Title: Book the Best Greek Islands WINERY Hotels in 2026 | Expedia.ca [Greek Islands Travel Guide](https://expedia.ca/Greek-Islands.dx6271742)[Hotels in Greek Islands](https://expedia.ca/Greek-Islands-Hotels.d6271742.Travel-Guide-Hotels)[Vacation Rentals in Greek Islands](https://expedia.ca/Greek-Islands-Vacation-Rentals.d6271742.Travel-Guide-VacationRentals)[Flights to Greek Islands](https://expedia.ca/Cheap-Flights-To-Greek-Islands.d6271742.Travel-Guide-Flights)[Greek Islands Car Rentals](https://expedia.ca/Car-Rentals-In-Greek-Islands.d6271742.Car-Rental-Guide)[Greek Islands Vacation Packages](https://expedia.ca/Greek-Islands.d6271742.Destination-Travel-Guides) ![Paleokastritsa Beach showing general coastal views](https://images.trvl-media.com/place/6105704/ed59c85e-33c3-4f6e-88d7-af5b4373672d.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6105704/ed59c85e-33c3-4f6e-88d7-af5b4373672d.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Greek Islands Winery Hotels Tonight [Feb 6 - Feb 7](https://www.expedia.ca/Hotel-Search?regionId=6271742&startDate=2026-02-06&endDate=2026-02-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 7 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6271742&startDate=2026-02-07&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6271742&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6271742&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Greek Islands hotels with winery ![Premium Room Caldera View with Outdoor Mini Plunge Pool Double | Balcony](https://images.trvl-media.com/lodging/2000000/1390000/1380900/1380881/dba784a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room Caldera View with Outdoor Mini Plunge Pool Double](https://images.trvl-media.com/lodging/2000000/1390000/1380900/1380881/031618ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/2000000/1390000/1380900/1380881/e316b28b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rocabella Suite Caldera View with Outdoor Mini Plunge Pool for 6 Guests](https://images.trvl-media.com/lodging/2000000/1390000/1380900/1380881/4b2fd998.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rocabella Santorini Hotel & SPA [](https://www.expedia.ca/Santorini-Hotels-Rocabella-Santorini-Hotel-SPA.h1380881.Hotel-Information) Santorini 9.4/10 Exceptional (638 reviews) "Balcony offered a nice view :)" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher Andrew CA $114 CA $134 total includes taxes & fees Feb 13 - Feb 14 [](https://www.expedia.ca/Santorini-Hotels-Rocabella-Santorini-Hotel-SPA.h1380881.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89770000/89767000/89766945/9c033abb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite | Terrace/patio](https://images.trvl-media.com/lodging/90000000/89770000/89767000/89766945/d5bff33f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89770000/89767000/89766945/f5778c8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite](https://images.trvl-media.com/lodging/90000000/89770000/89767000/89766945/246cdada.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mythical Coast Wellness Retreat [](https://www.expedia.ca/Lesvos-Hotels-Mythical-Coast-Wellness-Retreat.h89766945.Hotel-Information) Lesvos 8.6/10 Excellent (47 reviews) "Brand new hotel, lovely staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy [](https://www.expedia.ca/Lesvos-Hotels-Mythical-Coast-Wellness-Retreat.h89766945.Hotel-Information) ![Superior Apartment, 3 Bedrooms, Terrace | Living area](https://images.trvl-media.com/lodging/84000000/83180000/83170300/83170213/8ab55ec9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83180000/83170300/83170213/c1a40c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Apartment, 3 Bedrooms, Terrace](https://images.trvl-media.com/lodging/84000000/83180000/83170300/83170213/df0b43b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Studio Suite, Terrace](https://images.trvl-media.com/lodging/84000000/83180000/83170300/83170213/29d13d9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Elements Cave Suites [](https://www.expedia.ca/Santorini-Hotels-Elements-Suites.h83170213.Hotel-Information) Santorini 9.2/10 Wonderful (16 reviews) "Lovely place to stay in a quiet area that still has great restaurants and some shops around. " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Kyle Schulz CA $146 CA $167 total includes taxes & fees Feb 26 - Feb 27 [](https://www.expedia.ca/Santorini-Hotels-Elements-Suites.h83170213.Hotel-Information) ![Outdoor pool, open 9:30 AM to 7:30 PM, sun loungers](https://images.trvl-media.com/lodging/7000000/6840000/6839300/6839252/cca15556.