Trenchtown Holidays from £681
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Your Trenchtown Holiday
From its highlights to its hidden delights, this city is best explored with a Trenchtown holiday package. Book a hotel in Spanish Town Zone, which is good for views, history and walking. Fill your spare time with visits to National Gallery of Jamaica, Bob Marley Museum and Jamaica House, some of the things you just have to see during your trip to Trenchtown. Stop daydreaming and start doing. Browse the broad range of options on Expedia today and finally put your Trenchtown holiday plans into gear!
Price found within the past 48 hours. Click for updated prices.
Casa Clayton at Donhead - New Kingston
New Kingston
£681
per person
2 Dec - 6 Dec
found 11 hours ago
Return direct flight included
Medellín (MDE) to Kingston (KIN)
10/10 Exceptional! (35 reviews)
Area around the property was beautiful and quiet. The property is a fire trap bar..around the windows with only one entrance door. In addition the kitcken is at the entrance the only waytoexisttheproperty. ......
.....bars
Reviewed on 9 Mar 2025
New Kingston Guest Apartments at Abbey
New Kingston
£713
per person
2 Dec - 6 Dec
found 11 hours ago
Return direct flight included
Medellín (MDE) to Kingston (KIN)
9/10 Wonderful! (20 reviews)
No one was available to check us in and no email was sent with instructions. The apartment looks ran down but on the picture it looks completely different. I was charged the rate and no yet was money refunded. Terrible service
Reviewed on 1 Nov 2025
New Kingston Guest Apartment at Westbury
New Kingston
£755
per person
2 Dec - 6 Dec
found 11 hours ago
Return direct flight included
Medellín (MDE) to Kingston (KIN)
9.6/10 Exceptional! (23 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
New Kingston Guest Apartment at Donhead
New Kingston
£1,523
per person
24 Oct - 31 Oct
found 1 day ago
Return flight included
London (LON) to Kingston (KIN)
9.6/10 Exceptional! (17 reviews)
Best value for money in Kingston. Safe, clean apartment with everything you need for self-catering and great air-conditioning and wi-fi. So close to the US Embassy, our trip went smoothly. Only issue is that check-in is very late and check-out is very early.
Reviewed on 21 Sept 2019
Where to stay in Trenchtown
Find the best Trenchtown areas and neighborhoods for the activities you enjoy most. Learn more about Trenchtown
New Kingston
2 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.
Port Royal
Explore the city where buccaneers and cutthroats once ruled. Learn about the earthquake that caused most of it to sink into the sea.
Half Way Tree
When in Half Way Tree, you can plan a visit to Devon House and Kings House, some noteworthy sights in the nearby area.
Constant Spring
1 out of top 10 points of interest in this area
If you're spending some time in Constant Spring, Manor Park Plaza and Constant Spring Golf Club are top sights worth seeing.
Liguanea
1 out of top 10 points of interest in this area
The restaurants and shopping are just a few features travellers like about Liguanea. If you want to do some sightseeing nearby, Bob Marley Museum and National Stadium are a few top places to visit.
Top hotels in Trenchtown
S Hotel Kingston
1 St Lucia Avenue Kingston Saint Andrew
Fully refundableReserve now, pay when you stay
£182
3 Oct - 4 Oct
includes taxes & fees
9.4/10 Exceptional! (1,777 reviews)
"The hotel was lovely and most of the staff were nice. A few times when we went to the front desk our questions seemed bothersome to the person who helped us. It didn't feel welcoming. The breakfast staff were lovely. Our dinner in the hotel was very expensive for not a lot of food. The atmosphere ..."
Reviewed on 21 Sept 2026
R Hotel Kingston
2 Renfrew Road , Kingston 10, Jamaica Kingston Jamaica
Fully refundableReserve now, pay when you stay
£156
25 Oct - 26 Oct
includes taxes & fees
8.4/10 Very good! (1,178 reviews)
"I stayed for one night the staff were perlite the Building and room was clean... it was slightly noisy up untill around 1.00 and i can say is it was a bit disappointing there wasn't any usb port facility in the room."
Reviewed on 24 Sept 2026
ROK Hotel Kingston, Tapestry Collection by Hilton
2-4 King Street Kingston
Fully refundableReserve now, pay when you stay
£156
2 Oct - 3 Oct
includes taxes & fees
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.
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.
Stay near popular Trenchtown attractions
Trench Town Culture Yard
Enjoy an outing to Trench Town Culture Yard during your stay in Kingston. Visit the top-notch restaurants or lively bars in this relaxing area.
Carib 5 Cinema
Learn about the local history of Kingston when you take a trip to Carib 5 Cinema. Visit the lively bars or top-notch restaurants in this family-friendly area.
Serenity Park
Explore the great outdoors at Serenity Park, a lovely green space in Kingston. Visit the top-notch restaurants or lively bars in this relaxing area.
Wynter's Park
Explore the great outdoors at Wynter's Park, a lovely green space in Kingston. Visit the top-notch restaurants or lively bars in this relaxing area.
Things to do
Kingston Blue Mountains Tour with Coffee Tasting
£66
per adult
100% of travellers recommend
Kingston Tour & Bob Marley Museum Admission
£59
per adult
74% of travellers recommend
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* 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.