Leeward Settlement Holidays

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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.

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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 €672 per night from 26 Nov to 27 Nov
€672
26 Nov - 27 Nov
includes taxes & fees
8.8/10 Excellent! (678 reviews)
Overall it was ok. Food was ok. A lot of mosquitos.

Reviewed on 2 Sept 2025

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! (207 reviews)
Close to the beach

Reviewed on 30 Sept 2025

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The Atrium Resort
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
See all 1,665 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 beautiful beaches in this relaxing 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 beautiful beaches or discover the spectacular coral reefs in this relaxing area.

The Regent Village Shopping Mall

Things to do

4hour Group Half Day Snorkeling Excursion in Grace Bay

4hour Group Half Day Snorkeling Excursion in Grace Bay

€107
per adult
92% of travellers recommend
4hour Group Half Day Snorkeling Excursion in Grace Bay
4-Hour Catamaran Sail and Snorkel Tour from Grace Bay

4-Hour Catamaran Sail and Snorkel Tour from Grace Bay

€125
per adult
96% of travellers recommend
4-Hour Catamaran Sail and Snorkel Tour from Grace Bay
Half-Day Snorkeling & Conch Cruise with Beach Picnic

Half-Day Snorkeling Cruise

€126
per adult
94% of travellers recommend
Half-Day Snorkeling Cruise
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.