Cheapside Vacations from $1,251

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

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.
The Crane Resort

The Crane Resort

4.5 out of 5
Price was $2,487, price is now $1,251 per person
$1,251
per person
Mar 5 - Mar 11
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
8.6/10 Excellent! (1,002 reviews)
Bathroom fixtures need updates. Couch cover had holes and dirty. Overall room spacious and great amenities.

Reviewed on Jan 26, 2026

O2 Beach Club & Spa by Ocean Hotels - All Inclusive

O2 Beach Club & Spa by Ocean Hotels - All Inclusive

5 out of 5
Price was $7,160, price is now $3,749 per person
$3,749
per person
Mar 5 - Mar 11
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
8.8/10 Excellent! (192 reviews)
We really enjoyed the location of the O2 resort. It is a beautiful ocean front view and very clean outside areas. The staff is very friendly, not going to go the extra mile but very friendly and do their job. I do recommend tips as the top staff will want to help out more. Housekeeping cleans but not great. Maybe like a 5/10 for housekeeping. They don’t restock all the towels or the free mini bar fridge very well. I would also recommend taking any valuables such as jewelry or cash everywhere with you. We did have $80 taken from our son’s wallet by housekeeping and our safe code was also oddly changed and we had to get maintence and we were missing $220. Otherwise everything was good. Housekeeping would be our biggest issue. Our trip was still great and we loved the Island!

Reviewed on Jan 21, 2026

Sea Breeze Beach House by Ocean Hotels - All Inclusive

Sea Breeze Beach House by Ocean Hotels - All Inclusive

4 out of 5
Price was $5,573, price is now $2,932 per person
$2,932
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Bridgetown (BGI)
8.4/10 Very Good! (367 reviews)
Staff willingness to make your stay comfortable.

Reviewed on Dec 30, 2025

Luxury Collection at Sea Breeze Beach House by Ocean Hotels

Luxury Collection at Sea Breeze Beach House by Ocean Hotels

4.5 out of 5
Price was $8,416, price is now $4,685 per person
$4,685
per person
Mar 5 - Mar 11
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
8.6/10 Excellent! (100 reviews)
Clean and amazing Staff

Reviewed on Dec 31, 2025

Concierge Collection at O2 Beach Club & Spa by Ocean Hotels

Concierge Collection at O2 Beach Club & Spa by Ocean Hotels

5 out of 5
Save 100% on your flight
Price was $6,954, price is now $4,093 per person
$4,093
per person
Apr 18 - Apr 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Bridgetown (BGI)
9/10 Wonderful! (36 reviews)
The staff was exceptionally friendly and professional. Location is great if you want peace and quiet; it’s not near too many other resorts. There are clubs nearby, outdoor which allows you to enjoy the outdoor air and environment. You have to take a taxi to go from the resort to downtown or walk maybe quarter a mile to bus transportation, which was easy to use.

Reviewed on Sep 15, 2025

Don't see what you're looking for?
See all available trips from Columbus to Cheapside
View all trips

Discover the most popular places to visit in Cheapside

Harbour Lights Carlisle Bay Beach - tropical beach on the Caribbean island of Barbados. It is a paradise destination with a white sand beach and turquoiuse sea.

Carlisle Bay

Commune with nature and explore the great outdoors at Carlisle Bay during your travels in Bridgetown. Amble around this family-friendly area's beautiful beaches and enjoy its top-notch restaurants.

Carlisle Bay
Paradise Beach which includes a sandy beach and landscape views

Paradise Beach

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

Paradise Beach
Panorama of a beautiful sunny day at Bayshore / Pebbles Beach (Carlisle Bay) near Bridgetown Barbados

Pebbles Beach

If a restful vacation is part of your travel plans, Pebbles Beach might be the perfect place to seek out during your trip to Bridgetown. Wander the area's seaside or simply enjoy one of its lively bars.

Pebbles Beach

What to do in Cheapside

Barbados -Luxury Cruise with Lunch and Open Bar

Barbados -Luxury Cruise with Lunch and Open Bar By Oceanluxx

$130
per adult
100% of travellers recommend
Barbados -Luxury Cruise with Lunch and Open Bar By Oceanluxx
Bathsheba, Barbados

Barbados Small-Group Monkey Feeding Experience

$75
per adult
100% of travellers recommend
Barbados Small-Group Monkey Feeding Experience
Group tours

Mount Gay Signature Rum Tasting Experience

$36
per adult
100% of travellers recommend
Mount Gay Signature Rum Tasting Experience
See all activities in Cheapside

Cheapside Hotel Deals

Hilton Barbados Resort

Hilton Barbados Resort

4.5 out of 5
Needhams Point Bridgetown
Fully refundableReserve now, pay when you stay
$547 nightly
The price is $606 total per night from Feb 3 to Feb 4
$606 total
Feb 3 - Feb 4
Total with taxes and fees
8.2/10 Very Good! (1,006 reviews)
Everything was amazing! The staff were helpful and friendly. The space itself was beautiful and made for a perfect relaxing getaway. There is nothing I would change about the Hilton Barbados!

Reviewed on Jan 23, 2026

Hilton Barbados Resort
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
$733 nightly
The price is $816 total per night from Jan 27 to Jan 28
$816 total
Jan 27 - Jan 28
Total with taxes and fees
7.6/10 Good! (568 reviews)
The swim up bar was the best good music and entertainment food could been better

Reviewed on Jan 4, 2026

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort
The Crane Resort

The Crane Resort

4.5 out of 5
Crane Diamond Valley St. Philip
Fully refundableReserve now, pay when you stay
$629 nightly
The price is $699 total per night from Feb 6 to Feb 7
$699 total
Feb 6 - Feb 7
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
Room was decent, shower was tiny. Nice kitchenette, lovely balcony. Beach is small and covered with seaweed. Pools are decent. Overall, the resort is a little tired and not the best beach on the island. Service was ok. Not brilliant, ok.

Reviewed on Jan 24, 2026

The Crane Resort
See all 3,447 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.

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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Cheapside vacation package cost?
You'll find cheap prices from $1,251 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.