Diamond Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 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
Top hotels in Diamond
Tropikist Beach Hotel & Resort
77 Old Store Bay Rd Crown Point Tobago
S$191
10 Nov - 11 Nov
includes taxes & fees
8/10 Very good! (1,005 reviews)
"The rooms were very clean and welcoming. The staff was very nice and helpful."
Reviewed on 9 Oct, 2026
Coco Reef Resort and Spa
Coconut Bay Crown Point Tobago
S$435
11 Oct - 12 Oct
includes taxes & fees
7/10 Good! (551 reviews)
"Could not adjust ac, got sick because it was too cold Imconsistent service, inexperienced employees, dont seem.to want business No Nightly entertainment Would not waste my money here"
Reviewed on 10 Oct, 2026
Starfish Tobago Resort
Courland Bay Plymouth Tobago
Fully refundableReserve now, pay when you stay
S$256
10 Nov - 11 Nov
includes taxes & fees
6.8/10 (715 reviews)
"The property was in a decent area with beach access even though we didn’t go on the beach. The pool bar only had low-tier alcohol. There was no seating at the pool bar. There was no fan at the pool bar (badly needed). The servers at the morning breakfast weren’t friendly and looked like they didn’t ..."
Reviewed on 7 Oct, 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.
What to do in Diamond
Glass-Bottom Boat & snorkeling with Tobago Highlights Tour
S$149
per adult
74% of travellers recommend
Half Day Group Tour to Tobago Atlantic Coast
S$102
per adult
Frequently asked questions
How much does a Diamond holiday package cost?
You can snap up a holiday package to this top destination on Expedia. But how much your holiday to Diamond costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Diamond?
You can usually find lower prices and better availability in April, May and September. Take a look at our cheap Diamond holiday packages and you could score some great off-season deals.
How many days is enough for Diamond?
Generally, a handful of days is enough to explore the main attractions during your Diamond holiday. However, if you'd like to have some time to relax or go on day trips, think about extending your itinerary.
How to find the best Diamond package deals?
Use Expedia's handy filters to help you find some terrific Diamond package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Diamond package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your holiday package as early as possible.
Is it cheaper to book a Diamond holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging hotels and flights individually. Better still, you can tailor your Diamond trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a holiday package to Diamond?
If you've got your Diamond holiday dates locked in, book as early as you can to grab some terrific deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for travelling on a whim.
How to plan a trip to Diamond?
- Choose when to get away: Check your schedule and get your bags packed. Your favourite time of year and the type of activities available will also help you decide when to escape to Diamond.
- Figure out your budget: Make sure you have enough money to cover everything from dining out and transportation to experiences and flights. Your accommodation will probably be the biggest expense during your trip to Diamond.
- Set the duration of your trip: Start by making a list of all the attractions you want to get to in Diamond. Then, estimate how long you'll need at each, as well as any travel time.
- Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customised Diamond holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
