Title: Trenchtown Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,010 Expedia.ca

[Trenchtown Travel Guide](https://expedia.ca/Kingston-Trenchtown.dx6004109)[Hotels in Trenchtown](https://expedia.ca/Trenchtown-Kingston-Hotels.0-n6004109-0.Travel-Guide-Filter-Hotels)[Flights to Kingston](https://expedia.ca/Cheap-Flights-To-Kingston.d180034.Travel-Guide-Flights)[Things to do in Kingston](https://expedia.ca/Things-To-Do-In-Kingston.d180034.Travel-Guide-Activities)[Trenchtown Car Rentals](https://expedia.ca/Car-Rentals-In-Trenchtown.d6004109.Car-Rental-Guide)

![](https://images.trvl-media.com/place/1820/2587ea8c-9596-47c1-bbbf-c183cd96ef83.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Trenchtown Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

Photo by Zinzi Samuels

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

#### 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](https://www.expedia.ca/National-Gallery-Of-Jamaica-Kingston.d6086247.Vacation-Attraction), [Bob Marley Museum](https://www.expedia.ca/Bob-Marley-Museum-Kingston.d501396.Vacation-Attraction) and [Jamaica House](https://www.expedia.ca/Jamaica-House-Kingston.d553248621533157726.Vacation-Attraction), 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](https://images.trvl-media.com/lodging/20000000/19730000/19727600/19727548/af01dd41_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Casa Clayton at Donhead - New Kingston

New Kingston

CA $1,010

per person

Apr 11 - Apr 17

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Kingston (KIN)

9.6/10 Exceptional! (37 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 Apt at Fairway](https://images.trvl-media.com/lodging/20000000/19110000/19105300/19105255/e122acaf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### New Kingston Guest Apt at Fairway

New Kingston

CA $1,724

per person

Apr 11 - Apr 17

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Kingston (KIN)

No reviews

![Modern London Decor Guest Apartments](https://images.trvl-media.com/lodging/17000000/16110000/16104800/16104769/aa6959ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Modern London Decor Guest Apartments

Barbican

CA $1,238

per person

Apr 10 - Apr 17

found 20 hours ago

Roundtrip flight included

Toronto (YTO) to Kingston (KIN)

6/10 (6 reviews)

Perfect location in Kingston. Felt secure at all times.

Reviewed on Dec 16, 2019

![New Kingston Corporate Apts at Donhead](https://images.trvl-media.com/lodging/20000000/19730000/19726500/19726475/61ea0b48_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### New Kingston Corporate Apts at Donhead

New Kingston

CA $1,105

per person

Apr 10 - Apr 17

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

![New Kingston Guest Apartment VII](https://images.trvl-media.com/lodging/17000000/16730000/16720600/16720538/45ba32d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### New Kingston Guest Apartment VII

Liguanea

CA $1,971

per person

Apr 10 - Apr 17

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Kingston (KIN)

9/10 Wonderful! (10 reviews)

## Where to stay in Trenchtown

Find the best Trenchtown areas and neighborhoods for the activities you enjoy most. [Learn more about Trenchtown](https://expedia.ca/Kingston-Trenchtown.dx6004109)

![Devon House featuring a house and a garden](https://images.trvl-media.com/place/6159768/74089215-18a5-4422-9cb2-d71a455dce90.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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 hotel + flight trips in New Kingston](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=New%20Kingston&DestID=6004108&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Aerial View of Caribbean City Center, Half Way Tree, St. Andrew Jamaica.](https://images.trvl-media.com/place/553248635975847411/794e6934-7ecd-4dad-9077-74b1796e073c.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Half Way Tree

 Half Way Tree might not have many top sights, but Devon House and Jamaica House are two attractions nearby that you can check out. 

[Find hotel + flight trips in Half Way Tree](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Half%20Way%20Tree&DestID=553248635975847411&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Port Royal which includes a bay or harbour, boating and general coastal views](https://images.trvl-media.com/place/6004111/f14a49e7-3113-47b7-9cd0-8c44738b527a.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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. 

[Find hotel + flight trips in Port Royal](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Port%20Royal&DestID=6004111&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![The vast blue mountain range extending towards the horizon of Jamaica](https://images.trvl-media.com/place/553248635976400454/10fc190d-efab-4615-8391-c355254dfe65.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Barbican

4.5/5(3 area reviews)

 Barbican might not have many top sights, but Bob Marley Museum and Jamaica House are two attractions nearby that you can check out. 

