Vacations Close To Cheshire Hall Plantation

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Cheshire Hall Plantation Flight + Hotel packages

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

Windsong on the Reef

4.5 out of 5
Grace Bay
Save 100% on your flight
Price was $2,368, price is now $1,473 per person
$1,473
per person
Dec 13 - Dec 17
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
Place is amazing. Staff is amazing, Amenities and rooms and view are amazing. Some wait for food service at restaurants, but that comes with the island territory which we Americans are so used to fast service.

Reviewed on Oct 19, 2026

Dream Villas Provo

Dream Villas Provo

3.5 out of 5
Blue Hills
Save 100% on your flight
Price was $6,028, price is now $3,410 per person
$3,410
per person
Nov 18 - Nov 25
found 21 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Providenciales (PLS)

Beachfront at Windsong on the Reef

Beachfront at Windsong on the Reef

5 out of 5
Grace Bay
Save 100% on your flight
Price was $3,229, price is now $1,949 per person
$1,949
per person
Dec 13 - Dec 17
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
Great location and service

Reviewed on Oct 19, 2026

The Strand Turks and Caicos

The Strand Turks and Caicos

5 out of 5
Cooper Jack Bay Settlement
Save 100% on your flight
Price was $3,816, price is now $2,340 per person
$2,340
per person
Dec 13 - Dec 17
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
Place was Amazing!!

Reviewed on Oct 14, 2026

Bungalows at Windsong on the Reef

Bungalows at Windsong on the Reef

4 out of 5
Grace Bay
Save 100% on your flight
Price was $3,349, price is now $2,200 per person
$2,200
per person
Dec 13 - Dec 17
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)
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

The Palms Turks and Caicos

The Palms Turks and Caicos

5 out of 5
Grace Bay
Save 100% on your flight
Price was $3,238, price is now $2,258 per person
$2,258
per person
Dec 13 - Dec 17
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)

Rooftop Villa Collection

Rooftop Villa Collection

5 out of 5
Grace Bay
Save 100% on your flight
Price was $8,031, price is now $5,602 per person
$5,602
per person
Dec 13 - Dec 17
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)

Le Vele Resort

Le Vele Resort

4 out of 5
Grace Bay
Save 100% on your flight
Price was $2,717, price is now $1,900 per person
$1,900
per person
Dec 13 - Dec 17
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Providenciales (PLS)

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Best Lodging Options Near Cheshire Hall Plantation

Rock House

Rock House

5 out of 5
1 International Drive Providenciales
1.25 km from Cheshire Hall Plantation
Book a stay at this luxury hotel in Providenciales. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Zenza Boutique Hotel

Zenza Boutique Hotel

4 out of 5
Bridge Rd. Providenciales Caicos Islands
2.79 km from Cheshire Hall Plantation
Stay at this hotel in Providenciales. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. ...
The Lodgings Hotel SureStay Collection by Best Western

The Lodgings Hotel SureStay Collection by Best Western

3 out of 5
Williams Plaza Providenciales
1.03 km from Cheshire Hall Plantation
Book a stay at this spa hotel in Providenciales. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Grace Bay Beach and Turtle Cove Marina ...
Wymara Resort and Villas

Wymara Resort and Villas

5 out of 5
Lower Bight Road Providenciales Providenciales
4.34 km from Cheshire Hall Plantation
Book a stay at this luxury resort in Providenciales. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Le Bleu Bed and Breakfast

Le Bleu Bed and Breakfast

3 out of 5
30 Five Cays Rd Providenciales Caicos Islands
1.53 km from Cheshire Hall Plantation
Stay at this B&B in Providenciales. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Grace Bay Beach and Turtle Cove Marina are located ...
Windsong on the Reef

Windsong on the Reef

4.5 out of 5
Stubbs Rd Providenciales Providenciales
5.05 km from Cheshire Hall Plantation
Book a stay at this luxury resort in Providenciales. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Villas at Blue Mountain

Villas at Blue Mountain

5 out of 5
Azure Court, Blue Mountain Rd Providenciales
1.14 km from Cheshire Hall Plantation
Book a stay at this luxury villa in Providenciales. Enjoy free WiFi, free parking, and private pools. Popular attractions Grace Bay Beach and Turtle Cove Marina ...
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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.