Leeward Settlement Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    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 showing a 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

Top hotels in Leeward Settlement

Blue Haven Resort - All Inclusive

Blue Haven Resort - All Inclusive

4.5 out of 5
Leeward Marina, Providenciales, Providenciales
Get rates
Blue Haven Resort - All Inclusive
The Atrium Resort

The Atrium Resort

3.5 out of 5
Governor's Road, Leeward, Providenciales, Providenciales
Get rates
The Atrium Resort
Barefoot Luxury – Silver Palms Cottage # 1, Beachfront with Pool on Long Bay

Barefoot Luxury – Silver Palms Cottage # 1, Beachfront with Pool on Long Bay

providenciales
Get rates
Barefoot Luxury – Silver Palms Cottage # 1, Beachfront with Pool on Long Bay
See all 1,642 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 holiday package cost?
You can pick up a holiday package to this popular destination on Expedia. However, how much your holiday 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 holiday packages. Keep in mind that school holiday 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 holiday 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 holiday package as soon as possible.
Is it cheaper to book a Leeward Settlement holiday as a package?
An Expedia holiday package could land you considerable savings when compared to arranging flights and stays individually. Better still, you can customise 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 holiday 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 holiday.
How to plan a trip to Leeward Settlement?

  1. Choose the ideal time to travel: Your schedule, favourite 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 accommodation: After you've settled on your travel dates and duration, book the ideal Leeward Settlement holiday package for you.

Popular places to visit

Chalk Sound

Chalk Sound

Explore the great outdoors at Chalk Sound, a lovely green space in Providenciales. Stroll along the seaside in this romantic area or seek out the snorkelling spots.

Chalk Sound

Long Bay Beach

Why not spend a care-free afternoon at Long Bay Beach during your travels in Long Bay Hills? Make some time to visit the shops while you're in the area.

Long Bay Beach

The Regent Village Shopping Mall

4/5(3 reviews)

You can enjoy retail therapy at The Regent Village Shopping Mall during your trip to Providenciales. Stroll along the seaside or discover the spectacular coral reefs in this romantic area.

The Regent Village Shopping Mall

Things to do

Clear Kayak Drone Photoshoot

Clear Kayak Drone Photoshoot

€117
per adult
80% of travellers recommend
Clear Kayak Drone Photoshoot
Clear Kayak Tour in Turks & Caicos Islands

Clear Kayak Tour in Turks & Caicos Islands

€99
per adult
Clear Kayak Tour in Turks & Caicos Islands
3HR Emerald reef snorkeling, iguana island and shipwreck tour

3HR Emerald reef snorkeling, iguana island and shipwreck tour

€96
per adult
3HR Emerald reef snorkeling, iguana island and shipwreck tour
See all activities in Providenciales
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.