Trenchtown Trip
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Price found within the past 48 hours. Click for updated prices.
Shirley Retreat Hotel
New Kingston
₹147,356
per person
3 Jan - 9 Jan
found 11 hours ago
Return flight included
Winnipeg (YWG) to Kingston (KIN)
8.4/10 Very good! (580 reviews)
My experience was not a good one. Room was not properly clean especially the floor. A/C was not working during my stay I almost passed out from the heat. The WiFi sucks! It kept going in and out, very weak . I reported the problem to the front desk yet they did Nothing! I would never recommend this place yo anyone. Also the customer service was poor except for that one lady I spoke to on my way out. She was very nice to us. She did apologized to us for the inconvenience.
Reviewed on 30 Sept 2026
Lagardan Ocean View
₹251,258
per person
3 Jan - 9 Jan
found 11 hours ago
Return flight included
Winnipeg (YWG) to Kingston (KIN)
10/10 Exceptional! (1 review)
My stay at the Laguardan Ocean View was excellent. I wanted to try somewhere new from where I usually stay and I was very impressed. The place is clean, quiet, comfortable security is excellent and you feel like you’re home. Just in case you’re not driving it’s also on the bus and taxi route so no problem there. Everyone is friendly and inviting. I would definitely recommend this beautiful place for anyone to stay while visiting Jamaica, I had a great time staying here.
Reviewed on 15 Aug 2019
The Courtleigh Hotel and Suites
New Kingston
₹182,219
per person
3 Jan - 9 Jan
found 11 hours ago
Return flight included
Winnipeg (YWG) to Kingston (KIN)
9.2/10 Wonderful! (1,014 reviews)
One of the best hotels I have ever stay with. If you want good food, nice views and communicate with great people... Courtleigh Hotel is the best hotel
Reviewed on 10 Oct 2026
Where to stay in Trenchtown
Find the best Trenchtown areas and neighborhoods for the activities you enjoy most. Learn more about Trenchtown
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.
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.
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.
Constant Spring
If you're spending some time in Constant Spring, Manor Park Plaza and Constant Spring Golf Club are top sights worth seeing.
Top hotels in Trenchtown
S Hotel Kingston
1 St Lucia Avenue Kingston Saint Andrew
Fully refundableReserve now, pay when you stay
₹18,283
₹23,515 total
8 Nov - 9 Nov
includes taxes & fees
R Hotel Kingston
2 Renfrew Road , Kingston 10, Jamaica Kingston Jamaica
Fully refundableReserve now, pay when you stay
₹18,065
₹22,136 total
23 Oct - 24 Oct
includes taxes & fees
AC Hotel by Marriott Kingston, Jamaica
38 Lady Musgrave Rd Kingston St. Andrew Parish
Fully refundableReserve now, pay when you stay
₹22,118
₹27,814 total
31 Oct - 1 Nov
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Everything 10/10. Only place I stay when in Kingston!"
Reviewed on 10 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.
Frequently asked questions
How much does a Trenchtown holiday package cost?
Be ready to book, because a trip to Trenchtown starts from only ₹147,356. 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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.