Title: Book the Best Caribbean Islands WINERY Hotels in 2025 | Expedia.ca

  

[Caribbean Islands Travel Guide](https://expedia.ca/Caribbean-Islands.dx3000652683)[Hotels in Caribbean Islands](https://expedia.ca/Caribbean-Islands-Hotels.d3000652683.Travel-Guide-Hotels)[Vacation Rentals in Caribbean Islands](https://expedia.ca/Caribbean-Islands-Vacation-Rentals.d3000652683.Travel-Guide-VacationRentals)[Flights to Caribbean Islands](https://expedia.ca/Cheap-Flights-To-Caribbean-Islands.d3000652683.Travel-Guide-Flights)[Caribbean Islands Car Rentals](https://expedia.ca/Car-Rentals-In-Caribbean-Islands.d3000652683.Car-Rental-Guide)[Caribbean Islands Vacation Packages](https://expedia.ca/Caribbean-Islands.d3000652683.Destination-Travel-Guides)

![Anguilla featuring rocky coastline, a beach and tropical scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/25000/25736-Anguilla.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Find Winery Hotels in Caribbean Islands

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## Check availability on Caribbean Islands Winery Hotels

Tonight

[Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-10-15&endDate=2025-10-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-10-16&endDate=2025-10-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Caribbean Islands Winery Hotels

![Beach nearby, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/120000000/119860000/119859500/119859494/4cbfee1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119860000/119859500/119859494/abde848a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Studio, Pool View | Terrace/patio](https://images.trvl-media.com/lodging/120000000/119860000/119859500/119859494/09c306a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/120000000/119860000/119859500/119859494/f0e8ecca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### PUNTA CANA Paradise Studios BEACH POOL

Bávaro

10/10

Exceptional

(28)

"It was a great spot for our group getaway!!"

CA $145

CA $197 total

includes taxes & fees

Oct 16 - Oct 17

[](https://www.expedia.ca/Punta-Cana-Hotels-PUNTA-CANA-Paradise-Studios-BEACH-POOL.h119859494.Hotel-Information)

![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/14000000/13570000/13562100/13562088/5b33fc1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gym](https://images.trvl-media.com/lodging/14000000/13570000/13562100/13562088/dde7822c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sundeck](https://images.trvl-media.com/lodging/14000000/13570000/13562100/13562088/3573a8f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Courtyard](https://images.trvl-media.com/lodging/14000000/13570000/13562100/13562088/f48067d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Lodgings Hotel SureStay Collection by Best Western

Providenciales

7.6/10

Good

(568)

"Great place to stay "

CA $228

CA $289 total

includes taxes & fees

Oct 22 - Oct 23

[](https://www.expedia.ca/Providenciales-Hotels-The-Lodgings-Hotel-SureStay-Collection-By-Best-Western.h13562088.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/120000000/119570000/119561200/119561199/f6b70274.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Winery](https://images.trvl-media.com/lodging/120000000/119570000/119561200/119561199/2b28024b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Billiards](https://images.trvl-media.com/lodging/120000000/119570000/119561200/119561199/420d6857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/120000000/119570000/119561200/119561199/9fac8298.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Vista Bahia & Marina

Salinas

9.0/10

Wonderful

(2)

"Muy Bien"

CA $174

CA $197 total

includes taxes & fees

Oct 16 - Oct 17

[](https://www.expedia.ca/Salinas-Hotels-Hotel-Vista-Verde-And-Marina.h119561199.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/110000000/109850000/109847300/109847255/w3837h2557x3y4-c676216b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/110000000/109850000/109847300/109847255/w3836h2558x4y3-694aa831.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![40-inch Smart TV with cable channels, Netflix, Hulu](https://images.trvl-media.com/lodging/110000000/109850000/109847300/109847255/a0d946e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109850000/109847300/109847255/23d2b62b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Santiago, Curio Collection by Hilton

Villa Olga

9.6/10

Exceptional

(256)

"Definitely recommend 100% would definitely be back. The food at the restaurant was soo good, the staff were nice. "

CA $167

CA $214 total

includes taxes & fees

Oct 17 - Oct 18

[](https://www.expedia.ca/Santiago-De-Los-Caballeros-Hotels-Hotel-Santiago.h109847255.Hotel-Information)

![Outdoor pool, sun loungers, lifeguards on site](https://images.trvl-media.com/lodging/1000000/180000/173700/173653/09612f15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, Partial Ocean View](https://images.trvl-media.com/lodging/1000000/180000/173700/173653/87238c6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/180000/173700/173653/e3ec4da1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/180000/173700/173653/3a16fe1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Breezes Resort Bahamas All Inclusive

Nassau

7.6/10

Good

(1964)

"Another fantastic trip to Breezes, 4th time around and it’s just a fabulous time as always. Staff is incredibly nice, professional and accommodating, ready to book again in the spring!"

