Windy Hill Vacations from $1,249

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 Windy Hill Vacation

Reserve a Windy Hill vacation package that has only the things you need and nothing you don't. Great for coastal beaches, watersports and nature, think about staying in the neighborhood of Foul Bay. Barbados Wildlife Reserve, St. Andrews Anglican Church and Morgan Lewis Sugar Mill are just some of the many sights worth exploring during your trip to Windy Hill. Stop dreaming and start traveling. Check out the wide range of options on Expedia today and finally put your Windy Hill vacation plans into action!

The Latest Windy Hill 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 $1,249 per person
$1,249
per person
Mar 8 - Mar 14
found 1 day 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

Concierge Collection at O2 Beach Club & Spa by Ocean Hotels

Concierge Collection at O2 Beach Club & Spa by Ocean Hotels

5 out of 5
Price was $7,501, price is now $3,834 per person
$3,834
per person
Mar 8 - Mar 14
found 1 day ago
Roundtrip non-stop 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

O2 Beach Club & Spa by Ocean Hotels - All Inclusive

O2 Beach Club & Spa by Ocean Hotels - All Inclusive

5 out of 5
Price was $7,062, price is now $3,749 per person
$3,749
per person
Mar 8 - Mar 14
found 1 day 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 $3,089, price is now $1,685 per person
$1,685
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip non-stop 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 $6,512, price is now $3,660 per person
$3,660
per person
Mar 21 - Mar 28
found 1 day 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

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

Windy Hill Hotel Deals

Hilton Barbados Resort

Hilton Barbados Resort

4.5 out of 5
Needhams Point Bridgetown
Fully refundableReserve now, pay when you stay
$549 nightly
The price is $608 total per night from Feb 3 to Feb 4
$608 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 28 to Jan 29
$816 total
Jan 28 - Jan 29
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 4 to Feb 5
$699 total
Feb 4 - Feb 5
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 3,430 properties in Windy Hill
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 Windy Hill Vacation Packages

Windy Hill Essential Information

Language
English
Currency
Barbadian dollars
Closest Airport
Grantley Adams Intl. Airport (BGI)
Max Temp Winter
80ºF
Max Temp Summer
80ºF
Top Sights
Barbados Wildlife Reserve, Farley Hill National Park and St. Andrews Anglican Church

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 Windy Hill vacation package cost?
Offering great value package deals from $1,249 on Expedia, you'll be thrilled with how little a vacation to Windy Hill costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Windy Hill?
You can usually find lower prices and greater availability in September, November and December. Explore our cheap Windy Hill vacation packages and you could land some excellent off-season deals.
How many days is enough for Windy Hill?
With a well-organized travel plan, you can easily tick off the top Windy Hill attractions in a few days. But if you prefer to discover lesser-known spots or take day trips, think about booking your Windy Hill vacation for longer.
How to find the best Windy Hill package deals?
Begin your search for a Windy Hill package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Windy Hill package deal straight away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Windy Hill escape underway.
Is it cheaper to book a Windy Hill vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging hotels and flights individually. Better still, you can tailor your Windy Hill escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Windy Hill?
Enjoy amazing discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Windy Hill getaway.
How to plan a trip to Windy Hill?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Windy Hill.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and food to airfares and activities. Your hotel will probably be the biggest expense during your trip to Windy Hill.
  3. Explore Windy Hill using Expedia's trip planning tool: Gain insights into the top attractions and best hotels for your trip to Windy Hill. You can also save your favorite locations, collaborate with friends and family and manage all your plans in one place.
  4. Decide how long to go for: Now that you're up to speed on Windy Hill, you can figure out the ideal length of your break. Create a rough plan and give yourself enough time to cover everything you want to see.
  5. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customized Windy Hill vacation package.
  6. Add on excursions and experiences: Read our dedicated travel guide to find some incredible things to do in Windy Hill. Book tickets or make reservations as soon as you can to save time and avoid the hassle of trying to find activities when you arrive.

Does Expedia offer Book Now, Pay Later Windy Hill vacation packages?
If you're like us, you love going away but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Windy Hill trip across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.