Deals on vacations and trips to Windy Hill

Save when you book Windy Hill package deals

Choose two or more items and save on your trip:

Windy Hill flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
South Point Hotel

South Point Hotel

4.5 out of 5
Green Garden
Save 100% on your flight
Price was $2,092, price is now $1,158 per person
$1,158
per person
Feb 2 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Families will appreciate the convenience store and in-room childcare. Guests will appreciate free perks like free self parking and WiFi in public areas.
O2 Beach Club & Spa by Ocean Hotels - All Inclusive

O2 Beach Club & Spa by Ocean Hotels - All Inclusive

5 out of 5
Price was $4,548, price is now $2,093 per person
$2,093
per person
Mar 2 - Mar 6
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
A full-service spa, 4 restaurants, and 3 outdoor pools are all featured at this all-inclusive hotel. Relax with sun loungers and beach umbrellas, and enjoy a drink at one of the 2 beachside bars. Families will appreciate in-room childcare, along with kayaking.
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 $3,794, price is now $1,887 per person
$1,887
per person
Mar 2 - Mar 6
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
A full-service spa, 5 restaurants, and 3 outdoor pools are all featured at this luxury resort. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Relax with a drink at one of the 4 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.
Sea Breeze Beach House by Ocean Hotels - All Inclusive

Sea Breeze Beach House by Ocean Hotels - All Inclusive

4 out of 5
Price was $3,628, price is now $1,811 per person
$1,811
per person
Mar 2 - Mar 6
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
This all-inclusive property features 6 restaurants, 3 outdoor pools, and 2 hot tubs. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Bring the family and enjoy the free kid's club, arcade/game room, and kid-friendly dining.
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 $8,710, price is now $4,410 per person
$4,410
per person
Feb 2 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
A full-service spa, 4 restaurants, and 3 outdoor pools are all featured at this all-inclusive hotel. Relax with a drink at one of the 6 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. A coffee shop, dry cleaning, and concierge services are also on offer.

Top Windy Hill hotels deals

Santosha Barbados

Santosha Barbados

3.5 out of 5
Windy Hill Windy Hill St. Andrew
Get rates
This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the express check-in and airport shuttle. There's an outdoor pool on site, and laundry facilities and concierge services are also offered.
Pool
Kitchen
The Crane Resort

The Crane Resort

4.5 out of 5
Crane Diamond Valley St. Philip
Free Cancellation
Reserve now, pay when you stay
$581 nightly
The price is $651 total per night
$651 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
A full-service spa, 5 restaurants, and 5 outdoor pools are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Relax with a drink at one of the 2 bars/lounges and enjoy perks like free self parking.
Pool
Spa
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
Free Cancellation
Reserve now, pay when you stay
$733 nightly
The price is $816 total per night
$816 total
Jan 3 - Jan 4, 2026
Total with taxes and fees
This property features 3 restaurants, 6 outdoor pools, and a gym. Take the free beach shuttle and relax with sun loungers and beach umbrellas. Unwind with a drink at one of the 3 bars/lounges and enjoy free perks like free self parking and a beach shuttle.
Pool
All inclusive
South Point Hotel

South Point Hotel

4.5 out of 5
100 Ocean Way, Silver Sands Oistins Christ Church
Free Cancellation
Reserve now, pay when you stay
$269 nightly
The price is $301 total per night
$301 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Families will appreciate the convenience store and in-room childcare. Guests will appreciate free perks like free self parking and WiFi in public areas.
Pool
Spa
Hilton Barbados Resort

Hilton Barbados Resort

4.5 out of 5
Needhams Point Bridgetown
Free Cancellation
Reserve now, pay when you stay
$538 nightly
The price is $596 total per night
$596 total
Jan 18 - Jan 19, 2026
Total with taxes and fees
A full-service spa, 3 restaurants, and an outdoor pool are all featured at this smoke-free resort. Relax with free beach cabanas, sun loungers, and beach umbrellas. Families will appreciate the children's pool, kid-friendly dining, and in-room childcare.
Pool
Hot Tub
Sugar Bay Barbados - All Inclusive

Sugar Bay Barbados - All Inclusive

4 out of 5
Garrison Historic Area Hastings
$788 nightly
The price is $882 total per night
$882 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
A full-service spa, 4 restaurants, and 2 outdoor pools are all featured at this all-inclusive property. There's fun for all ages with a free kid's club and a playground, and babysitting is an added bonus. Relax with a drink at one of the 5 bars/lounges and enjoy free perks like buffet breakfast and free self parking.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Windy Hill
View all properties
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.

Frequently asked questions

How much are vacation packages to Windy Hill?
$1,158 is all you'll need for a wonderful vacation in Windy Hill. Bundle your flights and hotel into a vacation package with Travelocity and watch the savings add up. With prices as good as these, it's never been easier to travel!
How long should my Windy Hill vacation be?
Many travelers book a hotel for 7 nights in Windy Hill. But that doesn't necessarily mean you have to follow suit. How long you stay all depends on how much you want to do on your vacation. If you want to get familiar with every corner of this wonderful location, book another night or so (or even longer!).
Where can I get the best vacation package deals for Windy Hill?
Check out Travelocity. With access to 400 airlines and an impressive 1,000,000 hotels around the world, creating the ultimate Windy Hill package deal couldn't be simpler.
Why should I book my Windy Hill vacation package via Travelocity?
Nothing beats the feeling of knowing you've just bagged the best price in town — that's our Price Match Guarantee. Add to that our impressive range of magical destinations and 24/7 team of customer service professionals and you've got the blueprint for an unforgettable vacation.
Can I save on my Windy Hill car rental if I book it with a hotel or flight?
You certainly can with our Windy Hill vacation packages. With one of these, there are lots of ways to make your travel budget go further. Combine any two or more car, flight, hotel and tour bookings and watch the savings start to add up. With your own ride, all the popular attractions in and around Windy Hill are an unforgettable road trip away.
Which airport is best for Windy Hill?
Grantley Adams Intl. Airport (BGI), the main terminal in Windy Hill, is where you'll step off the plane. It's 12 mi south of the center of town.
Where should I stay when visiting Windy Hill?
The Santosha Barbados is the first choice of many visitors. Book now before it's too late.

Photos of local treasures

Browse Windy Hill vacation photos for more inspiration