assert myself and after several hours I finally got someone in the back office to help. I was willing to pay. I am a hiltons honors member as well and that was totally overlooked. The property is truly beautiful and I have always enjoyed my stays here. I would hate to see this Hilton go down because of the staff’s inability to realize how much their attitudes can make a difference.

Reviewed on Sep 9, 2025

Chaquacabana Resort & Beach Club

Chaquacabana Resort & Beach Club

3 out of 5
Price was $1,055, price is now $831 per person
$831
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Port of Spain (POS)
6/10 (81 reviews)
I was amazed at how beautifully designed this hotel was the rooms were gorgeous. Near the rooms are armed beautiful dark skinned men standing in front of a booth all night lol really makes you feel protected😜 the food and drinks were great as well as the views from the private beach

Reviewed on Sep 11, 2025

West Palm Hotel

West Palm Hotel

3 out of 5
Price was $794, price is now $633 per person
$633
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Port of Spain (POS)
6.2/10 (94 reviews)
Very affordable rates for people looking for somewhere to rest their head for vacation. Not much else to offer as a hotel.

Reviewed on Aug 21, 2025

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Diego Martin Hotel Deals

The Royal Nest Trinidad

The Royal Nest Trinidad

3 out of 5
6 Sinclair Hill, Diego Martin, Diego Martin Regional Corporation
$175 nightly
The price is $191 total per night from Sep 20 to Sep 21
$191 total
Sep 20 - Sep 21
Total with taxes and fees
The Royal Nest Trinidad
Tony's Guest House

Tony's Guest House

2.5 out of 5
Papnis Dr, Cor Morne Coco, & Sierra Leone Rd, Diego Martin, Trinidad
Fully refundableReserve now, pay when you stay
$50 nightly
The price is $55 total per night from Oct 7 to Oct 8
$55 total
Oct 7 - Oct 8
Total with taxes and fees
7.8/10 Good! (25 reviews)
"it was a grate stay I enjoyed being in Trinidad at they guest house it close to a lot of places an the owner is just wonderful."

Reviewed on Jun 3, 2025

Tony's Guest House
Pool Jacuzzi Gulfview Townhome

Pool Jacuzzi Gulfview Townhome

2 out of 5
Diego Martin
$403 nightly
The price is $403 total per night from Oct 5 to Oct 6
$403 total
Oct 5 - Oct 6
Total with taxes and fees
Pool Jacuzzi Gulfview Townhome
See all 378 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.

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Frequently asked questions

How much does a Diego Martin vacation package cost?
Offering excellent value package deals from $553 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.