Trenchtown Holidays from AU$1,055

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Your Trenchtown Holiday

When it's time for your next adventure, choose a Trenchtown holiday package. From its culture to a whole lot more, there are loads of great reasons to pick this neighbourhood. Begin your trip to Trenchtown by visiting nearby attractions such as National Gallery of Jamaica, Bob Marley Museum and Jamaica House. Whatever your travel plans or budget, booking the ultimate Trenchtown holiday is simple with Expedia.

Top Holiday Package Deals in Trenchtown

Price found within the past 48 hours. Click for updated prices.
New Kingston C A Guest Apartments I

New Kingston C A Guest Apartments I

3.5 out of 5
New Kingston
Price was AU$1,488, price is now AU$1,055 per person
AU$1,055
per person
15 May - 18 May
found 1 day ago
Return direct flight included
Calgary (YYC) to Kingston (KIN)
7.4/10 Good! (8 reviews)
I booked as a part of a group of 4 for carnival and have a great stay. Highly recommended. Big up to Kevin and Mark

Reviewed on 2 May 2018

The Country Club Villa II

The Country Club Villa II

3.5 out of 5
Price was AU$1,556, price is now AU$1,092 per person
AU$1,092
per person
15 May - 18 May
found 1 day ago
Return direct flight included
Calgary (YYC) to Kingston (KIN)
9.4/10 Exceptional! (11 reviews)
New Kingston Apt at Kensington Court

New Kingston Apt at Kensington Court

3.5 out of 5
New Kingston
Price was AU$1,660, price is now AU$1,171 per person
AU$1,171
per person
15 May - 18 May
found 1 day ago
Return direct flight included
Calgary (YYC) to Kingston (KIN)
No reviews
The Bailey's New Kingston Suites

The Bailey's New Kingston Suites

3.5 out of 5
New Kingston
Price was AU$1,556, price is now AU$1,124 per person
AU$1,124
per person
15 May - 18 May
found 1 day ago
Return direct flight included
Calgary (YYC) to Kingston (KIN)
No reviews
20 South Kingston Luxury Apartment

20 South Kingston Luxury Apartment

3 out of 5
Half Way Tree
Price was AU$1,616, price is now AU$1,211 per person
AU$1,211
per person
15 May - 18 May
found 1 day ago
Return direct flight included
Calgary (YYC) to Kingston (KIN)
9.2/10 Wonderful! (10 reviews)
Quiet, clean. Wifi, comfortable with lots of space...

Reviewed on 17 Mar 2021

Our guide on where to stay in Trenchtown

Find the best Trenchtown areas and neighborhoods for the activities you enjoy most. Learn more about Trenchtown
Devon House featuring a house and a garden

New Kingston

3 out of top 10 points of interest in this area

New Kingston is known for its ample dining options, and you can make a stop by Devon House and Kingston and St. Andrew Parish Library while in the area.

Find hotels in New Kingston

Our pick of the best Trenchtown Hotel Deals

ROK Hotel Kingston, Tapestry Collection by Hilton

ROK Hotel Kingston, Tapestry Collection by Hilton

4 out of 5
2-4 King Street Kingston
Fully refundableReserve now, pay when you stay
The price is AU$288 per night from 29 Mar to 30 Mar
AU$288
29 Mar - 30 Mar
includes taxes & fees
8.8/10 Excellent! (1,178 reviews)
It’s a good overnight stay, the staff is wonderful and the property is comfortable.

Reviewed on 2 Mar 2026

ROK Hotel Kingston, Tapestry Collection by Hilton
S Hotel Kingston

S Hotel Kingston

4.5 out of 5
1 St Lucia Avenue Kingston Saint Andrew
Fully refundableReserve now, pay when you stay
The price is AU$321 per night from 14 Mar to 15 Mar
AU$321
14 Mar - 15 Mar
includes taxes & fees
9.4/10 Exceptional! (1,635 reviews)
The S hotel is hands down the best in Kingston for business and personal travel. Very clean,pleasant staff, great parking and very central

Reviewed on 2 Mar 2026

S Hotel Kingston
R Hotel Kingston

R Hotel Kingston

4 out of 5
2 Renfrew Road , Kingston 10, Jamaica Kingston Jamaica
Fully refundableReserve now, pay when you stay
8.4/10 Very Good! (1,171 reviews)
Stayed here in various rooms all great

Reviewed on 1 Mar 2026

Get rates
R Hotel Kingston
See all 1,569 properties in Trenchtown
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 Trenchtown holiday package cost?
Be ready to book, because a trip to Trenchtown starts from only AU$1,055. When you bundle your flights, hotels and car rentals into a holiday package, you'll enjoy the best deals.
How do I get a cheap travel package to Trenchtown?
Our Trenchtown holiday packages promise plenty of savings for the savvy explorer. For the best deal, simply combine your hotel, flights and extras (such as activities) into one neat package. But bargain prices are just the beginning of your next awesome adventure. Book with Expedia and you'll have more than 550 air carriers and 1 000 000 hotels around the globe to pick from. Whatever your style or budget, there's a holiday package here just for you.
Where should I stay in Trenchtown?
Stay where the action happens. Many people favor hotels within easy reach of top attractions, like National Gallery of Jamaica, Bob Marley Museum and Devon House.
How far in advance should I book my Trenchtown holiday?
Travellers are usually able to compare international flights on Expedia within 12 months of the departure date. Booking late? With a little bit of luck, it's still possible to score a cheap ticket just weeks before your journey.
What does an Expedia Trenchtown travel package include?
Rental cars, hotels and flights — we've got them covered. With Expedia, you can shape your Trenchtown package the way you want. All you have to do is figure out just what you need. Once you've made your booking, you can add on extras like tours and activities. The more you bundle, the more you save!
What should I know before booking a Trenchtown travel package?
Bundling your bookings into a Trenchtown holiday package is the most convenient way to organise your trip. Not only that, you'll save when you combine your hotels, flights and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with a Trenchtown Expedia holiday package?
Yes — that's one of the best things about an Expedia holiday package. You get to choose. We have access to more than 550 partner airlines around the world, so you have lots of choice when creating your Trenchtown adventure.
If I'm not able to travel, can I cancel my Trenchtown holiday package?
Yes, you can. We totally understand that even the best-laid plans can fail, so we're happy to help if you need to make changes to your Trenchtown holiday package. You may be able to change or cancel your itinerary for free if you've booked within 24 hours. Your hotel, airline or car rental company may impose a fee if your booking was made more than 24 hours ago. Take a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the nitty-gritty on change fees.

Activities

Kingston Dub Club Sundays

Kingston Dub Club Sundays

AU$94
per adult
Kingston Dub Club Sundays
displays at the bob marley museum in Jamaica

Kingston Tour & Bob Marley Museum Admission

AU$117
per adult
74% of travellers recommend
Kingston Tour & Bob Marley Museum Admission
Kingston City Food Tour

Kingston City Food Tour

AU$260
per adult
100% of travellers recommend
Kingston City Food Tour
See all activities in Kingston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.