Trenchtown Holidays from £690

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Your Trenchtown Holiday

From its highlights to its hidden treasures, this city is best experienced with a Trenchtown holiday package. Find somewhere to stay in Spanish Town Zone, which is good for views, history and walking. A trip to Trenchtown is a terrific opportunity to do a bit of sightseeing. Be sure to stop by renowned attractions like National Gallery of Jamaica, Bob Marley Museum and Devon House. Don't delay visiting this city any longer. Your ultimate Trenchtown holiday is just a few clicks away with Expedia.

New Kingston Guest Apartment at Westbury

New Kingston Guest Apartment at Westbury

3.5 out of 5
New Kingston
per person
12 Jul - 15 Jul
Return flight included
Port of Spain (POS) to Kingston (KIN)
8.6/10 Excellent! (28 reviews)
The property is well kept, the atmosphere relaxing, but most of all I felt very safe. The communication level however at first could've been better. The agent that I spoke with was very apologetic and very professional and courteous. Overall my stay was excellent. I'll recommend it to anyone seeking a quiet place away from home for a couple of days

Reviewed on 13 Nov 2022

Eclipse Suite Guest Apartments

Eclipse Suite Guest Apartments

3.5 out of 5
Havendale
per person
12 Jul - 15 Jul
Return flight included
Port of Spain (POS) to Kingston (KIN)
9/10 Wonderful! (21 reviews)
My biggest problem with the property was the water . And may i suggest that the owners consider putting in another ac unit in the living area or even ceiling fans. Other than these the unit in good location very private secure quite. Will stay again

Reviewed on 12 Jul 2019

The Cabin at Long Mountain Country Club

The Cabin at Long Mountain Country Club

3.5 out of 5
Beverly Hills
per person
12 Jul - 15 Jul
Return flight included
Port of Spain (POS) to Kingston (KIN)
8.8/10 Excellent! (11 reviews)
We spent over 3 weeks at the property and had no issues. It’s gated with security high up in the hills very safe and quiet. Friendly service and we would definitely recommend this property.

Reviewed on 8 Jan 2020

New Kingston Apartments at Kensington

New Kingston Apartments at Kensington

3.5 out of 5
New Kingston
per person
12 Jul - 15 Jul
Return flight included
Port of Spain (POS) to Kingston (KIN)
9.4/10 Exceptional! (11 reviews)
Central, very clean and just like the photos. We had a little issue with the guard not letting in a guest because he refused to turn down the loud music but other than that it was very good staying at the apartment cannot blame the guard either.

Reviewed on 27 Jan 2020

New Kingston Guest Apartments at Seymour

New Kingston Guest Apartments at Seymour

3.5 out of 5
New Kingston
per person
12 Jul - 15 Jul
Return flight included
Port of Spain (POS) to Kingston (KIN)
8.6/10 Excellent! (6 reviews)
Enjoyed my stay here at this apartment, it was perfect for my little trip. Sheldon is a great property manager. Thanks again for everything.

Reviewed on 11 Apr 2019

Prices and availability subject to change. Additional terms may apply.

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 park

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 Emancipation Park while in the area.

Find hotels in New Kingston

Top hotels in Trenchtown

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
The price is £159 per night from 4 May to 5 May
£159
per night
4 May - 5 May
8.6/10 Excellent! (1,003 reviews)
"Highly recommend if you're traveling to Kingston. Kind and professional staff. They are currently remodeling the pool so some amenities and services may be limited. Fortunately, the property is located near plenty of attractions and restaurants to compensate."

Reviewed on 20 Apr 2024

R Hotel Kingston
Spanish Court Hotel - A Small Luxury Hotel
Spanish Court Hotel - A Small Luxury Hotel
4.5 out of 5
1 St Lucia Avenue, Kingston, Saint Andrew
Fully refundableReserve now, pay when you stay
The price is £163 per night from 18 May to 19 May
£163
per night
18 May - 19 May
9.4/10 Exceptional! (1,067 reviews)
"Great Friendly Service. Excellent breakfast."

Reviewed on 22 Apr 2024

Spanish Court Hotel - A Small Luxury Hotel
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 £160 per night from 11 May to 12 May
£160
per night
11 May - 12 May
8.8/10 Excellent! (444 reviews)
"Loved the ambiance and decor of it all..."

