Sterling Vacations from $890
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The Latest Sterling Vacation Packages
- East Resort
Jan 29 - Feb 3East Resort + Flight
St. Phillips5 nights3.5 star property8.6/10 - Excellent (7 reviews)"We loved the property. We have been to Barbados before and therefore understood the geography of where the East Resort is located. We stayed in a one bedroom villa. I’m not sure that the listing is comprehensive enough. The villa is beautiful, spacious, with lots of amenities in the room. The kitchen has a microwave, washing machine, tumble dryer, hot plate and fridge freezer. They leave you sugar, tea, coffee, milk, washing up liquid. The bathroom is beautiful. Shower no bath. Double sinks,..."Reviewed November 7, 2026Roundtrip • Boston (BOS) - Bridgetown (BGI)BOS - BGI • 1 stop BGI - BOS • 1 stop$1,539$890found 1 day agoper traveler - The Club, Barbados Resort & Spa Adults Only - All Inclusive
Jan 29 - Feb 3The Club, Barbados Resort & Spa Adults Only - All Inclusive + Flight
Holetown5 nights4.0 star property8.0/10 - Very good (605 reviews)"The hotel staff were very professional, attentive and FUN!!! The property was clean. There was no trash on the ground or overflowing trash cans. Our rooms were clean. However, our air conditioner did not keep the room cold it was extremely hot when we went and wanted to come back to a cold room."Reviewed November 8, 2026Roundtrip • Boston (BOS) - Bridgetown (BGI)BOS - BGI • 1 stop BGI - BOS • 1 stop$3,357$1,885found 1 day agoper traveler - Wyndham Grand Barbados Sam Lords Castle Resort
Jan 29 - Feb 3Wyndham Grand Barbados Sam Lords Castle Resort + Flight
Harrismith5 nights5.0 star property7.8/10 - Good (833 reviews)Roundtrip • Boston (BOS) - Bridgetown (BGI)BOS - BGI • 1 stop BGI - BOS • 1 stop$2,662$1,672found 1 day agoper traveler - Royalton Vessence Barbados Adult-Oriented, an Autograph Collection All-Inclusive Resort – Now Open
Jan 29 - Feb 3Royalton Vessence Barbados Adult-Oriented, an Autograph Collection All-Inclusive Resort – Now Open + Flight
Holetown5 nights5.0 star property7.4/10 - Good (67 reviews)"Everything was top tier."Reviewed November 9, 2026Roundtrip • Boston (BOS) - Bridgetown (BGI)BOS - BGI • 1 stop BGI - BOS • 1 stop$3,665$2,313found 1 day agoper traveler - Wild Cane Ridge 2 by Island Villas
Dec 10 - Dec 15Wild Cane Ridge 2 by Island Villas + Flight
Westmoreland5 nights4.5 star propertyRoundtrip • New York (NYC) - Bridgetown (BGI)JFK - BGI • Nonstop BGI - JFK • Nonstop$9,033$5,703found 21 hours agoper traveler
Sterling Hotel Deals
Hilton Grand Vacations Club The Crane Barbados
Hilton Grand Vacations Club The Crane Barbados"Exceptional stay at the Hilton Grand Crane Resort. Will definitely be back! Thank you Crane for an amazing vacation!"
Courtyard by Marriott Bridgetown, Barbados
Courtyard by Marriott Bridgetown, Barbados
"The resort offers a relaxed and informal atmosphere, featuring numerous dining and beverage options on the premises."
"The location was very good and decent"
"This "Santorini looking" resort took me by surprise. I liked that it was located in an almost secluded area. The peace and quiet was all that I wanted. I'll be staying here everytime I'm in Barbados. Thank you James and team."
"Great location, close to many restaurants."
Sea Breeze Beach House by Ocean Hotels
Sea Breeze Beach House by Ocean HotelsFrequently Asked Questions
How much does a Sterling vacation package cost?
You can grab a vacation package to this destination from $890 on Expedia. However, how much your vacation to Sterling costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Sterling?
September, November and December are the best times to look for cheap Sterling vacation packages. Opting to travel in quieter months means you'll typically find lower prices on hotels and flights.
How many days is enough for Sterling?
With a well-organized travel plan, you can easily visit the most popular Sterling sights in a handful of days. But if you'd like to discover lesser-known spots or go on day trips, consider booking your Sterling vacation for longer.
How to find the best Sterling package deals?
Use Expedia's filters to find some of the best Sterling package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Sterling package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Sterling vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging hotels and flights separately. Better still, you can tailor your Sterling getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Sterling?
Land amazing discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Sterling getaway.
Does Expedia offer Book Now, Pay Later Sterling vacation packages?
If you're like us, you love traveling the world but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Sterling vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.