Deals on vacations and trips to Cheapside
Save when you book Cheapside package deals
Cheapside flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Sea Breeze Beach House by Ocean Hotels - All Inclusive
Save 100% on your flight
Price was $2,005, price is now $1,176 per person
$1,176
per person
Dec 4 - Dec 7
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.
O2 Beach Club & Spa by Ocean Hotels - All Inclusive
Price was $3,508, price is now $1,796 per person
$1,796
per person
Nov 20 - Nov 23
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.
Concierge Collection at O2 Beach Club & Spa by Ocean Hotels
Price was $5,676, price is now $3,156 per person
$3,156
per person
Dec 5 - Dec 10
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.
Luxury Collection at Sea Breeze Beach House by Ocean Hotels
Save 100% on your flight
Price was $2,476, price is now $1,390 per person
$1,390
per person
Dec 4 - Dec 7
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.
Seacruise Villa
Save 100% on your flight
Price was $2,189, price is now $1,403 per person
$1,403
per person
Nov 1 - Nov 8
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
This villa doesn't skimp on freebies - guests receive free WiFi and free self parking. There's fun for all ages with a children's pool and an arcade/game room, and in-room childcare is an added bonus. Enjoy the outdoor pool and conveniences like a terrace and laundry facilities.
Top Cheapside hotels deals
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
$453 nightly
The price is $508 total per night
$508 total
Sep 28 - Sep 29
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.
Hilton Barbados Resort
Needhams Point, Bridgetown
Free Cancellation
Reserve now, pay when you stay
$295 nightly
The price is $331 total per night
$331 total
Oct 4 - Oct 5
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.
Sugar Bay Barbados - All Inclusive
Garrison Historic Area, Hastings
$670 nightly
The price is $747 total per night
$747 total
Oct 5 - Oct 6
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
The Crane Resort
Crane, Diamond Valley, St. Philip
Free Cancellation
Reserve now, pay when you stay
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.
Hilton Grand Vacations Club The Crane Barbados
The Crane Resort, Diamond Valley
$187 nightly
The price is $214 total per night
$214 total
Oct 15 - Oct 16
Total with taxes and fees
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.
Hotel Le Roy
St. Lawrence Gap, St. Lawrence Gap, Christ Church
$192 nightly
The price is $219 total per night
$219 total
Sep 28 - Sep 29
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, a communal living room, and luggage storage are also on offer.
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
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
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 lively bars.
Brighton Beach
Why not spend a carefree afternoon at Brighton Beach during your travels in Black Rock?
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