
Deals on vacations and trips to Windy Hill
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Windy Hill flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.

The Crane Resort
Price was $2,122, price is now $1,073 per person
$1,073
per person
Mar 8 - Mar 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
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.

Sea Breeze Beach House by Ocean Hotels - All Inclusive
Price was $3,103, price is now $1,594 per person
$1,594
per person
Mar 25 - Mar 29
found 1 day 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
Price was $5,120, price is now $2,642 per person
$2,642
per person
Mar 25 - Mar 29
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.

O2 Beach Club & Spa by Ocean Hotels - All Inclusive
Price was $4,392, price is now $2,301 per person
$2,301
per person
Mar 25 - Mar 29
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 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
Save 100% on your flight
Price was $4,703, price is now $2,666 per person
$2,666
per person
Mar 8 - Mar 13
found 1 day 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.
Top Windy Hill hotels deals

Hilton Barbados Resort
Needhams Point Bridgetown
Free Cancellation
Reserve now, pay when you stay
$505 nightly
The price is $560 total per night
$560 total
Feb 2 - Feb 3
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

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort
End of Belair Road Long Bay St. Philip
$733 nightly
The price is $816 total per night
$816 total
Jan 22 - Jan 23
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
100 Ocean Way, Silver Sands Oistins Christ Church
Free Cancellation
Reserve now, pay when you stay
$332 nightly
The price is $369 total per night
$369 total
Jan 29 - Jan 30
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

The Crane Resort
Crane Diamond Valley St. Philip
Free Cancellation
Reserve now, pay when you stay
$629 nightly
The price is $699 total per night
$699 total
Jan 30 - Jan 31
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

Sugar Bay Barbados - All Inclusive
Garrison Historic Area Hastings
$847 nightly
The price is $941 total per night
$941 total
Feb 4 - Feb 5
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

Waves Resort & Spa, Barbados, An Autograph Collection® All-Inclusive Resort
Prospect Bay Beach Prospect St. James
Free Cancellation
Reserve now, pay when you stay
$903 nightly
The price is $1,003 total per night
$1,003 total
Jan 28 - Jan 29
Total with taxes and fees
A full-service spa, 2 restaurants, and 2 outdoor pools are all featured at this all-inclusive property. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like buffet breakfast and valet parking.
Pool
Hot Tub
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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