Trenchtown Vacations from $591

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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!

The Latest Trenchtown Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Halifax Guest Apartment

The Halifax Guest Apartment

3.5 out of 5
Save 100% on your flight
Price was $1,071, price is now $591 per person
$591
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Kingston (KIN)
9.6/10 Exceptional! (4 reviews)
Modern London Decor Guest Apartments

Modern London Decor Guest Apartments

3.5 out of 5
Barbican
Save 100% on your flight
Price was $1,159, price is now $613 per person
$613
per person
Oct 13 - Oct 17
found 11 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Kingston (KIN)
6.8/10 (5 reviews)
New Kingston Guest Apartment at Donhead

New Kingston Guest Apartment at Donhead

3 out of 5
New Kingston
Save 100% on your flight
Price was $1,185, price is now $658 per person
$658
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Kingston (KIN)
8.4/10 Very Good! (20 reviews)
The Guest Apartments at Border Crossings

The Guest Apartments at Border Crossings

4.5 out of 5
Havendale
Save 100% on your flight
Price was $1,056, price is now $594 per person
$594
per person
Oct 30 - Nov 4
found 3 hours ago
Roundtrip non-stop flight included
New York (NYC) to Kingston (KIN)
4/10 (1 review)
Chancery Hall 3 Bedroom Apartment

Chancery Hall 3 Bedroom Apartment

3 out of 5
Save 100% on your flight
Price was $1,072, price is now $635 per person
$635
per person
Sep 27 - Oct 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Kingston (KIN)
No reviews

Where to stay in Trenchtown

Find the best Trenchtown areas and neighborhoods for the activities you enjoy most. Learn more about Trenchtown
Devon House which includes 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

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
$162 nightly
The price is $188 total per night from Sep 6 to Sep 7
$188 total
Sep 6 - Sep 7
Total with taxes and fees
9.2/10 Wonderful! (1,463 reviews)
"It was very nice and very clean and comfortable"

Reviewed on Aug 23, 2025

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
$159 nightly
The price is $177 total per night from Sep 4 to Sep 5
$177 total
Sep 4 - Sep 5
Total with taxes and fees
8.8/10 Excellent! (1,064 reviews)
"It was a really nice hotel !"

Reviewed on Aug 20, 2025

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
$176 nightly
The price is $192 total per night from Sep 24 to Sep 25
$192 total
Sep 24 - Sep 25
Total with taxes and fees
8.4/10 Very Good! (1,160 reviews)
R Hotel is the best.
"My stay was great. The staff in housekeeping were awesome and very friendly. The breakfast, lunch and dinner crew were excellent, polite and courteous. This was my third time staying at the R Hotel."

Reviewed on Aug 22, 2025

R Hotel Kingston
See all 1,530 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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Trenchtown

Trench Town Culture Yard

You can spend an afternoon browsing the exhibits at Trench Town Culture Yard during your trip to Kingston. Check out the top-notch restaurants or lively bars in this relaxing area.

Trench Town Culture Yard

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

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.

Serenity Park

Things to do

Walk Tours in Kingston.

Walk with me in Kingston/Port Royal

$60
per adult
Walk with me in Kingston/Port Royal
Mural Tours in the Downtown Kingston Art District, Jamaica

Mural Tours in the Downtown Kingston Art District, Jamaica

$40
per adult
Mural Tours in the Downtown Kingston Art District, Jamaica
The Capital City Kingston Tour

The Capital City Kingston Tour

$120
per adult
The Capital City Kingston Tour
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.