Windy Hill Vacations from $1,255

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

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

4 out of 5
Price was $2,702, price is now $1,255 per person
$1,255
per person
Nov 12 - Nov 17
found 1 day ago
Roundtrip flight included
New York (JFK) to Bridgetown (BGI)
8/10 Very Good! (414 reviews)
I had read a lot of reviews about this property and was a little apprehensive. But rest assured staff were great, decor and rooms are a little older but that is caribbean style and what the islands were about. food was tasty and freshly made with some good choices, drinks were heavily pourer and some great cocktails. overall great experience, i had a car so i would suggest you rent one as it is needed. i will be back again at the end of the year

Reviewed on Aug 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 $8,809, price is now $3,797 per person
$3,797
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Bridgetown (BGI)
8.8/10 Excellent! (178 reviews)
The room was really old and smelt of mold. It took more than 24 hours to sort it out. I was downgraded to a smaller and newer room, but had to pay extra. The rest of the staff by pool and resteraunts were really helpful and kind.

Reviewed on Aug 14, 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
Price was $6,498, price is now $2,958 per person
$2,958
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Bridgetown (BGI)
8.8/10 Excellent! (35 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
Price was $4,446, price is now $2,367 per person
$2,367
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Bridgetown (BGI)
8.6/10 Excellent! (89 reviews)
Enjoyed our time. Staff was professional and courteous. Rated property a 3 as I felt it is a 3 Star resort. Beautiful beach with plenty of beach activities.

Reviewed on Aug 24, 2025

Sea Breeze Beach House by Ocean Hotels - All Inclusive

Sea Breeze Beach House by Ocean Hotels - All Inclusive

4 out of 5
Price was $3,990, price is now $2,126 per person
$2,126
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Bridgetown (BGI)
8.4/10 Very Good! (347 reviews)
This hotel is one if not the best in Barbados. The staff are there to help at a moments notice and our ambassador Fabian was outstanding. If we needed anything he was right there to help even on his day off. This was auch a great experience, i would definitely recommend Sea Breeze to everyone. We will definitely be going back

Reviewed on Aug 26, 2025

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Windy Hill Hotel Deals

Santosha Barbados

Santosha Barbados

3.5 out of 5
Windy Hill, Windy Hill, St. Andrew
9.2/10 Wonderful! (144 reviews)
"Nice clean quietrelaxing accommodations"

Reviewed on Apr 24, 2025

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Santosha 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 Sep 23 to Sep 24
$296 total
Sep 23 - Sep 24
Total with taxes and fees
8.2/10 Very Good! (1,007 reviews)
"Very helpful and pleasant staff"

Reviewed on Aug 26, 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
$453 nightly
The price is $508 total per night from Aug 29 to Aug 30
$508 total
Aug 29 - Aug 30
Total with taxes and fees
7.6/10 Good! (476 reviews)
"Pros: Amazing hotel, room cleanliness and spacious, food delicious, staff extremely helpful and nice. Cons: Only one real restaurant to pick from outside of the buffet, transportation is costly to get around, hotel is fairly far from the attractions."

Reviewed on Aug 20, 2025

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort
See all 3,468 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.

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Frequently asked questions

How much does a Windy Hill vacation package cost?
Offering great value package deals from $1,255 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.