Trenchtown Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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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.
Eclipse Suite Guest Apartments

Eclipse Suite Guest Apartments

3.5 out of 5
Havendale
Price was CA $2,116, price is now CA $1,153 per person
CA $1,153
per person
Jul 2 - Jul 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Kingston (KIN)
9.2/10 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 Jul 12, 2019

New Kingston Guest Apartment at Westbury

New Kingston Guest Apartment at Westbury

3.5 out of 5
New Kingston
Price was CA $2,707, price is now CA $1,434 per person
CA $1,434
per person
Jul 6 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) 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 Nov 13, 2022

Modern London Decor Guest Apartments

Modern London Decor Guest Apartments

3.5 out of 5
Barbican
Price was CA $2,441, price is now CA $1,296 per person
CA $1,296
per person
Jul 2 - Jul 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Kingston (KIN)
8/10 Very Good! (4 reviews)
Perfect location in Kingston. Felt secure at all times.

Reviewed on Dec 16, 2019

Casa Clayton at Donhead - New Kingston

Casa Clayton at Donhead - New Kingston

3.5 out of 5
New Kingston
Price was CA $2,217, price is now CA $1,177 per person
CA $1,177
per person
Jul 2 - Jul 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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 Corporate Apts at Donhead

New Kingston Corporate Apts at Donhead

3.5 out of 5
New Kingston
Price was CA $2,227, price is now CA $1,202 per person
CA $1,202
per person
Jul 2 - Jul 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Kingston (KIN)
9.6/10 Exceptional! (31 reviews)
Wow, we rented this accommodations for Jamaica carnival and was very lucky. It was 5 minutes away from the Bob Marley Museum. 10 minutes from Devon house, the best ice-cream in Jamaica. It was very centrally located where we weren't far from anything. The unit itself is spotless and clean. It was a very well kept unit. QUICK callout to please call them 72 hours in advance to give them the heads up that you're checking in. That was the only quirky step. The unit also had a washer and dryer.

Reviewed on May 5, 2025

Where to stay in Trenchtown

Find the best Trenchtown areas and neighborhoods for the activities you enjoy most. Learn more about Trenchtown
New Kingston

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.

Find hotels in New Kingston

Trenchtown Hotel Deals

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 CA $241 per night from May 15 to May 16
CA $241
CA $305 total
May 15 - May 16
includes taxes & fees
9.4/10 Exceptional! (1,662 reviews)
Great hotel and convenient. Close to everything. Staff was excellent as well.

Reviewed on Apr 14, 2026

S Hotel Kingston
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 CA $225 per night from May 11 to May 12
CA $225
CA $277 total
May 11 - May 12
includes taxes & fees
8.8/10 Excellent! (1,227 reviews)
The breakfast was was amazing and staffs was excellent

Reviewed on Apr 14, 2026

ROK Hotel Kingston, Tapestry Collection by Hilton
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 CA $207 per night from May 7 to May 8
CA $207
CA $254 total
May 7 - May 8
includes taxes & fees
8.4/10 Very Good! (1,169 reviews)
The rooms were absolutely spotless. Large and spacious and we got some amazing upgraded rooms. The breakfast was amazing. I would definitely go back.

Reviewed on Apr 13, 2026

R Hotel Kingston
See all 1,571 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 vacation package cost?
Be ready to book, because a trip to Trenchtown starts from only CA $1,153. 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.

Discover the most popular places to visit in Trenchtown

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 relaxing area.

Carib 5 Cinema

Things to do

Kingston Dub Club Sundays

Kingston Dub Club Sundays

CA $89
per adult
Kingston Dub Club Sundays
displays at the bob marley museum in Jamaica

Kingston Tour & Bob Marley Museum Admission

CA $111
per adult
74% of travellers recommend
Kingston Tour & Bob Marley Museum Admission
Kingston: Story of Jamaican Music Tour including Entry Fees

Kingston: Story of Jamaican Music Tour including Entry Fees

CA $123
per adult
100% of travellers recommend
Kingston: Story of Jamaican Music Tour including Entry Fees
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.