Cheapside Vacations from $697

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Your Cheapside Vacation

Reserve a Cheapside vacation package and get set to experience everything this city has to offer. Consider staying in the neighborhood of Foul Bay, which is great for coastal beaches, watersports and nature. Any trip to Cheapside needs a well-planned itinerary. Fill yours with famous sights like Brownes Beach, Kensington Oval and Barbados Parliament Buildings. Stop dreaming and start traveling. Browse the broad range of options on Expedia today and finally put your Cheapside vacation plans in motion!

The Latest Cheapside vacation packages

Price found within the past 48 hours. Click for updated prices.
Sunbay Hotel
O2 Beach Club & Spa by Ocean Hotels
Luxury Collection at Sea Breeze Beach House by Ocean Hotels
Concierge Collection at O2 Beach Club & Spa by Ocean Hotels
The Sands Barbados All Inclusive
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Discover the most popular places to visit in Cheapside

What to do in Cheapside

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
$479 nightly
The price is $537 total per night from Jul 12 to Jul 13
$537 total
Jul 12 - Jul 13
Total includes taxes and 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 Jul 10, 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
$210 nightly
The price is $238 total per night from Jul 17 to Jul 18
$238 total
Jul 17 - Jul 18
Total includes taxes and fees
8.2/10 Very Good! (317 reviews)
Bae/Staycation
"The hotel and room was AMAZING!!! The only complaints I have are to at the pool area is not super private. We had children above us on the balcony and neighbors to the left of us… This made the area not seem so “private”. Also, there were a few bugs that came in the kitchen when we cooked. The last ..."

Reviewed on Jul 7, 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
$263 nightly
The price is $296 total per night from Aug 5 to Aug 6
$296 total
Aug 5 - Aug 6
Total includes taxes and fees
8.2/10 Very Good! (1,007 reviews)
"The property is nice and clean. They serviced your room as requested."

Reviewed on Jul 10, 2025

Hilton Barbados Resort
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.

Find the Best Cheapside Vacation Packages

Cheapside Essential Information

Language
English
Currency
Barbadian dollars
Closest Airport
Grantley Adams Intl. Airport (BGI)
Top Sights
Brownes Beach, Brighton Beach and Paradise Beach

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Frequently asked questions

How much does a Cheapside vacation package cost?
You'll find cheap prices from $697 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?
If you're looking to snag a cheap Cheapside vacation package, consider planning a trip in October, November and December. You're likely to find better prices on hotels and airfares during these quieter months --- ideal for a budget-friendly getaway.
How many days is enough for Cheapside?
Generally, a handful of days is enough to see the main sights during your Cheapside vacation. But if you prefer to have time to unwind or take day tours, think about 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 the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Cheapside.
  2. Work out your budget: Ensure you have enough money to pay for everything from dining out and transportation to flights and activities. Your hotel will probably be the largest expense during your trip to Cheapside.
  3. Discover Cheapside using our trip planning tool: Gain insights into the leading attractions and best stays for your trip to Cheapside. You can also save your favorite locations, collaborate with family and friends and manage all your plans in one place.
  4. Work out your trip length: Think about how long you want to spend discovering Cheapside. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
  5. Combine 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.
  6. Book activities and experiences ahead of time: Whether it's entrance to a major attraction or a day trip in nature, you won't have to worry about missing out on the best Cheapside has to offer. Find all the incredible things to do in Cheapside with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Cheapside vacation packages?
Your Cheapside trip is meant to be an escape from your busy life, not a source of money worries. So to allow you more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.