Chalk Sound Drive Luxury Vacations

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Flight and Luxury hotel deals in Chalk Sound Drive

Price found within the past 48 hours. Click for updated prices.
Zenza Boutique Hotel

Zenza Boutique Hotel

Turtle Cove
CA $1,824
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Providenciales (PLS)
9.4/10 Exceptional! (865 reviews)
Long Bay Beach Club

Long Bay Beach Club

Long Bay Hills
CA $12,683
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Providenciales (PLS)
10/10 Exceptional! (4 reviews)
.

Reviewed on Aug 3, 2026

Bungalows at Windsong on the Reef

Bungalows at Windsong on the Reef

Grace Bay
CA $3,258
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Providenciales (PLS)
9/10 Wonderful! (101 reviews)
We had an AMAZING stay. The property is well maintained. Amenities convenient. Food GOOD. Staff EXCEPTIONAL! Shout Out to Raheem!

Reviewed on Aug 6, 2026

Beach Enclave

Beach Enclave

Leeward Settlement
CA $7,060
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Providenciales (PLS)
8/10 Very good! (11 reviews)
Point Grace

Point Grace

Grace Bay
CA $4,581
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Providenciales (PLS)
9.6/10 Exceptional! (342 reviews)
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5* Luxury holidays in Chalk Sound Drive

Price found within the past 48 hours. Click for updated prices.
Rooftop Villa Collection

Rooftop Villa Collection

Grace Bay
CA $4,473
per person
Oct 23 - Oct 27
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Providenciales (PLS)
No reviews
Long Bay Beach Club

Long Bay Beach Club

Long Bay Hills
CA $12,683
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Providenciales (PLS)
10/10 Exceptional! (4 reviews)
.

Reviewed on Aug 3, 2026

Beach Enclave

Beach Enclave

Leeward Settlement
CA $7,060
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Providenciales (PLS)
8/10 Very good! (11 reviews)
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3 Night Luxury holidays in Chalk Sound Drive

Price found within the past 48 hours. Click for updated prices.
The Shore Club Turks and Caicos

The Shore Club Turks and Caicos

Long Bay Hills
CA $1,447
per person
Oct 5 - Oct 8
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Providenciales (PLS)
9.4/10 Exceptional! (965 reviews)
Amazing hotel to stay, from the moment you arrive to you leave. The staff are amazing and friendly. The rooms are very clean,comfortable and beautiful. Perfect place to relax and enjoy.

Reviewed on Aug 20, 2026

Long Bay Beach Club

Long Bay Beach Club

Long Bay Hills
CA $3,507
per person
Oct 25 - Oct 28
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Providenciales (PLS)
10/10 Exceptional! (4 reviews)
.

Reviewed on Aug 3, 2026

Rooftop Villa Collection

Rooftop Villa Collection

Grace Bay
CA $3,482
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Providenciales (PLS)
No reviews
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4 Night Luxury holidays in Chalk Sound Drive

Price found within the past 48 hours. Click for updated prices.
Dream Villas Provo

Dream Villas Provo

Blue Hills
CA $2,693
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Providenciales (PLS)
9.2/10 Wonderful! (76 reviews)
I would recommend this place for a relaxing getaway; it’s not really suited for those who prefer an active vacation. The house itself is great—good soundproofing and plenty of air conditioning units that handle the heat well. It was generally well-equipped. It was clean, with no insects or unpleasant odors. The rooftop pool was always cooler than the ocean, which was very refreshing in the heat. Parking was along the road; we had no issues with our car over the course of the week. The water was very warm in August—no need to acclimate to the temperature at all. Communication with the owners was smooth and easy. There were sometimes stray dogs outside, but they were calm and friendly; they didn't try to enter the house or bark. Driving on the island is very easy, even though everyone drives at twice the speed limit; I only saw the police a couple of times.One thing I didn't love—though this is more about the trip in general than the house—was the weather: it was hotter than usual (30°C / 86°F) with high humidity, so it was best to spend the hours between 11:00 AM and 4:00 PM resting indoors or having lunch. The best times to be outside were 7:00–10:00 AM and 4:00–7:00 PM. The sun loungers on the roof aren't the newest and are dusty, but if you use beach towels, there’s no problem. There were rains, but they were very brief and light. There was quite a bit of broken glass on the beach; over the course of the week, we collected and removed the shards ourselves.

Reviewed on Aug 14, 2026

Long Bay Beach Club

Long Bay Beach Club

Long Bay Hills
CA $8,525
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Providenciales (PLS)
10/10 Exceptional! (4 reviews)
.

Reviewed on Aug 3, 2026

Rooftop Villa Collection

Rooftop Villa Collection

Grace Bay
CA $4,473
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Providenciales (PLS)
No reviews
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Plan the perfect luxury Chalk Sound Drive vacation with Expedia

What are some benefits when booking luxury Chalk Sound Drive vacations?

When you book a luxury Chalk Sound Drive vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.

How can I find all-inclusive luxury vacations in Chalk Sound Drive?

If you're looking for something luxurious in Chalk Sound Drive, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.

Can I book a cheap luxury vacation?

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $1,447, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 33. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.

Are there luxury spa vacations?

Yes, luxury spa vacations are available and quite popular in Chalk Sound Drive. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.

What should I look for in a luxury family vacation in Chalk Sound Drive?

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Chalk Sound Drive.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Chalk Sound Drive. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

What can help me find the best luxury vacation deals in Chalk Sound Drive?

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Chalk Sound Drive or travelling to more obscure destinations altogether can often lead to lower prices.

Can I book a luxury vacation that is fully refundable?

Yes, fully refundable reservations are sometimes available on luxury vacation packages in Chalk Sound Drive. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.

Why should I book my luxury vacation with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.

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