Title: Book the Best Caribbean Islands WINERY Hotels in 2026 | 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) ![Panoramic view of a tropical beach paradise with a calm sea and palm trees.](https://images.trvl-media.com/place/3000652683/0f906013-1c42-421c-97bc-ef4a41f0db0e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Caribbean Islands from CA $161 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](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) - ![](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 [Dec 27 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-12-27&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 28 - Dec 29](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2025-12-28&endDate=2025-12-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=3000652683&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Caribbean Islands hotels with winery ![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) ![Courtyard](https://images.trvl-media.com/lodging/14000000/13570000/13562100/13562088/f48067d6.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) ### The Lodgings Hotel SureStay Collection by Best Western [](https://www.expedia.ca/Providenciales-Hotels-The-Lodgings-Hotel-SureStay-Collection-By-Best-Western.h13562088.Hotel-Information) Providenciales 7.6/10 Good (598) "Although we only stayed one night, we had a wonderful stay. Great staff and super comfortable spotless accommodations. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gerald CA $246 CA $313 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Providenciales-Hotels-The-Lodgings-Hotel-SureStay-Collection-By-Best-Western.h13562088.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) ![View from room](https://images.trvl-media.com/lodging/110000000/109850000/109847300/109847255/a0d946e7.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) ![Restaurant](https://images.trvl-media.com/lodging/110000000/109850000/109847300/109847255/w3836h2558x4y3-694aa831.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Santiago, Curio Collection by Hilton [](https://www.expedia.ca/Santiago-De-Los-Caballeros-Hotels-Hotel-Santiago.h109847255.Hotel-Information) Villa Olga 9.6/10 Exceptional (361) "Very well located it , beautiful rooms and amazing staffđź‘Ťđź‘Ť" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Luis CA $174 CA $223 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Santiago-De-Los-Caballeros-Hotels-Hotel-Santiago.h109847255.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/17000000/16880000/16875000/16874964/f74f7173.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Casa Hemingway [](https://www.expedia.ca/Guayacanes-Hotels-Hotel-Casa-Hemingway.h16874964.Hotel-Information) Villas Del Mar 9.6/10 Exceptional (320) "Beautiful place ...amazing security and staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $334 CA $428 total includes taxes & fees Jan 26 - Jan 27, 2026 [](https://www.expedia.ca/Guayacanes-Hotels-Hotel-Casa-Hemingway.h16874964.Hotel-Information) ![2 outdoor pools](https://images.trvl-media.com/lodging/120000000/119570000/119561200/119561199/f4949836.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) ![Aerial view](https://images.trvl-media.com/lodging/120000000/119570000/119561200/119561199/f2683757.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/120000000/119570000/119561200/119561199/f6b70274.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Vista Bahia & Marina [](https://www.expedia.ca/Salinas-Hotels-Hotel-Vista-Verde-And-Marina.h119561199.Hotel-Information) Salinas 8.8/10 Excellent (31) "Great stay clean rooms had a lot of amenities to decompress" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Victor CA $184 CA $208 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Salinas-Hotels-Hotel-Vista-Verde-And-Marina.h119561199.Hotel-Information) ![Ecotours](https://images.trvl-media.com/lodging/123000000/122640000/122638000/122637974/c3357df7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, Poolside | Private kitchen](https://images.trvl-media.com/lodging/123000000/122640000/122638000/122637974/78692c39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite | View from room](https://images.trvl-media.com/lodging/123000000/122640000/122638000/122637974/bf6e2d6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/123000000/122640000/122638000/122637974/860f378f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CARIBBEAN Ocean Breeze Beach HOTEL [](https://www.expedia.ca/Punta-Cana-Hotels-CARIBBEAN-Ocean-Breeze-Beach-HOTEL.h122637974.Hotel-Information) Bávaro 10/10 Exceptional (7) "The combination of comfort, nature, and convenience makes this hotel very special. I will happily return again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paola CA $189 CA $269 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Punta-Cana-Hotels-CARIBBEAN-Ocean-Breeze-Beach-HOTEL.h122637974.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/109000000/108360000/108356600/108356545/d39d7d63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/109000000/108360000/108356600/108356545/w1429h960x0y2-c8e03af2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/109000000/108360000/108356600/108356545/w1236h960x0y0-44afb844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/109000000/108360000/108356600/108356545/w1388h942x0y0-fd5b8148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Alkquimia [](https://www.expedia.ca/San-Rafael-Del-Yuma-Hotels-Hotel-Alkquimia.h108356545.Hotel-Information) Bayahibe 9.0/10 Wonderful (23) "Good location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Juan CA $126 CA $161 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/San-Rafael-Del-Yuma-Hotels-Hotel-Alkquimia.h108356545.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) ![Suite Ocean Front | Beach/ocean view](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348106/e2b875ec.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) ![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) ### Paradisus Palma Real Golf & Spa Resort All Inclusive [](https://www.expedia.ca/Punta-Cana-Hotels-Paradisus-Palma-Real-Golf-Spa-Resort-All-Inclusive.h1348106.Hotel-Information) Bávaro 8.6/10 Excellent (1473) "One of the best all inclusive resorts i have had the pleasure in staying with my family." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Luanel CA $531 CA $680 total includes taxes & fees Jan 24 - Jan 25, 2026 [](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 umbrellas](https://images.trvl-media.com/lodging/120000000/119860000/119859500/119859494/fcd6cb45.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) ![Exterior](https://images.trvl-media.com/lodging/120000000/119860000/119859500/119859494/cb89eb09.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 [](https://www.expedia.ca/Punta-Cana-Hotels-PUNTA-CANA-Paradise-Studios-BEACH-POOL.h119859494.Hotel-Information) Bávaro 10/10 Exceptional (42) "It was a great spot for our group getaway!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katrina CA $198 CA $258 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Punta-Cana-Hotels-PUNTA-CANA-Paradise-Studios-BEACH-POOL.h119859494.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/60000000/59950000/59946400/59946372/5a877fe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/60000000/59950000/59946400/59946372/27bb2e64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Two Bedroom Suite, 2 King Beds and 1 Sofa Bed, Kitchen, Oceanfront (Residence)](https://images.trvl-media.com/lodging/60000000/59950000/59946400/59946372/a20a3bd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, Select Comfort beds](https://images.trvl-media.com/lodging/60000000/59950000/59946400/59946372/bf0e0def.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Margaritaville Beach Resort - Nassau [](https://www.expedia.ca/Nassau-Hotels-Margaritaville-Beach-Resort-Nassau.h59946372.Hotel-Information) Downtown Nassau 8.4/10 Very good (2238) "Very much enjoyed our stay. Beautiful resort and extremely nice staff. Fabulous beach and crystal clear water. Waterpark was very fun. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Amanda CA $360 CA $556 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Nassau-Hotels-Margaritaville-Beach-Resort-Nassau.h59946372.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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/180000/173700/173653/a487eb90.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) ![Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/180000/173700/173653/87238c6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Breezes Resort Bahamas All Inclusive [](https://www.expedia.ca/Nassau-Hotels-Breezes-Resort-Bahamas.h173653.Hotel-Information) Nassau 7.6/10 Good (2025) "We loved it so much that we are planning our next stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather CA $484 CA $535 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Nassau-Hotels-Breezes-Resort-Bahamas.h173653.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=2026-01-10&endDate=2026-01-11®ionId=3000652683&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Caribbean Islands Hotel Reviews