Chalk Sound Drive Vacations from $1,896

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The Latest Chalk Sound Drive vacation packages

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

Dream Villas Provo

Blue Hills
Save 100% on your flight
$1,896
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
9.2/10 Wonderful! (79 reviews)
We had an incredible experience from booking to checkout! The Villas are located in an area that allows you privacy, but the convenience of still being close to dining, and other necessities. The check in and check out process were super simple, and they even made slight accommodations to help us when we had a flight delay. The villa has everything you might need in the kitchen if you choose to prepare meals there. We especially enjoyed the ability to walk steps off our sidewalk onto a beautiful beach, with included loungers, and water activity toys. Host response was always prompt, and again, accommodating to our changing needs. We wouldn’t hesitate to book this location again if we return to T&C.

Reviewed on Sep 24, 2026

Long Bay Beach Club

Long Bay Beach Club

Long Bay Hills
$9,075
per person
Nov 15 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
10/10 Exceptional! (4 reviews)
.

Reviewed on Aug 3, 2026

Rooftop Villa Collection

Rooftop Villa Collection

Grace Bay
Save 100% on your flight
$4,714
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
No reviews
Ambergris Cay Private Island - All-Inclusive

Ambergris Cay Private Island - All-Inclusive

Save 100% on your flight
$6,100
per person
Nov 29 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
9.8/10 Exceptional! (29 reviews)
Excellent place, excellent staff and beautiful private island. I cannot say a single bad thing about this place. We are planning to go back here every year. Thank you Ambergris Cay!

Reviewed on Sep 28, 2026

West Bay Club

West Bay Club

Grace Bay
Save 100% on your flight
$2,182
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
9.4/10 Exceptional! (1,003 reviews)
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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
9.4/10 Exceptional! (39 reviews)
"Overall, we had a good stay and the villa was just as pictured/listed. Check-in was pretty easy with the keypad, although the lockbox outside was a little difficult to access.The main issue was that the villa wasn’t clean when we first arrived. It was also a little difficult to reach the host through ..."

Reviewed on Sep 11, 2026

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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 1,710 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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