CA $432

CA $481 total

includes taxes & fees

Oct 21 - Oct 22

[](https://www.expedia.ca/Nassau-Hotels-Breezes-Resort-Bahamas.h173653.Hotel-Information)

![Arcade](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348106/a5c16f64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden view](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348106/w3543h2371x0y4-ce089178.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor wedding area](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348106/bc663ced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, pillowtop beds, free minibar](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348106/afd5267b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Paradisus Palma Real Golf & Spa Resort All Inclusive

Bávaro

8.6/10

Excellent

(1383)

"Nice pools, great ocean view, very friendly and professional staff."

CA $461

CA $590 total

includes taxes & fees

Oct 19 - Oct 20

[](https://www.expedia.ca/Punta-Cana-Hotels-Paradisus-Palma-Real-Golf-Spa-Resort-All-Inclusive.h1348106.Hotel-Information)

![Beach nearby, white sand, sun loungers, beach towels](https://images.trvl-media.com/lodging/17000000/16880000/16875000/16874964/9c9bc3df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/17000000/16880000/16875000/16874964/40c96745.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/17000000/16880000/16875000/16874964/f74f7173.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/17000000/16880000/16875000/16874964/a8bd5482.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Casa Hemingway

Villas Del Mar

9.6/10

Exceptional

(315)

"Beautiful place ...amazing security and staff"

CA $333

CA $427 total

includes taxes & fees

Oct 24 - Oct 25

[](https://www.expedia.ca/Guayacanes-Hotels-Hotel-Casa-Hemingway.h16874964.Hotel-Information)

![Rooftop terrace](https://images.trvl-media.com/lodging/88000000/87650000/87642900/87642846/w1076h1076x0y4-0a3788f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Rooftop terrace](https://images.trvl-media.com/lodging/88000000/87650000/87642900/87642846/2f9c3576.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/88000000/87650000/87642900/87642846/w1076h1075x0y7-b1c35e70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Double Room, 2 Queen Beds](https://images.trvl-media.com/lodging/88000000/87650000/87642900/87642846/w1076h1075x0y5-e5f4f1d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dinasty Hotel

Centro Histórico

8.0/10

Very good

(212)

"Staff was nice"

CA $53

CA $68 total

includes taxes & fees

Oct 16 - Oct 17

[](https://www.expedia.ca/Puerto-Plata-Hotels-Dinasty-Hotel.h87642846.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/115000000/114550000/114543900/114543876/aff9bc9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exercise/lap pool](https://images.trvl-media.com/lodging/115000000/114550000/114543900/114543876/8787aa36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/115000000/114550000/114543900/114543876/518d3440.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114550000/114543900/114543876/9f7b4ee7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### solmirooms

Santo Domingo Este

9.2/10

Wonderful

(16)

"Very friendly staff "

CA $70

CA $83 total

includes taxes & fees

Oct 16 - Oct 17

[](https://www.expedia.ca/Santo-Domingo-Hotels-Solmirooms.h114543876.Hotel-Information)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/13000000/12760000/12754600/12754554/5dc276b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/13000000/12760000/12754600/12754554/09c01f31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/13000000/12760000/12754600/12754554/4f40a8a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Twin Room](https://images.trvl-media.com/lodging/13000000/12760000/12754600/12754554/db9d2734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Karibu Aruba Boutique Hotel

Palm Beach

10/10

Exceptional

(118)

"We absolutely LOVED staying here in this wonderful location. The pool was just outside our door. We enjoyed a fab little kitchen. There’s a path to cross the street to the beach at the Marriott. This is also near the Ritz Carlton. Look and compare. My wife won $150.00 in the Marriott Casino. Near best beaches and sea turtles at Tres Trapi and California Lighthouse……Perfect for drone and photos at sunset. They are so gracious and helpful. We stayed 10 days."

CA $175

CA $211 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/Noord-Hotels-Karibu-Aruba-Boutique-Hotel.h12754554.Hotel-Information)

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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## Top Caribbean Islands Hotel Reviews