Windy Hill Vacations from $1,171

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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.
Sea Symphony Villa

Sea Symphony Villa

3.5 out of 5
Save 100% on your flight
Price was $1,807, price is now $1,171 per person
$1,171
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
9.2/10 Wonderful! (9 reviews)
The staff was wonderful, chef made delicious Bajan meals, very accommodating and pleasant stay…will definitely be back- thank you for a relaxing stress free birthday vacation!

Reviewed on Aug 6, 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 $4,942, price is now $2,541 per person
$2,541
per person
Jan 5 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
8.8/10 Excellent! (188 reviews)
Overall felt like an upscale hotel experience more than a true all inclusive 5 star resort. The property is small but nice, the pools feel a bit too small to fully enjoy to be honest The food was great and there was a wide variety of options to choose from. The service was generally good but I would avoid the tapas bar, there were strange vibes there and poor portion sizes (yes even for tapas). The beachfront is just okay, as a strong swimmer I was able to enjoy the water, but expect some decent sized waves and not really a type of beach to just relax in the water, although the nearby Dover beach is much more pleasant (but you'll need to pay to rent chairs and umbrella there. Overall it was a good experience, but not a true 5 star experience in my opinion.

Reviewed on Oct 14, 2025

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

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

4 out of 5
Save 100% on your flight
Price was $2,995, price is now $1,684 per person
$1,684
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
8/10 Very Good! (433 reviews)
The stay was relaxing and enjoyable. The staff was helpful and friendly. Drinks could be betters

Reviewed on Oct 20, 2025

Fairmont Royal Pavilion

Fairmont Royal Pavilion

5 out of 5
Save 100% on your flight
Price was $14,161, price is now $8,333 per person
$8,333
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
9/10 Wonderful! (240 reviews)
An excellent property at the beautiful beach

Reviewed on Oct 24, 2025

The Sands Barbados All Inclusive

The Sands Barbados All Inclusive

4 out of 5
Save 100% on your flight
Price was $3,858, price is now $2,587 per person
$2,587
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
7.8/10 Good! (110 reviews)
Breakfast and was outstanding. Dinner option could be improved. The beach view was excellent. Bar service was good. The staff was very helpful and courteous. Need better fans in te room areas that doesn't hace A/C.

Reviewed on Sep 21, 2025

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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
$263 nightly
The price is $296 total per night from Oct 31 to Nov 1
$296 total
Oct 31 - Nov 1
Total with taxes and fees
8.2/10 Very Good! (1,009 reviews)
Wonderful property

Reviewed on Oct 19, 2025

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
Fully refundableReserve now, pay when you stay
$575 nightly
The price is $642 total per night from Oct 27 to Oct 28
$642 total
Oct 27 - Oct 28
Total with taxes and fees
7.6/10 Good! (516 reviews)
Amazing!!!! Loved everything!!

Reviewed on Oct 16, 2025

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
$374 nightly
The price is $420 total per night from Nov 2 to Nov 3
$420 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
we did not receive any VIP access. I didn't realize this was something we had to request!! I believe we should have received a daily food credit which was not offered! we ate at the restaurants / ice cream shop daily and received no credit or discount. We were changed for a meal on 9/18/25 when we ...

Reviewed on Sep 30, 2025

The Crane Resort
See all 3,524 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

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Frequently asked questions

How much does a Windy Hill vacation package cost?
Offering great value package deals from $1,171 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.