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

![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg)

### 

Change your mind

Book hotels with free cancellation

![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg)

### 

Treat yourself

Sign in to save 10% or more on thousands of hotels

[Sign in](https://www.expedia.ca/login)

![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg)

### 

Be picky

Search almost a million properties worldwide

## Check availability on Caribbean Islands Winery Hotels

Tonight

[Sep 27 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-09-27&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Sep 28 - Sep 29](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-09-28&endDate=2025-09-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Caribbean Islands Winery Hotels

![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)

![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)

![Meeting facility](https://images.trvl-media.com/lodging/110000000/109850000/109847300/109847255/w3836h2557x4y4-5dc9718e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Santiago, Curio Collection by Hilton

Villa Olga

9.6/10

Exceptional

(223)

"Amazing place to stay "

CA $166

CA $213 total

includes taxes & fees

Sep 29 - Sep 30

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

![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)

![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)

![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

9.0/10

Wonderful

(14)

"Very friendly staff "

CA $70

CA $82 total

includes taxes & fees

Sep 28 - Sep 29

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

![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/cb89eb09.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)

### PUNTA CANA Paradise Studios BEACH POOL

Bávaro

10/10

Exceptional

(7)

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

CA $144

CA $195 total

includes taxes & fees

Sep 28 - Sep 29

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

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

![5 restaurants, breakfast, lunch, dinner served; Spanish cuisine](https://images.trvl-media.com/lodging/17000000/16880000/16875000/16874964/b610e9c6.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)

### Hotel Casa Hemingway

Villas Del Mar

9.6/10

Exceptional

(312)

"Beautiful place ...amazing security and staff"

CA $248

CA $318 total

includes taxes & fees

Oct 27 - Oct 28

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

![Sundeck](https://images.trvl-media.com/lodging/14000000/13570000/13562100/13562088/3573a8f8.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)

![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

(562)

"Great place to stay "

CA $226

CA $287 total

includes taxes & fees

Oct 3 - Oct 4

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

![1 bedroom, minibar, desk, laptop workspace](https://images.trvl-media.com/lodging/31000000/30060000/30053800/30053706/bbead682.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/31000000/30060000/30053800/30053706/c4144670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/31000000/30060000/30053800/30053706/e47398af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gym](https://images.trvl-media.com/lodging/31000000/30060000/30053800/30053706/2acc5283.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Tibisay Hotel Boutique Margarita

Playa Moreno

CA $319

CA $319 total

includes taxes & fees

Sep 28 - Sep 29

[](https://www.expedia.ca/Maneiro-Hotels-Tibisay-Hotel-Boutique-Margarita.h30053706.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/104000000/103390000/103384000/103383987/cf9acab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, blackout drapes, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/104000000/103390000/103384000/103383987/6a792e3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/104000000/103390000/103384000/103383987/e91b89db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/104000000/103390000/103384000/103383987/5ef3d5a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kimpton Las Mercedes by IHG

Zona Colonial

9.4/10

Exceptional

(126)

"beautiful place!"

CA $200

CA $255 total

includes taxes & fees

Oct 6 - Oct 7

[](https://www.expedia.ca/Santo-Domingo-Hotels-Kimpton-Las-Mercedes.h103383987.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)

![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)

![Exterior](https://images.trvl-media.com/lodging/88000000/87650000/87642900/87642846/w1076h1075x0y7-b1c35e70.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)

### Dinasty Hotel

Centro Histórico

7.8/10

Good

(211)

"Staff was nice"

CA $53

CA $68 total

includes taxes & fees

Sep 28 - Sep 29

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

![Front of property](https://images.trvl-media.com/lodging/71000000/70590000/70584900/70584832/fe6b45f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![99-cm flat-screen TV with satellite channels, TV](https://images.trvl-media.com/lodging/71000000/70590000/70584900/70584832/7e69495c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, Tempur-Pedic beds](https://images.trvl-media.com/lodging/71000000/70590000/70584900/70584832/b6c538fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/71000000/70590000/70584900/70584832/deb07eba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chez Lilly

Ponton

10/10

Exceptional

(2)

"I booked this stay for a short night to escape a bad situation and the host was so wonderful and kind to me. She upgraded my room and drove me directly to the airport the next morning. I was comfortable and safe!"

CA $135

CA $157 total

includes taxes & fees

Sep 28 - Sep 29

[](https://www.expedia.ca/Oranjestad-Hotels-Chez-Lilly.h70584832.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/121000000/120070000/120069100/120069055/b24286ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120070000/120069100/120069055/92a479e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120070000/120069100/120069055/3449ce36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach](https://images.trvl-media.com/lodging/121000000/120070000/120069100/120069055/895d2f7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Penthouse en el Paraiso.

Bávaro

CA $110

CA $130 total

includes taxes & fees

Sep 28 - Sep 29

[](https://www.expedia.ca/Punta-Cana-Hotels-Penthouse-En-El-Paraiso.h120069055.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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-11&endDate=2025-10-12&regionId=3000652683&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true)

## Top Caribbean Islands Hotel Reviews