Chalk Sound Drive Vacations from $1,409

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The Latest Chalk Sound Drive vacation packages

Price found within the past 48 hours. Click for updated prices.
Windsong on the Reef

Windsong on the Reef

Grace Bay
$1,409
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
9.2/10 Wonderful! (1,207 reviews)
Rooftop Villa Collection

Rooftop Villa Collection

Grace Bay
$2,523
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
No reviews
Long Bay Beach Club

Long Bay Beach Club

Long Bay Hills
$5,869
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
10/10 Exceptional! (4 reviews)
.

Reviewed on Aug 3, 2026

Dream Villas Provo

Dream Villas Provo

Blue Hills
Save 100% on your flight
$1,872
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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

Beachfront at Windsong on the Reef

Beachfront at Windsong on the Reef

Grace Bay
Save 100% on your flight
$2,200
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Providenciales (PLS)
9.2/10 Wonderful! (176 reviews)
I’d recommend

Reviewed on Aug 12, 2026

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Chalk Sound Drive Hotel Deals

Escape to Exhale at a modern style villa with breathtaking views of chalk sound

Escape to Exhale at a modern style villa with breathtaking views of chalk sound

Providenciales Caicos Islands
Escape to Exhale at a modern style villa with breathtaking views of chalk sound
Modern Cottage with Chalk Sound Views

Modern Cottage with Chalk Sound Views

Providenciales
10/10 Exceptional! (22 reviews)
"Lovely home and incredible beach access and view!!"

Reviewed on Jun 26, 2026

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Modern Cottage with Chalk Sound Views
Designer Waterfront Villa with Sublime Views - Private & Exclusive. Free Kayaks.

Designer Waterfront Villa with Sublime Views - Private & Exclusive. Free Kayaks.

Providenciales Turks & Caicos
10/10 Exceptional! (1 review)
Relaxation
"Property was very private and taken care of well. Beautiful quiet home on the sound which was perfect for kayaking and relaxing. Property manager was very attentive and helpful. Highly recommend."

Reviewed on Mar 10, 2025

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Designer Waterfront Villa with Sublime Views - Private & Exclusive. Free Kayaks.
See all 1,688 properties in Chalk Sound Drive
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.

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