[Find hotel + flight trips in Barbican](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Barbican&DestID=553248635976400454&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Great House owned by one of the first Black Millionaires of Jamaica](https://images.trvl-media.com/place/553248635976393478/9eefff62-5f3c-4c35-af0c-2bde4b085140.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Constant Spring

 If you're spending some time in Constant Spring, Manor Park Plaza and Constant Spring Golf Club are top sights worth seeing. 

[Find hotel + flight trips in Constant Spring](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Constant%20Spring&DestID=553248635976393478&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Trenchtown Hotel Deals

![S Hotel Kingston](https://images.trvl-media.com/lodging/3000000/2460000/2450100/2450088/57e4091f_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

S Hotel Kingston

1 St Lucia Avenue Kingston Saint Andrew

Fully refundableReserve now, pay when you stay

CA $271

CA $349 total

Feb 15 - Feb 16

includes taxes & fees

9.2/10 Wonderful! (1,624 reviews)

Greet service

Reviewed on Feb 3, 2026

[](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=2450088&PinnedHotelID=2450088&HadPinnedHotel=true&regionId=6004109)

![ROK Hotel Kingston, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/72000000/71560000/71554900/71554883/3213ca97_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

ROK Hotel Kingston, Tapestry Collection by Hilton

2-4 King Street Kingston 

Fully refundableReserve now, pay when you stay

CA $205

CA $254 total

Mar 6 - Mar 7

includes taxes & fees

8.8/10 Excellent! (1,181 reviews)

yes

Reviewed on Feb 3, 2026

[](https://expedia.ca/Hotel-Search?startDate=06%2F03%2F2026&endDate=07%2F03%2F2026&selected=71554883&PinnedHotelID=71554883&HadPinnedHotel=true&regionId=6004109)

![R Hotel Kingston](https://images.trvl-media.com/lodging/19000000/18990000/18989600/18989524/a675b6b0_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

R Hotel Kingston

2 Renfrew Road , Kingston 10, Jamaica Kingston Jamaica

Fully refundableReserve now, pay when you stay

CA $228

CA $280 total

Feb 9 - Feb 10

includes taxes & fees

8.4/10 Very Good! (1,166 reviews)

Arriving at the R I was pleasantly surprised by the cleanliness and the pleasant staff.I had actually come here for lunch-before and it was delicious,!They didn’t disappoint,breakfast was superb.My kitchenette was clean and had all the necessities.If you need to cook carry a small pot or frying pan.But ...

Reviewed on Jan 29, 2026

[](https://expedia.ca/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=18989524&PinnedHotelID=18989524&HadPinnedHotel=true&regionId=6004109)

[See all 1,564 properties in Trenchtown](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=05%2F02%2F2026&endDate=06%2F02%2F2026&regionId=6004109)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Frequently asked questions

### How much does a Trenchtown vacation package cost?

### How do I get a cheap travel package to Trenchtown?

### Where should I stay in Trenchtown?

### How far in advance should I book my Trenchtown vacation?

### What does an Expedia Trenchtown travel package include?

### What should I know before booking a Trenchtown travel package?

### Can I choose my airline with a Trenchtown Expedia vacation package?

### If I'm not able to travel, can I cancel my Trenchtown vacation package?

### 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 family-friendly area. 

[](https://expedia.ca/Carib-5-Cinema-Trenchtown.d553248621533157714.Vacation-Attraction)

### Things to do

![Kingston Dub Club Sundays](https://mediaim.expedia.com/localexpert/1243245/800fdb7b-6118-4894-8f65-0041c3b6fb98.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Kingston Dub Club Sundays

CA $90

per adult

[](https://expedia.ca/things-to-do/kingston-dub-club-sundays.a1243245.activity-details)

![displays at the bob marley museum in Jamaica ](https://mediaim.expedia.com/localexpert/209875/2381d49c-671d-43f6-b7c8-60b9c987e5ed.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Kingston Tour & Bob Marley Museum Admission

CA $112

per adult

**74%** of travellers recommend

[](https://expedia.ca/things-to-do/kingston-tour-bob-marley-museum-admission.a209875.activity-details)

![Kingston: Story of Jamaican Music Tour including Entry Fees](https://mediaim.expedia.com/localexpert/48826881/59b1d582-dcd4-4635-9121-3d11db2e7883.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Kingston: Story of Jamaican Music Tour including Entry Fees

CA $125

per adult

**100%** of travellers recommend

[](https://expedia.ca/things-to-do/kingston-story-of-jamaican-music-tour-including-entry-fees.a48826881.activity-details)

[See all activities in Kingston](https://expedia.ca/things-to-do/search?rid=6004109)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.