Reviewed on 19 Apr 2024

ROK Hotel Kingston, Tapestry Collection by Hilton
See all 1,407 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Trenchtown holiday with Expedia?
Choose Expedia to plan your next big adventure simply and all in the same place. Our top tip for getting an unbeatable deal on a Trenchtown getaway? Bundle your flights, hotel and/or hire car into a package holiday. Then add some exciting tours and activities. Most bookings also come with flexible cancellation policies, so there’s no need to worry if you have to switch up your itinerary. Round-the-clock assistance with making tweaks to your trip is available via our Customer Service Portal link.
When is the best time of year to holiday in Trenchtown?
Into sightseeing but don’t like huge crowds? Plan your Trenchtown trip for November, December and January. Typically, it’s a lot quieter than in March, August and October. To give you an idea of what type of weather you can experience, the average temperature during the day in January, the coolest time of year in Trenchtown, is 24ºC. The warmest month here is July, when temperatures average 28ºC.
What is the top hotel for my holiday in Trenchtown?
Spanish Court Hotel - A Small Luxury Hotel is the perfect base for an unforgettable holiday in Trenchtown, offering all the comforts and amenities you need and more.
How do I get a cheap holiday to Trenchtown?
If you love bargains, bundle your bookings into a Trenchtown holiday. Whether you’re searching for flights, hotels, hire cars or day tours, you can book everything in one place. You’ll have loads of choice at your fingertips as well. Expedia has more than 400 partner airlines and 321,000 hotel options globally to take your pick of. Fly with who you prefer, stay anywhere you like and save a tidy sum — now that’s the perfect holiday! Learn more about how you can save money on your next holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Trenchtown holiday?
Make sure your holiday in Trenchtown is an unforgettable one by taking in its most popular attractions. National Gallery of Jamaica, Bob Marley Museum, Jamaica House and United States of America Embassy are among the things you should see while you’re in the city.
What is the best area to stay in when on holiday in Trenchtown?
Trenchtown has many fascinating places to discover, like Trench Town Culture Yard. Book accommodation near this attraction and make sightseeing stress-free.
Do I need a visa for my Trenchtown holiday?
Research the most up-to-date information on official government websites. Your nationality and whether you’re travelling for business, leisure or study will determine if you’ll require a visa for Trenchtown. Familiarise yourself with the application process, including any required documentation, fees and turnaround times. Submit your application well in advance to allow sufficient time for processing. Some visas can take many weeks or even months to obtain, depending on the country and time of year.
What should I wear on my Trenchtown holiday?
Although everyone’s personal style is different, it can help to have some guidelines for what to bring during your holiday in Trenchtown. We recommend browsing style blogs before you leave so you can blend in like a local. Pack appropriately by monitoring the forecast in Trenchtown. July brings the warmest temperatures, with daily averages of 28ºC, while January days average 24ºC, making it the coolest month.
What does an Expedia Trenchtown holiday include?
With Expedia, you can choose any combination of car hires, hotels and flights to build your ideal Trenchtown package. Once you’ve made your booking, simply add on all the fun stuff like day tours and activities. Remember, the more you bundle, the more discounts you’ll get! Apartments and private holiday homes are two popular property types in Trenchtown. Whatever your holiday style or group size, you can count on Expedia for the freedom and flexibility to customise your next escape.
Does Expedia offer Book Now, Pay Later Trenchtown holidays?
Yes. Expedia has teamed up with online lender Klarna to help you easily pay for your trip in manageable instalments. Simply select the payment plan that suits best during the checkout process and take the stress out of budgeting for your next trip. Make sure you bundle your flights, accommodation and car hire with Expedia to get the biggest bang for your buck. Check out our flexible payment options below:

  • Pay monthly holidays: If paying bite-sized amounts each month sounds best for you, Klarna offers just that! Paying in easy monthly instalments will make that dream holiday possible.
  • No-deposit holidays: Hitting the “book now” button is much easier with this plan. With no upfront fee for your holiday, you can Book Now, Pay Later and start packing your bags.

Can I choose my airline with a Trenchtown Expedia holiday?
You can. We offer more than 400 partner airlines throughout the world, so select the carrier that fits your budget and travel needs.

Popular places to visit

Image for Trench Town Culture Yard

Trench Town Culture Yard

You can enjoy some culture when you stop by Trench Town Culture Yard in Kingston. Visit the lively bars or top-notch restaurants in this relaxing area.

Trench Town Culture Yard
Image for Carib 5 Cinema

Carib 5 Cinema

Learn about the local history of Kingston when you take a trip to Carib 5 Cinema. Visit the top-notch restaurants or lively bars in this relaxing area.

Carib 5 Cinema
Image for Serenity Park

Serenity Park

Explore the great outdoors at Serenity Park, a lovely green space in Kingston. Visit the lively bars or top-notch restaurants in this relaxing area.

Serenity Park

Things to do

Image for 360 Degrees City to Mountain EcoTour Experience

360 Degrees City to Mountain EcoTour Experience

£475
Per adult
360 Degrees City to Mountain EcoTour Experience
Image for Private Bird watching Tour in Kingston Jamaica with Lunch

Private Bird watching Tour in Kingston Jamaica with Lunch

£142
Per adult
Private Bird watching Tour in Kingston Jamaica with Lunch
Image for Walking Tour in Kingston Jamaica with a Private Guide

Walking Tour in Kingston Jamaica with a Private Guide

£95
Per adult
Walking Tour in Kingston Jamaica with a Private Guide
See all activities in Kingston

More trip options

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.