Sterling Vacation Packages

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Top Sterling Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Club, Barbados Resort & Spa Adults Only - All Inclusive

The Club, Barbados Resort & Spa Adults Only - All Inclusive

4 out of 5
Price was CA $3,682, price is now CA $1,670 per person
CA $1,670
per person
Sep 25 - Sep 30
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Bridgetown (BGI)
8/10 Very good! (533 reviews)
Good resort

Reviewed on Jul 15, 2026

East Resort

East Resort

3.5 out of 5
Price was CA $3,814, price is now CA $1,902 per person
CA $1,902
per person
Sep 27 - Oct 4
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Bridgetown (BGI)
5/10 (2 reviews)

Concierge Collection at O2 Beach Club & Spa by Ocean Hotels

Concierge Collection at O2 Beach Club & Spa by Ocean Hotels

5 out of 5
Price was CA $12,499, price is now CA $7,009 per person
CA $7,009
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Bridgetown (BGI)
8.8/10 Excellent! (39 reviews)
We understood that it was not peak vacation time in Barbados, but the resort was empty. The resort did not conduct any activities they had listed for the pool or the beach. No music being played - very low key. Restaurant choices very limited and one night there was even same menu two nights in a row. Very limited buffets. LOVED the staff at the spa! Definitely visit. The room was beautiful - very spacious and the view was wonderful.

Reviewed on Jul 6, 2026

Cobblers Cove - Barbados

Cobblers Cove - Barbados

5 out of 5
Price was CA $5,258, price is now CA $2,988 per person
CA $2,988
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Bridgetown (BGI)
9.4/10 Exceptional! (178 reviews)

Saint Peter's Bay

Saint Peter's Bay

5 out of 5
Price was CA $4,491, price is now CA $2,581 per person
CA $2,581
per person
Sep 21 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Bridgetown (BGI)
9.6/10 Exceptional! (168 reviews)
Our unit was amazing & very clean. The staff was extreamly friendly. Great place to enjoy a peaceful vacation!

Reviewed on Jul 12, 2026

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Sterling Hotel Deals

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort

5 out of 5
End of Belair Road Long Bay St. Philip
Fully refundableReserve now, pay when you stay
The price is CA $647 per night from Jul 20 to Jul 21
CA $647
CA $725 total
Jul 20 - Jul 21
includes taxes & fees
7.8/10 Good! (727 reviews)
"Everything was lovely"

Reviewed on Jul 15, 2026

Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort
Hilton Grand Vacations Club The Crane Barbados

Hilton Grand Vacations Club The Crane Barbados

4.5 out of 5
The Crane Resort Diamond Valley
Fully refundable
The price is CA $214 per night from Jul 27 to Jul 28
CA $214
CA $270 total
Jul 27 - Jul 28
includes taxes & fees
8.6/10 Excellent! (603 reviews)
"Great staff and customer service was next level."

Reviewed on Jul 15, 2026

Hilton Grand Vacations Club The Crane Barbados
Divi Southwinds Beach Resort

Divi Southwinds Beach Resort

3 out of 5
St Lawrence Main Road St. Lawrence Gap Christ Church
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Jul 23 to Jul 24
CA $151
CA $215 total
Jul 23 - Jul 24
includes taxes & fees
8/10 Very good! (868 reviews)
"Amazing staff from the moment we checked in. Stayed 8 days and would stay here again."

Reviewed on Jul 15, 2026

Divi Southwinds Beach Resort
See all 3,539 properties in Sterling
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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What to do in Sterling

Hotel Beach Day at Savvy with Shuttle Transfer

Hotel Beach Day at Savvy with Shuttle Transfer

CA $36
per adult
Hotel Beach Day at Savvy with Shuttle Transfer
Harbour Lights-Chair &Turtle Shipwreck Snorkel Tou

Harbour Lights-Chair &Turtle Shipwreck Snorkel Tour(10:30-1:30pm)

CA $56
per adult
80% of travellers recommend
Harbour Lights-Chair &Turtle Shipwreck Snorkel Tour(10:30-1:30pm)
Cave & Monkey Zipline Experience at Harrison's Cave by Chukka

Harrison's Cave Tour & Monkey Zipline, Barbados

CA $192
per adult
88% of travellers recommend
Harrison's Cave Tour & Monkey Zipline, Barbados
See all activities in Sterling

Frequently asked questions

How much does a Sterling vacation package cost?
You can grab a vacation package to this top destination from CA $1,670 on Expedia. However, how much your vacation to Sterling costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Sterling?
September, October and November are the best times to search for cheap Sterling vacation packages. Opting to travel in quieter months means you can generally find better prices on accommodations and flights.
How many days is enough for Sterling?
The ideal duration of your Sterling vacation depends on what you'd like to do. Typically, a handful of days to a week will give you time to check out all the major attractions and discover some hidden gems along the way.
How to find the best Sterling package deals?
Use Expedia's filter tool to help you find some of the best Sterling package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Sterling package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Sterling vacation as a package?
You can enjoy significant savings on your next Sterling retreat by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to view some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Sterling?
If you have your Sterling travel dates finalized, book as soon as you can to bag some unbeatable deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are great for quick escapes.
How to plan a trip to Sterling?

  1. Choose when to get away: Check your diary and get packing. Your preferred time of year and the activities on offer will also help you decide when to vacation in Sterling.
  2. Calculate your budget: Make sure you have enough money to cover everything from meals and transportation to flights and activities. Your hotel will probably be the largest expense during your trip to Sterling.
  3. Work out your trip length: Consider how much time you'd like to spend exploring Sterling. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customized Sterling vacation package.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.