Cheapside Holidays

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Top hotels in Cheapside

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 12.568.900 ₫ per night from 2 Aug to 3 Aug
12.568.900 ₫
14.078.240 ₫ total
2 Aug - 3 Aug
includes taxes & fees
7.6/10 Good! (452 reviews)
"Thank yo for the kind stay"

Reviewed on 22 Jul 2025

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort
Hilton Barbados Resort

Hilton Barbados Resort

4.5 out of 5
Needhams Point, Bridgetown
Fully refundableReserve now, pay when you stay
The price is 7.313.985 ₫ per night from 21 Aug to 22 Aug
7.313.985 ₫
9.029.232 ₫ total
21 Aug - 22 Aug
includes taxes & fees
8.2/10 Very Good! (1,015 reviews)
"Perfect location! The beach was beautiful but if there is low tides, you can walk over to pebble beach in Calise Bay. Great for a solo traveler"

Reviewed on 27 Jul 2025

Hilton Barbados 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 4.459.172 ₫ per night from 31 Aug to 1 Sept
4.459.172 ₫
5.603.456 ₫ total
31 Aug - 1 Sept
includes taxes & fees
8.2/10 Very Good! (344 reviews)
"Nice resort with the best rum punch on the island"

Reviewed on 29 Jul 2025

Hilton Grand Vacations Club The Crane Barbados
See all 3,441 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.

Popular places to visit

Barbados Parliament Buildings

Barbados Parliament Buildings

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
Garrison Savannah

Garrison Savannah

Catch an event at Garrison Savannah and enjoy other activities in Bridgetown such as surfing.Wander the beautiful beaches and seaside in the area.

Garrison Savannah
George Washington House featuring heritage architecture and a house

George Washington House

Find out about the history of Bridgetown when you take a trip to George Washington House. Stroll along the beautiful beaches or discover the area's beautiful sunsets.

George Washington House

Frequently asked questions

How much does a Cheapside holiday 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 holiday 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 holiday 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 holiday. 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 holiday package as soon as possible.
Is it cheaper to book a Cheapside holiday as a package?
Expedia holiday 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 holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday 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 holiday package that brings all your bookings together.