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Windy Hill Vacation Packages

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A coastal landscape with clear blue ocean, green hills, and palm trees.

Windy Hill
St. Andrew
Barbados
Caribbean
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Windy Hill Flight + Hotel Packages

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

East Resort

3.5 out of 5

Price was $1,437, price is now $989 per person

$989

per person

Nov 23 - Nov 27

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Bridgetown (BGI)

Stay at this villa in Whitehaven. Enjoy free WiFi, free parking, and private pools. Popular attractions Crane Beach and Ragged Point Lighthouse are located nearby.

Luxury Collection at Sea Breeze Beach House by Ocean Hotels

4.5 out of 5

Save 100% on your flight

Price was $6,528, price is now $4,037 per person

$4,037

per person

Dec 12 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Charleston (CHS) to Bridgetown (BGI)

Book a stay at this luxury resort in Maxwell. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Dover Beach and Miami Beach are located nearby.

South Point Hotel

4.5 out of 5

Save 100% on your flight

Price was $3,277, price is now $2,085 per person

$2,085

per person

Dec 12 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Charleston (CHS) to Bridgetown (BGI)

Book a stay at this luxury hotel in Oistins. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Miami Beach and Dover Beach are located nearby.

Simple and comfortable.

Reviewed on Oct 4, 2026

Concierge Collection at O2 Beach Club & Spa by Ocean Hotels

5 out of 5

Save 100% on your flight

Price was $7,105, price is now $4,551 per person

$4,551

per person

Dec 12 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Charleston (CHS) to Bridgetown (BGI)

Book a stay at this luxury hotel in St. Lawrence Gap. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Dover Beach and Miami Beach are located nearby.

The Soco Hotel - Adults Only

4 out of 5

Save 100% on your flight

Price was $3,562, price is now $2,335 per person

$2,335

per person

Dec 12 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Charleston (CHS) to Bridgetown (BGI)

Book a stay at this all-inclusive hotel in Hastings. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Rockley Beach and Carlisle Bay are located nearby.

ECO Lifestyle & Lodge

3 out of 5

Save 100% on your flight

Price was $2,235, price is now $1,486 per person

$1,486

per person

Dec 12 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Charleston (CHS) to Bridgetown (BGI)

Book a stay at this boutique hotel in Bathsheba. Enjoy free breakfast, free parking, and 3 hot tubs. Our guests praise the room service in our reviews. Popular attractions Tent Bay and Bathsheba Beach are located nearby.

Enjoyed every bit of my stay at Ecolifestyle lodge. WiIshed we stayed a little longer. Staff was extremely accommodating. It was peaceful and safe. The views from our room (soup bowl) was breath taking. And listening to the ocean waves and breeze in the morning was everything. If you like low key and chill vibes. This is the place to stay.

Reviewed on Jul 1, 2026

The Crane Resort

4.5 out of 5

Save 100% on your flight

Price was $2,269, price is now $1,536 per person

$1,536

per person

Dec 12 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Charleston (CHS) to Bridgetown (BGI)

Book a stay at this luxury resort in Diamond Valley. Enjoy free WiFi, free parking, and 5 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Crane Beach and Foul Bay Beach are located nearby.

Seabliss Villa

3 out of 5

Price was $1,949, price is now $1,323 per person

$1,323

per person

Dec 12 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Charleston (CHS) to Bridgetown (BGI)

Book a stay at this beach villa in Fryers Well. Enjoy private pools, private hot tubs, and room service. Popular attractions Mullins Beach and Port St. Charles Marina are located nearby.

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