Windy Hill Vacations from $818

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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.
Seacruise Villa

Seacruise Villa

3.5 out of 5
Save 100% on your flight
Price was $1,356, price is now $818 per person
$818
per person
Jan 5 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
9.6/10 Exceptional! (5 reviews)
Seabliss Villa

Seabliss Villa

3 out of 5
Save 100% on your flight
Price was $2,061, price is now $1,099 per person
$1,099
per person
Jan 31 - Feb 7
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Bridgetown (BGI)
8.8/10 Excellent! (8 reviews)
Dorothy and Mel were absolutely wonderful! Apon arrival we were greeted with ice cold wash cloths, beers, water, 6 eggs, butter, bread and waters! We onlybstayed one night but the communication was super speedy and we had everything we needed!

Reviewed on Jun 21, 2025

O2 Beach Club & Spa by Ocean Hotels - All Inclusive

O2 Beach Club & Spa by Ocean Hotels - All Inclusive

5 out of 5
Save 100% on your flight
Price was $4,616, price is now $2,547 per person
$2,547
per person
Feb 16 - Feb 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Bridgetown (BGI)
8.8/10 Excellent! (192 reviews)
Very beautiful resort with really good food. The resort is actually impeccably clean. The rooms are gorgeous. The staff was extremely attentive. Just be careful when booking. I booked for 2 and noticed day before departure that the booking had somehow changed to a booking for 1 person, but at the same price for two! It was a little horrific as I had to pay considerably more upon arrival! Significantly more. Now I have a small claims court date to contend with. Very unfortunate. But the resort was a good one. I’ve been to many… it’s up there.

Reviewed on Oct 25, 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 $5,148, price is now $3,117 per person
$3,117
per person
Feb 11 - Feb 15
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

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 $3,835, price is now $2,352 per person
$2,352
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
8.6/10 Excellent! (100 reviews)
Staff was absolutely amazing… great job team

Reviewed on Oct 28, 2025

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Windy Hill Hotel Deals

The Crane Resort

The Crane Resort

4.5 out of 5
Crane Diamond Valley St. Philip
Fully refundableReserve now, pay when you stay
$480 nightly
The price is $536 total per night from Dec 23 to Dec 24
$536 total
Dec 23 - Dec 24
Total with taxes and fees
8.4/10 Very Good! (1,003 reviews)
The Crane Resort has everything needed for a relaxed stay in one location. Our Junior Suite with partial ocean views was smaller than expected. The bedroom and wardrobe space was small. There was no space to store luggage, except in the living/dining area, which then reduced the available space there. ...

Reviewed on Nov 24, 2025

The Crane Resort
Hilton Barbados Resort

Hilton Barbados Resort

4.5 out of 5
Needhams Point Bridgetown
Fully refundableReserve now, pay when you stay
$363 nightly
The price is $405 total per night from Dec 15 to Dec 16
$405 total
Dec 15 - Dec 16
Total with taxes and fees
8.2/10 Very Good! (1,008 reviews)
Bathroom light was broken

Reviewed on Nov 25, 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
$670 nightly
The price is $747 total per night from Nov 27 to Nov 28
$747 total
Nov 27 - Nov 28
Total with taxes and fees
7.6/10 Good! (538 reviews)
Amazing resort and staff!!!!

Reviewed on Nov 21, 2025

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort
See all 3,702 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 $818 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.