Trenchtown Vacation Packages
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Your Trenchtown Vacation
From its highlights to its hidden delights, this city is best explored with a Trenchtown vacation 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 vacation plans into gear!
Top Holiday Package Deals in Trenchtown
Price found within the past 48 hours. Click for updated prices.
Casa Clayton at Donhead - New Kingston
New Kingston
CA $1,161
per person
Nov 24 - Dec 1
found 24 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) 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 Mar 9, 2025
New Kingston Guest Apartment VII
Liguanea
CA $1,955
per person
Nov 29 - Dec 6
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Kingston (KIN)
10/10 Exceptional! (8 reviews)
This is a great place for anyone who likes their privacy. They have all of the amenities and the apartment was is in a nice community. Highly recommended!
Reviewed on Aug 21, 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
3 out of top 10 points of interest in this area
Discover urban parks like Emancipation Park and Hope Gardens, or explore landmarks such as the Bob Marley Museum. Enjoy the redeveloped waterfront area with hotels, shops, and cultural centers, while easily navigating via buses and taxis.
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
Half Way Tree might not have many top sights, but Devon House and Kings House are two attractions nearby that you can check out.
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.
Mona Heights
Mona Heights is well-liked for its restaurants and shopping. If you're hoping to see more of the larger area, Hope Zoo and National Stadium are some interesting sights nearby to check out.
Trenchtown Hotel Deals
S Hotel Kingston
1 St Lucia Avenue Kingston Saint Andrew
Fully refundableReserve now, pay when you stay
CA $264
CA $340 total
Sep 18 - Sep 19
includes taxes & fees
9.4/10 Exceptional! (1,776 reviews)
"Beautiful interior, relaxing ambiance, great Jamaican breakfast each morning and the staff provide excellent customer service. We will be returning next year."
Reviewed on Sep 17, 2026
R Hotel Kingston
2 Renfrew Road , Kingston 10, Jamaica Kingston Jamaica
Fully refundableReserve now, pay when you stay
CA $240
CA $295 total
Sep 20 - Sep 21
includes taxes & fees
ROK Hotel Kingston, Tapestry Collection by Hilton
2-4 King Street Kingston
Fully refundableReserve now, pay when you stay
CA $237
CA $292 total
Oct 2 - Oct 3
includes taxes & fees
8.8/10 Excellent! (1,285 reviews)
"It was an ok stay, wouldn't come back though."
Reviewed on Sep 17, 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 vacation package cost?
Be ready to book, because a trip to Trenchtown starts from only CA $1,161. When you bundle your flights, hotels and car rentals into a vacation package, you'll enjoy the best deals.
How do I get a cheap travel package to Trenchtown?
Our Trenchtown vacation 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 vacation 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 vacation?
Travelers 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 vacation package is the most convenient way to organize 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 vacation package?
Yes — that's one of the best things about an Expedia vacation 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 vacation 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 vacation 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. Check out 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. Check out the lively bars or top-notch restaurants in this family-friendly area.
Wynter's Park
Explore the great outdoors at Wynter's Park, a lovely green space in Kingston. Check out the top-notch restaurants or lively bars in this relaxing area.
Serenity Park
Explore the great outdoors at Serenity Park, a lovely green space in Kingston. Check out the top-notch restaurants or lively bars in this relaxing area.
Things to do
Kingston Blue Mountains Tour with Coffee Tasting
CA $125
per adult
100% of travellers recommend
Kingston Tour & Bob Marley Museum Admission
CA $112
per adult
74% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.