Deals on vacations and trips to Cheapside
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Cheapside flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club The Crane Barbados
Save 100% on your flight
Price was $3,226, price is now $1,832 per person
$1,832
per person
Mar 8 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Bridgetown (BGI)
A full-service spa, 5 restaurants, and 2 outdoor tennis courts are all featured at this luxury resort. Enjoy the outdoor pool and perks like free self parking and free WiFi. You'll appreciate the gym, bar/lounge, and snack bar/deli.
Concierge Collection at O2 Beach Club & Spa by Ocean Hotels
Price was $7,460, price is now $3,312 per person
$3,312
per person
Mar 8 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $7,199, price is now $3,230 per person
$3,230
per person
Mar 8 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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
Price was $5,615, price is now $2,732 per person
$2,732
per person
Mar 8 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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
Price was $4,136, price is now $2,098 per person
$2,098
per person
Mar 8 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Top Cheapside hotels deals
The Crane Resort
Crane Diamond Valley St. Philip
Free Cancellation
Reserve now, pay when you stay
$587 nightly
The price is $657 total per night
$657 total
Jan 4 - Jan 5, 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
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
Hilton Barbados Resort
Needhams Point Bridgetown
$510 nightly
The price is $566 total per night
$566 total
Jan 21 - Jan 22, 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
South Point Hotel
100 Ocean Way, Silver Sands Oistins Christ Church
Free Cancellation
Reserve now, pay when you stay
$283 nightly
The price is $316 total per night
$316 total
Jan 6 - Jan 7, 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
Sugar Bay Barbados - All Inclusive
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
Accra Beach Hotel & Spa
Rockley Rockley Christ Church
Free Cancellation
Reserve now, pay when you stay
A full-service spa, 3 restaurants, and 2 outdoor pools are all featured at this smoke-free resort. Enjoy beachfront dining and relax with free beach cabanas and sun loungers. Relax with a drink at one of the 3 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.
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.
Popular places to visit
Carlisle Bay
4.5/5(277 reviews)
Commune with nature and explore the great outdoors at Carlisle Bay during your travels in Bridgetown. Amble around this family-friendly area's beautiful beaches and enjoy its top-notch restaurants.
Brownes Beach
4.5/5(126 reviews)
If a restful vacation is part of your travel plans, Brownes Beach might be the perfect place to seek out during your trip to Bridgetown. Wander the area's seaside or simply enjoy one of its top-notch restaurants.
Brighton Beach
4.5/5(47 reviews)
Why not spend a carefree afternoon at Brighton Beach during your travels in Black Rock?
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