Leeward Settlement Holidays

Book a Hotel + Flight or Car together to unlock savings

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 house, a beach and tropical scenes

Grace Bay

3 out of top 10 points of interest in this area

Amazing beaches island views and top sights from Grace Bay Beach to The Regent Village – discover Grace Bay, a destination also famous for its snorkelling.

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Top hotels in Leeward Settlement

Blue Haven Resort - All-Inclusive

Blue Haven Resort - All-Inclusive

4.5 out of 5
Leeward Marina Providenciales Providenciales
The price is 26.075.643 ₫ per night from 7 Jan to 8 Jan
26.075.643 ₫
26.075.643 ₫ total
7 Jan - 8 Jan 2026
includes taxes & fees
8.8/10 Excellent! (686 reviews)
Beach front location is great,big shout out to Natalie at the pool bar!!

Reviewed on 2 Dec 2025

Blue Haven Resort - All-Inclusive
Checkers Vacation Homes

Checkers Vacation Homes

3 out of 5
63 Grace Bay Road Providenciales Providenciales
7/10 Good! (33 reviews)
I loved the homey feel, with the fully equipped kitchen and AC. Quiet place

Reviewed on 13 Jun 2025

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Checkers Vacation Homes
The Atrium Resort

The Atrium Resort

3.5 out of 5
Governor's Road Providenciales Providenciales
8/10 Very Good! (207 reviews)
Close to the beach

Reviewed on 30 Sept 2025

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The Atrium Resort
See all 1,674 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

Pelican Beach

Pelican Beach

Why not spend a care-free afternoon at Pelican Beach during your travels in Turtle Cove? Discover the coral reefs while you're in the area.

Pelican Beach
Chalk Sound National Park

Chalk Sound National Park

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

Chalk Sound National Park

Provo Conch Farm

You can learn about the history of Providenciales with a visit to Provo Conch Farm. Stroll along the seaside or discover the spectacular coral reefs in this romantic area.

Provo Conch Farm