Cheapside Holidays

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    Better together
    Save up to €185 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

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 €460 per night from 28 Jun to 29 Jun
€460
28 Jun - 29 Jun
includes taxes & fees
7.6/10 Good! (417 reviews)
"This property saved my birthday trip. Everyone was so friendly, it felt like home. I almost didn’t want to leave, and extend my stay instead. When you get there, tell Joséa that Cynthia sent you. Don’t wait book now. I will definitely be back and I’m bringing all my family members with me."

Reviewed on 23 Jun 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 €165 per night from 9 Jul to 10 Jul
€165
9 Jul - 10 Jul
includes taxes & fees
8.2/10 Very Good! (296 reviews)
"The property is beautiful and well maintained. The staff were friendly and accommodating. The Crane Beach waters were rough probably due to the windy weather. Very beautiful and I did go in but only to my knees😊 We plan to return."

Reviewed on 21 Jun 2025

Hilton Grand Vacations Club The Crane Barbados
The Crane Resort
The Crane Resort
4.5 out of 5
Crane, Diamond Valley, St. Philip
Fully refundableReserve now, pay when you stay
8.4/10 Very Good! (1,000 reviews)
"We are already planning our next stay at the crane, this is how good it is! Room: private pool which the kids loved, private elevator to the room"

Reviewed on 22 Jun 2025

Get rates
The Crane Resort
See all 3,403 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.

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.

Popular places to visit

Brownes Beach

Brownes Beach

4.5/5(29 reviews)

If a restful holiday is part of your travel plans, Brownes Beach might be the perfect place to visit during your trip to Bridgetown. Wander the area's seaside or simply enjoy one of its top-notch restaurants.

Brownes Beach
Brighton Beach featuring a beach, tropical scenes and landscape views

Brighton Beach

4.5/5(13 reviews)

One of the best-known beaches for short-term visitors, a popular spot for locals, and a must visit for rum drinkers.

Brighton Beach
Paradise Beach featuring landscape views and a sandy beach

Paradise Beach

4/5(8 reviews)

One of the most popular starting off points for serious divers. Several wrecks offer beginning to advanced depth exploration.

Paradise Beach

What to do in Cheapside

Harrison’s Cave Tram and Nature Walk Experience

Harrison’s Cave Tram and Nature Walk Experience

€87
per traveller
82% of travellers recommend
Harrison’s Cave Tram and Nature Walk Experience
Barbados- Luxury Sunset Coastline Cruise All Inclusive

Barbados- Luxury Sunset Coastline Cruise All Inclusive

€87
per adult
100% of travellers recommend
Barbados- Luxury Sunset Coastline Cruise All Inclusive
Barbados: Beach Day and Turtle Swim Experience

Barbados: Carlisle Bay Beach Day and Turtle Swim Experience

€44
per adult
Barbados: Carlisle Bay Beach Day and Turtle Swim Experience
See all activities in Cheapside
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.