Cheapside Vacation Packages

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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!

Top Cheapside Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Club, Barbados Resort & Spa Adults Only - All Inclusive

The Club, Barbados Resort & Spa Adults Only - All Inclusive

4 out of 5
per person
Sep 9 - Sep 14
found 13 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Bridgetown (BGI)
8/10 Very Good! (392 reviews)
Barbados BLISS! This luxurious, elegant and charming resort is spectacular. Be sure to visit Sharad at water sports for the most excellent nautical adventures. The entire staff is so warm, welcoming and lovely. General Manager Caroline is very caring and goes above and beyond to provide the top guest experience. I’ve been to 29 countries and I highly recommend The Club Barbados. From stunning ocean views to delicious meals and nonstop entertainment - be sure to book today. Extra special thanks to Sherry at Sunset Restaurant for being so FABULOUS.

Reviewed on Jul. 27, 2025

O2 Beach Club & Spa by Ocean Hotels

O2 Beach Club & Spa by Ocean Hotels

5 out of 5
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Bridgetown (BGI)
9/10 Wonderful! (167 reviews)
Property had limited dining, no entertainment, room service was not good. Staff were unwelcoming! Will never go here again because it’s not setup like a real all inclusive as well as not inviting from the locals. Should be advertised more as a hotel and for the price could have been a much better experience!

Reviewed on Jul. 29, 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
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Bridgetown (BGI)
9/10 Wonderful! (33 reviews)
Oceanfront room decor was great! Wristband double as room key. Turndown service inconsistent & liquor in room could be tailored to guess preference. Beach should be clean more frequently. Needs entertainment. Snacks are readily available. Ice cream shop would've been nice.

Reviewed on Jul. 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
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Bridgetown (BGI)
8.6/10 Excellent! (86 reviews)
Room wasn’t ready until 4:00 pm, and the electronic doors were defective couple times, leave us unable to access to our room

Reviewed on Jul. 17, 2025

The Sands Barbados All Inclusive

The Sands Barbados All Inclusive

4 out of 5
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Bridgetown (BGI)
8/10 Very Good! (98 reviews)
My stay at The Sands Barbados All Inclusive was very nice! I needed a quick weekend escape and this spot was perfect. The location was ideal — just a short walk to St. Lawrence Gap, with easy access to the Friday night fish fry and even a cozy lounge nearby. The food was delicious, the drinks were solid, and there was plenty of seating on the beach. Everyone was so friendly, which made the experience even better. Big kudos to Kemar, one of the standout staff members. He was absolutely great! I’ll definitely be back.

Reviewed on Jul. 5, 2025

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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 CA $612 per night from Aug 8 to Aug 9
CA $612
CA $692 total
Aug 8 - Aug 9
includes taxes & fees
7.6/10 Good! (454 reviews)
"Thank yo for the kind stay"

Reviewed on Jul. 22, 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 CA $386 per night from Aug 21 to Aug 22
CA $386
CA $476 total
Aug 21 - Aug 22
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 Jul. 27, 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 CA $235 per night from Aug 31 to Sep 1
CA $235
CA $296 total
Aug 31 - Sep 1
includes taxes & fees
8.2/10 Very Good! (343 reviews)
"Enjoyed it a lot!"

Reviewed on Jul. 28, 2025

Hilton Grand Vacations Club The Crane Barbados
See all 3,452 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
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Discover the most popular places to visit in Cheapside

Brownes Beach

Brownes Beach

4.5/5(49 reviews)

If a restful vacation is part of your travel plans, Brownes 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.

Brownes Beach
Brighton Beach which includes a sandy beach, landscape views and tropical scenes

Brighton Beach

4.5/5(20 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 a sandy beach and landscape views

Paradise Beach

4/5(20 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

CA $137
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

CA $137
per adult
100% of travellers recommend
Barbados- Luxury Sunset Coastline Cruise All Inclusive
Barbados -Luxury Cruise with Lunch and Open Bar

Barbados -Luxury Cruise with Lunch and Open Bar

CA $171
per adult
100% of travellers recommend
Barbados -Luxury Cruise with Lunch and Open Bar
See all activities in Cheapside

Frequently asked questions

How much does a Cheapside vacation package cost?
You can snap up a vacation package to this popular destination from CA $1,742 on Expedia. But how much your vacation to Cheapside costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Cheapside?
If you're looking to score a cheap Cheapside vacation package, consider visiting in May, September and October. You'll generally find lower rates on hotels and airfares during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Cheapside?
With around 2 days, you'll have enough time to experience popular neighbourhoods like Garrison Historic Area and Brittons Hill during your Cheapside vacation. Make sure to also add Baxter's Road and Brownes Beach to your sightseeing list. Searching for more adventures? Consider exploring outside of Cheapside on day trips and tours.
How to find the best Cheapside package deals?
Begin your search for a Cheapside package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Cheapside package deal straight away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Cheapside adventure off to a flying start.
Is it cheaper to book a Cheapside vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and accommodations individually. Better still, you can personalize your Cheapside escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Cheapside?
If you've got your Cheapside vacation dates confirmed, book as early as you can to snap up some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Cheapside?

  1. Choose when to travel: Check your calendar and get your bags packed. Your preferred season and the activities on offer will also help you decide when to vacation in Cheapside.
  2. Set your budget: Consider expenses like food, flights and transportation when working out how much to set aside for your trip to Cheapside. Then, select a hotel that matches your budget, whether that's an affordable stay or a high-end retreat.
  3. Work out your trip length: Think about how long you'd like to spend discovering Cheapside. Plan your itinerary so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a tailored Cheapside vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.