Cheapside Vacations

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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 ₩665,219 per night from Jul 17 to Jul 18
₩665,219
₩745,102 total
Jul 17 - Jul 18
includes taxes & fees
7.6/10 Good! (440 reviews)
"Excellent customer service, dining and check in were all very professional and cordial. We enjoyed our stay and would definitely visit again."

Reviewed on Jul 13, 2025

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 ₩243,060 per night from Aug 12 to Aug 13
₩243,060
₩305,033 total
Aug 12 - Aug 13
includes taxes & fees
8.2/10 Very Good! (322 reviews)
"This property (much like the rest if Barbados) is beautiful and safe!!! The staff were amazing, very accommodating, and extremely nice! Not a lot of food options close by, but the resort has a few places to choose from. However, the food available at the resort wasn't to my liking. Do yourself a ..."

Reviewed on Jul 15, 2025

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 ₩349,637 per night from Aug 5 to Aug 6
₩349,637
₩432,925 total
Aug 5 - Aug 6
includes taxes & fees
8.2/10 Very Good! (1,010 reviews)
"It's a Hilton hotel so there is the usual level of Hilton standard but the little extras are missing. No shower caps, razors etc which are usually provided. And when we got our bill, room cleaning was charged as an extra"

Reviewed on Jul 13, 2025

Hilton Barbados Resort
See all 3,446 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

The capital building clock tower.

Barbados Parliament Buildings

4/5(117 reviews)

Barbados Parliament Buildings is just one of the places to see in Bridgetown, so why not enjoy the other things to explore during your travels? Discover the area's beautiful sunsets and seafood restaurants.

Barbados Parliament Buildings

Barbados Museum & Historical Society

4/5(5 reviews)

You can spend time studying the exhibits at Barbados Museum & Historical Society during your travels in Bridgetown. Wander the area's beautiful beaches or simply enjoy one of its seafood restaurants.

Barbados Museum & Historical Society

Bethel Methodist Church

Find out about the history of Henrys when you spend time at Bethel Methodist Church. Wander the area's beautiful beaches or simply enjoy one of its seafood restaurants.

Bethel Methodist Church

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.