Cheapside Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to NT$5,067 when you book a flight and hotel together*
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    Find the right fit

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

    Plan, book, and manage your trip all in one place

Find the Best Cheapside Vacation Packages

Cheapside Hotel Deals

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 NT$13,977 per night from Jul 12 to Jul 13
NT$13,977
NT$15,655 total
Jul 12 - Jul 13
includes taxes & fees
7.6/10 Good! (431 reviews)
"The property was beautiful and well kept. The food and dining were great. There were a lot of activities and entertainment. The entertainment and bar staff were the best. The other staff at the resort were not very welcoming. You had to say good morning or hello otherwise they did not speak. The ..."

Reviewed on 2025/7/10

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
The price is NT$5,553 per night from Jul 17 to Jul 18
NT$5,553
NT$6,944 total
Jul 17 - Jul 18
includes taxes & fees
8.2/10 Very Good! (319 reviews)
"Property is kind of far from all the areas you probably want to see and go to but the property is nice and worth the money.You will most definitely need a car to get around but the rooms are spacious clean and nice"

Reviewed on 2025/7/10

Hilton Grand Vacations Club The Crane Barbados
Hilton Barbados Resort
Hilton Barbados Resort
4.5 out of 5
Needhams Point, Bridgetown
Fully refundableReserve now, pay when you stay
The price is NT$7,837 per night from Jul 28 to Jul 29
NT$7,837
NT$9,686 total
Jul 28 - Jul 29
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
"The property is nice and clean. They serviced your room as requested."

Reviewed on 2025/7/10

Hilton Barbados Resort
See all 3,428 properties in Cheapside
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.

Discover the most popular places to visit in Cheapside

George Washington House showing a house and heritage architecture

George Washington House

4/5(7 reviews)

Visit the same house and surroundings where the first U.S. president stayed over 250 years ago on his visit to Barbados.

George Washington House

Frequently asked questions

How much does a Cheapside vacation package cost?
You'll find cheap prices on Expedia for your Cheapside break. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Cheapside costs.
What are the cheapest months to go to Cheapside?
You can generally find lower prices and better availability in May, September and October. Take a look at our cheap Cheapside vacation packages and you could land some great off-season discounts.
How many days is enough for Cheapside?
Usually, a handful of days is enough to visit the major attractions during your Cheapside vacation. But if you'd like to have time to rest or go on day trips, consider extending your itinerary.
How to find the best Cheapside package deals?
Use Expedia's filter tool to find some tempting Cheapside package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Cheapside package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Cheapside vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored Cheapside vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Cheapside?
Enjoy amazing discounts by booking your flights early with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Cheapside adventure.
How to plan a trip to Cheapside?

  1. Pick your dates: What you plan to do in Cheapside and your preferred season will help you decide when to go.
  2. Set your budget: Consider expenses such as flights, food and transportation when working out how much to set aside for your trip to Cheapside. Then, pick a property that suits your budget, whether that's an economical option or a lavish retreat.
  3. Determine how many days away: Start by compiling a list of the activities and sights you'd like to get to in Cheapside. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to pick a Cheapside vacation package that brings all your bookings together.

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