Westmoreland Vacations from $1,368

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Your Westmoreland Vacation

Take the hassle out of travel planning by booking a Westmoreland vacation package. A great neighborhood to stay in this amazing city is Upper Carlton, which is great for walking and much more. If your trip to Westmoreland includes some sightseeing, hit up popular attractions like Sandy Lane Beach, Paynes Bay Beach and Holetown Beach. No matter your travel plans or the size of your budget, organizing a tailored Westmoreland vacation is a cinch with Expedia.

The Latest Westmoreland vacation packages

Price found within the past 48 hours. Click for updated prices.
Oceanfront 2-bed Apt With Pool Near Surfing - Rosalie #2 2 Bedroom Apts by Bluescape

Oceanfront 2-bed Apt With Pool Near Surfing - Rosalie #2 2 Bedroom Apts by Bluescape

3.5 out of 5
Green Garden
Price was $3,146, price is now $1,368 per person
$1,368
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Bridgetown (BGI)
No 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 $6,260, price is now $3,226 per person
$3,226
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
9/10 Wonderful! (36 reviews)
The staff was exceptionally friendly and professional. Location is great if you want peace and quiet; it’s not near too many other resorts. There are clubs nearby, outdoor which allows you to enjoy the outdoor air and environment. You have to take a taxi to go from the resort to downtown or walk maybe quarter a mile to bus transportation, which was easy to use.

Reviewed on Sep 15, 2025

O2 Beach Club & Spa by Ocean Hotels - All Inclusive

O2 Beach Club & Spa by Ocean Hotels - All Inclusive

5 out of 5
Price was $7,140, price is now $3,689 per person
$3,689
per person
Mar 15 - Mar 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
8.8/10 Excellent! (192 reviews)
Hotel was wonderful, our room was everything we could have asked for and more with beautiful views of the beach and stunning sunset every day. The staff were fantastic, super friendly and helpful they all made us feel right at home and like we could ask anything anytime. Great food, great entertainment ( New Year’s Eve was brilliant) and great location. Will be back very soon

Reviewed on Jan 4, 2026

Sea Breeze Beach House by Ocean Hotels - All Inclusive

Sea Breeze Beach House by Ocean Hotels - All Inclusive

4 out of 5
Price was $3,501, price is now $1,827 per person
$1,827
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
8.4/10 Very Good! (367 reviews)
Staff willingness to make your stay comfortable.

Reviewed on Dec 30, 2025

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

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

4 out of 5
Save 100% on your flight
Price was $2,845, price is now $1,539 per person
$1,539
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Bridgetown (BGI)
8/10 Very Good! (445 reviews)
Very nice resort. There are only stairs

Reviewed on Jan 3, 2026

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Discover the most popular places to visit in Westmoreland

Royal Westmoreland Golf Course

Play a round of golf in Westmoreland at Royal Westmoreland Golf Course, and enjoy other activities such as snorkeling. Wander the beautiful beaches or discover the area's beautiful sunsets.

Royal Westmoreland Golf Course

What to do in Westmoreland

Barbados -Luxury Cruise with Lunch and Open Bar

Barbados -Luxury Cruise with Lunch and Open Bar By Oceanluxx

$125
per adult
100% of travellers recommend
Barbados -Luxury Cruise with Lunch and Open Bar By Oceanluxx
A Guided Walking Tour of The History of a City – Bridgetown

Bridgetown: A Guided Walking Tour of The History of a City

$25
per adult
98% of travellers recommend
Bridgetown: A Guided Walking Tour of The History of a City
Monkey Feeding

Barbados Shore Excursion: Wildlife Encounter and Beach Day

$78
per adult
Barbados Shore Excursion: Wildlife Encounter and Beach Day
See all activities in Westmoreland

Westmoreland Hotel Deals

The Crane Resort

The Crane Resort

4.5 out of 5
Crane Diamond Valley St. Philip
Fully refundableReserve now, pay when you stay
$611 nightly
The price is $681 total per night from Jan 22 to Jan 23
$681 total
Jan 22 - Jan 23
Total with taxes and fees
8.4/10 Very Good! (1,005 reviews)
Fabulous. Best resort we’ve ever experienced

Reviewed on Jan 10, 2026

The Crane Resort
Hilton Barbados Resort

Hilton Barbados Resort

4.5 out of 5
Needhams Point Bridgetown
Fully refundableReserve now, pay when you stay
$527 nightly
The price is $584 total per night from Jan 19 to Jan 20
$584 total
Jan 19 - Jan 20
Total with taxes and fees
8.2/10 Very Good! (1,015 reviews)
Amazing! Clean, and everyone is friendly.

Reviewed on Jan 10, 2026

Hilton Barbados Resort
South Point Hotel

South Point Hotel

4.5 out of 5
100 Ocean Way, Silver Sands Oistins Christ Church
Fully refundableReserve now, pay when you stay
$326 nightly
The price is $363 total per night from Feb 10 to Feb 11
$363 total
Feb 10 - Feb 11
Total with taxes and fees
9/10 Wonderful! (112 reviews)
The staff was wonderful. We arrived at 11:00 pm. Our flight came in late and we still were served with a rum punch (the bar was already closed). Our reception girl was awesome! We came with friends and the hotel managed to get our rooms together. The property is landscaped nicely. The onsite restaurant ...

Reviewed on Jan 12, 2026

South Point Hotel
See all 3,571 properties in Westmoreland
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.

Find the Best Westmoreland Vacation Packages

Westmoreland Essential Information

Language
English
Currency
Barbadian dollars
Closest Airport
Grantley Adams Intl. Airport (BGI)
Max Temp Winter
80ºF
Max Temp Summer
80ºF
Top Sights
Sandy Lane Beach, Paynes Bay Beach and Holetown Beach

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Frequently asked questions

How much does a Westmoreland vacation package cost?
Offering excellent value package deals from $1,368 on Expedia, you'll be thrilled with how little a vacation to Westmoreland costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Westmoreland?
February, April and December are the best times to look for cheap Westmoreland vacation packages. Opting to travel in quieter months means you can usually find better prices on flights and accommodations.
How many days is enough for Westmoreland?
Typically, a handful of days is enough to go to the main attractions during your Westmoreland vacation. However, if you prefer to have time to kick back or take day tours, think about extending your itinerary.
How to find the best Westmoreland package deals?
Use Expedia's filters to find some unbeatable Westmoreland 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 escape for midweek, or search for Westmoreland package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Westmoreland vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component individually. And you'll still have the flexibility to create a customized Westmoreland vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Westmoreland?
If you're planning a spontaneous Westmoreland getaway, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Westmoreland?

  1. Choose when to travel: Check your diary and get packing. Your preferred season and the available activities will also help you decide when to escape to Westmoreland.
  2. Calculate your budget: Make sure you have enough money to cover everything from transportation and meals to experiences and flights. Your accommodations will probably be the biggest expense during your trip to Westmoreland.
  3. Use our trip planning tool to discover Westmoreland: Research every part of your trip to Westmoreland with this handy planner. Invite your friends and family to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Decide how long to go away for: Now that you're more familiar with Westmoreland, you can work out the perfect length of your break. Put together a draft itinerary and allocate enough time for all the things you want to do.
  5. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to choose a Westmoreland vacation package that brings all your bookings together.
  6. Add on experiences and excursions: Read our travel guide to find some fun things to do in Westmoreland. Book tickets or make reservations before you go to save time and avoid the hassle of searching for activities when you arrive.

Does Expedia offer Book Now, Pay Later Westmoreland vacation packages?
If you're anything like us, you love exploring new places but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Westmoreland trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.