Half Way Tree Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Price found within the past 48 hours. Click for updated prices.
  • Outdoor pool
    Aug 14 - Aug 24

    The Country Club Villa II + Flight

    Kingston
    10 nights
    3.5 star property
    8.2/10 - Very good (13 reviews)
    "Special instructions was not clear before booking couldn’t get a refund from host after host said they will refund the money. Place is crooked"
    Reviewed April 13, 2026
    Roundtrip • Hamilton (YHM) - Kingston (KIN)
    YHM - KIN • 1 stop KIN - YHM • 1 stop
    CA $3,048
    CA $1,660
    per traveller
    found 18 hours ago
    The Country Club Villa II
  • Family Apartment, Mountain View | Bathroom
    Jul 8 - Jul 17

    Kingston Luxury Family Retreat + Flight

    Jack's Hill
    9 nights
    3.5 star property
    Roundtrip • Toronto (YYZ) - Kingston (KIN)
    YYZ - KIN • Nonstop KIN - YYZ • Nonstop
    CA $5,778
    CA $2,849
    per traveller
    found 4 hours ago
    Kingston Luxury Family Retreat
  • Garden
    Jul 8 - Jul 17

    The View of Devon House + Flight

    Half Way Tree
    9 nights
    3.0 star property
    Roundtrip • Toronto (YYZ) - Kingston (KIN)
    YYZ - KIN • Nonstop KIN - YYZ • Nonstop
    CA $3,265
    CA $1,722
    per traveller
    found 4 hours ago
    The View of Devon House
  • Inn Seaclusion
    Jul 17 - Jul 27

    Sea Cliff Resort + Flight

    Long Bay
    10 nights
    3.0 star property
    8.2/10 - Very good (202 reviews)
    "Sea cliff's property was beautiful and my partner and I have an amazing time on the quiet property. The rooms were clean and the housekeeping came every morning. We do wish the air conditioner was more efficient and cooled the entire room, it only cooled one side. The lunch/dinner was great, it was a little expensive than usual. Free breakfast is included and that was a big plus. The staff was super attentive to our needs and super respectful."
    Reviewed May 26, 2026
    Roundtrip • Hamilton (YHM) - Kingston (KIN)
    YHM - KIN • 1 stop KIN - YHM • 1 stop
    CA $3,325
    CA $1,782
    per traveller
    found 18 hours ago
    Sea Cliff Resort
  • Exterior
    Jul 7 - Jul 21

    Top Brass Ocean View Vacation Rental + Flight

    Boscobel
    14 nights
    3.0 star property
    10/10 - Exceptional (1 review)
    "The hotel and the staff was nice .Great acomadation total relaxation and a great location over looking the ocean. Great place to stay five stars all the way..."
    Reviewed March 17, 2017
    Roundtrip • Hamilton (YHM) - Montego Bay (MBJ)
    YHM - MBJ • 1 stop MBJ - YHM • 1 stop
    CA $4,739
    CA $2,586
    per traveller
    found 1 day ago
    Top Brass Ocean View Vacation Rental

Where to stay in Half Way Tree

Find the best Half Way Tree areas and neighborhoods for the activities you enjoy most. Learn more about Half Way Tree
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

Half Way Tree Hotel Deals

Terra Nova, BW Premier Collection

Terra Nova, BW Premier Collection

4 out of 5
17 Waterloo Road Kingston Saint Andrew
Fully refundableReserve now, pay when you stay
The price is CA $280 per night from Jun 5 to Jun 6
CA $280
CA $337 total
Jun 5 - Jun 6
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"I would give the Terra Nova 3 stars. The main reason for this lower rating was the state of the bathroom, the toilet had a clear seal applied right over a layer of black grime, leaving it looking absolutely dirty. For a high-end hotel, I definitely expected a much higher standard of cleanliness and ..."

Reviewed on May 23, 2026

Terra Nova, BW Premier Collection
Apartment with roof top pool

Apartment with roof top pool

2 out of 5
20 South Ave Kingston St. Andrew Parish
The price is CA $228 per night from Jun 4 to Jun 5
CA $228
CA $414 total
Jun 4 - Jun 5
includes taxes & fees
9/10 Wonderful! (7 reviews)
"Excellent service. Great location."

Reviewed on May 30, 2026

Apartment with roof top pool
New Kingston's Deluxe Apartment

New Kingston's Deluxe Apartment

3.5 out of 5
Surbiton Road Kingston
8.6/10 Excellent! (66 reviews)
"This is not personal but please stay somewhere else! The community is gated which is great! However at 11am I called asked about early check-in and the address as I could not get to customs without an address she gave me a random address and told me she would have someone reach out about the early ..."

Reviewed on May 25, 2026

Get rates
New Kingston's Deluxe Apartment
See all 1,610 properties in Half Way Tree
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 Half Way Tree vacation package cost?
Starting from as low as , you can tailor make your Half Way Tree package the way you want. Simply bundle hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Half Way Tree?
Browse and lock in everything all in one place with our Half Way Tree vacation packages. We have incredible bargains on hotels, flights, tours and more that'll keep your pocket happy and your adventurous spirit busy. And, with more than 550 air carriers and 1,000,000 hotel options across the globe to select from, you'll have the flexibility to mix and match however you please.
Where should I stay in Half Way Tree?
If you're itching to be in the center of the action, stay close to National Gallery of Jamaica. Many happy campers book a hotel around this renowned attraction.
What are the top hotels in Half Way Tree?
Book a stay at 2 Bedroom Townhouse At Surbiton Square. It's one of this area's most in-demand hotels. Another top option in Half Way Tree is Harloes Place.
How far in advance should I book my Half Way Tree vacation?
It all depends on the airline, but it's usually possible to browse through international fares on Expedia up to 12 months in advance. While it's generally recommended to book ahead of time, lucky customers will sometimes score a cheaper flight only weeks before the date of departure.
What does an Expedia Half Way Tree travel package include?
You can choose from any combination of flights, rental cars and hotels. Once you've made your booking, you can also add on tours and experiences. Want to pick your fare class? That's possible too. The choice is all yours when it comes to putting together your dream Half Way Tree getaway.
What should I know before booking a Half Way Tree travel package?
Locking in all the parts of your getaway together is one of the easiest ways to save. Combine your airfares, rental cars and hotels into a convenient package. But you're not limited to hotels. Expedia features all types of properties, including vacation rentals like oceanfront condos and spacious residences. You've got choices galore!
Can I choose my airline with a Half Way Tree Expedia vacation package?
Expedia has access to more than 550 airline partners globally, so you certainly can. Simply select your preferred carrier and put together the perfect Half Way Tree vacation.
If I'm not able to travel, can I cancel my Half Way Tree vacation package?
Your situation can change suddenly, so yes. You may be able to amend or cancel your Half Way Tree vacation package at no cost if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still make the necessary changes, but your airline, hotel or car rental company may charge additional fees. Looking for more information? Visit our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.

Discover the most popular places to visit in Half Way Tree

Bob Marley Museum

Bob Marley Museum

Learn how a poor Jamaican man from Trench Town became an international pop star thanks to his thought-provoking lyrics and feel-good reggae music.

Bob Marley Museum
Devon House

Devon House

Explore the opulent home of Jamaica’s first black millionaire, go shopping and sample the famous ice cream in the mansion’s courtyard.

Devon House
Emancipation Park

Emancipation Park

Take a morning jog, enjoy pleasant tropical scents or admire the artwork in Kingston’s favorite park, a tribute to Jamaican residents’ journey to freedom.

Emancipation Park

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.