Jackson Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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

Top hotels in Jackson

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort

5 out of 5
End of Belair Road Long Bay St. Philip
Fully refundableReserve now, pay when you stay
The price is S$667 per night from 13 Aug to 14 Aug
S$667
13 Aug - 14 Aug
includes taxes & fees
7.8/10 Good! (727 reviews)
"Everything was lovely"

Reviewed on 15 Jul, 2026

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort
Hilton Grand Vacations Club The Crane Barbados

Hilton Grand Vacations Club The Crane Barbados

4.5 out of 5
The Crane Resort Diamond Valley
Fully refundable
The price is S$248 per night from 27 Jul to 28 Jul
S$248
27 Jul - 28 Jul
includes taxes & fees
8.6/10 Excellent! (604 reviews)
"Staff was welcoming and hotel was clean"

Reviewed on 17 Jul, 2026

Hilton Grand Vacations Club The Crane Barbados
Divi Southwinds Beach Resort

Divi Southwinds Beach Resort

3 out of 5
St Lawrence Main Road St. Lawrence Gap Christ Church
Fully refundableReserve now, pay when you stay
The price is S$202 per night from 4 Aug to 5 Aug
S$202
4 Aug - 5 Aug
includes taxes & fees
8/10 Very good! (868 reviews)
"Amazing staff from the moment we checked in. Stayed 8 days and would stay here again."

Reviewed on 15 Jul, 2026

Divi Southwinds Beach Resort
See all 3,546 properties in Jackson
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.

What to do in Jackson

Luxury Evening Voyage - All-Inclusive Coastal Cruise By Oceanluxx

Luxury Evening Voyage - All-Inclusive Coastal Cruise By Oceanluxx

S$136
per adult
100% of travellers recommend
Luxury Evening Voyage - All-Inclusive Coastal Cruise By Oceanluxx
Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise

Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise

S$110
per adult
96% of travellers recommend
Barbados Catamaran Turtle and Shipwreck Snorkeling Cruise
Cave & Monkey Zipline Experience at Harrison's Cave by Chukka

Harrison's Cave Tour & Monkey Zipline, Barbados

S$174
per adult
90% of travellers recommend
Harrison's Cave Tour & Monkey Zipline, Barbados
See all activities in Jackson

Frequently asked questions

How much does a Jackson holiday package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a holiday to Jackson costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Jackson?
The off-season is the best time to travel to Jackson if you're on a budget. Another tip for getting cheap Jackson holiday packages? Avoid visiting during public holidays and any major events.
How many days is enough for Jackson?
With a well-organised travel plan, you can easily hit the main Jackson attractions in a few days. But if you prefer to discover lesser-known spots or go on day tours, consider booking your Jackson holiday for longer.
How to find the best Jackson package deals?
Begin your search for a Jackson package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Jackson package deal right away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Jackson getaway off to a flying start.
Is it cheaper to book a Jackson holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still have the freedom to create a customised Jackson holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday package to Jackson?
If you're considering a spontaneous Jackson adventure, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Jackson?

  1. Choose when to travel: Check your schedule and get packing. Your favourite time of year and the type of activities on offer will also help you decide when to visit Jackson.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and meals to flights and experiences. Your hotel will likely be the biggest expense during your trip to Jackson.
  3. Decide how long to go away for: Now that you're more familiar with Jackson, you can work out the right length of your break. Put together a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Jackson holiday package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.