Trenchtown Vacation Packages

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  • Better together

    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.
Casa Royale Guest Apartment

Casa Royale Guest Apartment

3.5 out of 5
Molynes Gardens
Price was CA $2,017, price is now CA $996 per person
CA $996
per person
May 22 - May 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Kingston (KIN)
9.6/10 Exceptional! (68 reviews)
Place was very clean and comfortable.

Reviewed on Feb 8, 2023

New Kingston Guest Apt at Fairway

New Kingston Guest Apt at Fairway

3.5 out of 5
New Kingston
Price was CA $4,180, price is now CA $1,902 per person
CA $1,902
per person
Apr 24 - May 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Kingston (KIN)
No reviews
Kingston Luxury Family Retreat

Kingston Luxury Family Retreat

3.5 out of 5
Jack's Hill
Price was CA $4,506, price is now CA $2,219 per person
CA $2,219
per person
Apr 24 - May 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Kingston (KIN)
No reviews
Millsborough Guest Apartments

Millsborough Guest Apartments

3.5 out of 5
Jack's Hill
Price was CA $2,529, price is now CA $1,265 per person
CA $1,265
per person
Apr 13 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Kingston (KIN)
No reviews
New Kingston Corporate Apts at Donhead

New Kingston Corporate Apts at Donhead

3.5 out of 5
New Kingston
Price was CA $2,099, price is now CA $1,069 per person
CA $1,069
per person
May 24 - May 30
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YUL) 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
Devon House featuring a house and a garden

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

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 $229 per night from Mar 21 to Mar 22
CA $229
CA $282 total
Mar 21 - Mar 22
includes taxes & fees
8.8/10 Excellent! (1,180 reviews)
I enjoyed the stay overnight and appreciate the cultured design. I felt safe .

Reviewed on Mar 3, 2026

ROK Hotel Kingston, Tapestry Collection by Hilton
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 $266 per night from Mar 31 to Apr 1
CA $266
CA $343 total
Mar 31 - Apr 1
includes taxes & fees
9.4/10 Exceptional! (1,636 reviews)
Great

Reviewed on Mar 3, 2026

S Hotel Kingston
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 $214 per night from Apr 1 to Apr 2
CA $214
CA $263 total
Apr 1 - Apr 2
includes taxes & fees
8.4/10 Very Good! (1,173 reviews)
Rooftop bar and restaurant was great. Staff were friendly, polite and helpful. Wish we could have stayed longer.

Reviewed on Mar 3, 2026

R Hotel Kingston
See all 1,569 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Trenchtown vacation package cost?
Be ready to book, because a trip to Trenchtown starts from only CA $996. 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 top-notch restaurants or lively bars 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.