Leeward Settlement Vacations

Book a Hotel + Flight or Car together to unlock savings

    deals illustration

    Better together

    Save up to NT$5,067 when you book a flight and hotel together*
    stays illustration

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration

    Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Leeward Settlement

Find the best Leeward Settlement areas and neighborhoods for the activities you enjoy most. Learn more about Leeward Settlement
Grace Bay which includes a sandy beach, tropical scenes and a house

Grace Bay

3 out of top 10 points of interest in this area

This picturesque stretch of white sand and warm, turquoise water is home to luxury resorts, restaurants and one of the world’s largest barrier reefs.

Find hotels in Grace Bay

Leeward Settlement Hotel Deals

Blue Haven Resort - All Inclusive

Blue Haven Resort - All Inclusive

4.5 out of 5
Leeward Marina, Providenciales, Providenciales
The price is NT$26,323 per night from Aug 14 to Aug 15
NT$26,323
NT$26,323 total
Aug 14 - Aug 15
includes taxes & fees
8.8/10 Excellent! (668 reviews)
"Beautiful property. The food and dining options were all delicious! The staff was very friendly and accomodating."

Reviewed on 2025/7/9

Blue Haven Resort - All Inclusive
The Atrium Resort

The Atrium Resort

3.5 out of 5
Governor's Road, Leeward, Providenciales, Providenciales
8/10 Very Good! (202 reviews)
"Great property with full kitchen. Loved our stay and will return again."

Reviewed on 2025/6/24

Get rates
The Atrium Resort
Beach Enclave

Beach Enclave

5 out of 5
47 Joe Wood Drive, Providenciales
10/10 Exceptional! (3 reviews)
"Our recent stay at Beach Enclave North Shore was absolutely unforgettable. From the moment we arrived, we were captivated by the breathtaking beauty of the surroundings. The villa itself was stunning – spacious, luxurious, and impeccably maintained. The private pool and beach was a highlight, offering ..."

Reviewed on 2025/4/10

Get rates
Beach Enclave
See all 1,622 properties in Leeward Settlement
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.

Frequently asked questions

How much does a Leeward Settlement vacation package cost?
You can pick up a vacation package to this popular destination on Expedia. However, how much your vacation to Leeward Settlement costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Leeward Settlement?
Travel in the low or shoulder season and you're likely to find cheap Leeward Settlement vacation packages. Keep in mind that school vacation periods and local events and festivals can impact prices, so do a little research before booking.
How many days is enough for Leeward Settlement?
The ideal length for your Leeward Settlement vacation depends on what you'd like to do. Usually, a handful of days to a week will give you plenty of time to go to all the top sights and discover some hidden spots along the way.
How to find the best Leeward Settlement package deals?
Use Expedia's filter tool to help you find some of the best Leeward Settlement package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Leeward Settlement package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Leeward Settlement vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and stays individually. Better still, you can customize your Leeward Settlement getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Leeward Settlement?
Enjoy fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Leeward Settlement vacation.
How to plan a trip to Leeward Settlement?

  1. Choose the ideal time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to go to Leeward Settlement.
  2. Set a budget: Factor in expenses such as food, flights and transportation when working out how much to save for your trip to Leeward Settlement. Then, pick a hotel that matches your budget, whether that's a wallet-friendly option or a high-end retreat.
  3. Decide how long to go for: Now that you're up to speed on Leeward Settlement, you can figure out the ideal length of your break. Put together a rough plan and allocate enough time to get through everything on your must-do list.
  4. Combine your airfare and accommodations: After you've settled on your travel dates and duration, book the ideal Leeward Settlement vacation package for you.

Discover the most popular places to visit in Leeward Settlement

Grace Bay Beach featuring a beach

Grace Bay Beach

5/5(1,015 reviews)

Stretch out on fine white sands and marvel at the intense turquoise blue of the Caribbean waters on this pristine and photogenic stretch of shore.

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