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Villa, 2 Bedrooms, Private Pool, Vineyard View](https://images.trvl-media.com/lodging/7000000/6840000/6839300/6839252/eb6419c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; Mediterranean cuisine, ocean views ](https://images.trvl-media.com/lodging/7000000/6840000/6839300/6839252/29bd552a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6840000/6839300/6839252/e2793b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### De Sol Spa Hotel [](https://www.expedia.ca/Santorini-Hotels-De-Sol-Spa-Hotel.h6839252.Hotel-Information) Santorini 9.4/10 Exceptional (529 reviews) "The rooms were clean and the service outstanding. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Teresa CA $236 CA $275 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/Santorini-Hotels-De-Sol-Spa-Hotel.h6839252.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1260000/1259500/1259477/5241c8c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/2000000/1260000/1259500/1259477/fa0e4112.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1260000/1259500/1259477/b3cbfa5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1260000/1259500/1259477/1d415748.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Halepa Hotel [](https://www.expedia.ca/Chania-Hotels-Halepa-Hotel.h1259477.Hotel-Information) Halepa 9.0/10 Wonderful (362 reviews) "Friendly staff, great location, good breakfast buffet. Would recommend." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) stacey [](https://www.expedia.ca/Chania-Hotels-Halepa-Hotel.h1259477.Hotel-Information) ![Premium Suite, Balcony | Room amenity](https://images.trvl-media.com/lodging/96000000/95960000/95952500/95952496/b0818739.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, Balcony | Room amenity](https://images.trvl-media.com/lodging/96000000/95960000/95952500/95952496/26506c42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Suite, Hot Tub](https://images.trvl-media.com/lodging/96000000/95960000/95952500/95952496/7ed01e0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/96000000/95960000/95952500/95952496/b79b6120.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Legato Spa Suites [](https://www.expedia.ca/Naxos-Hotels-Naxos.h95952496.Hotel-Information) Naxos 10/10 Exceptional (24 reviews) "First time in Greece and it was one of the best places i’ve stayed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rosa CA $240 CA $274 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/Naxos-Hotels-Naxos.h95952496.Hotel-Information) ![Suite (Polymneia) | Beach/ocean view](https://images.trvl-media.com/lodging/19000000/18170000/18164500/18164486/d61fb9b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Polymneia) | Outdoor spa tub](https://images.trvl-media.com/lodging/19000000/18170000/18164500/18164486/4dffe149.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Melpomeni)](https://images.trvl-media.com/lodging/19000000/18170000/18164500/18164486/4113842e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa (Thaleia) | View from room](https://images.trvl-media.com/lodging/19000000/18170000/18164500/18164486/b0590b52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mykonos Moussa Suites [](https://www.expedia.ca/Mykonos-Hotels-Mykonos-Moussa-Suites.h18164486.Hotel-Information) Mykonos 9.8/10 Exceptional (97 reviews) "Great hospitality. Great sea view. Close to nice beaches. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Osman CA $148 CA $170 total includes taxes & fees Mar 9 - Mar 10 [](https://www.expedia.ca/Mykonos-Hotels-Mykonos-Moussa-Suites.h18164486.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/77000000/76230000/76224500/76224483/ed0c3fd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, Sea View & Outdoor Hot Tub | View from room](https://images.trvl-media.com/lodging/77000000/76230000/76224500/76224483/87c95800.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Suite, Sea View & Outdoor Hot Tub | Living area](https://images.trvl-media.com/lodging/77000000/76230000/76224500/76224483/w3366h2242x0y0-ea28fad2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aelia Suite, Sea View & Outdoor Hot Tub | Terrace/patio](https://images.trvl-media.com/lodging/77000000/76230000/76224500/76224483/b11620ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aelia Luxury Suites [](https://www.expedia.ca/Santorini-Hotels-Aelia-Luxury-Suites.h76224483.Hotel-Information) Santorini 8.8/10 Excellent (16 reviews) "We really had nice stay during our trip to beautiful Santorini! " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Lobsang [](https://www.expedia.ca/Santorini-Hotels-Aelia-Luxury-Suites.h76224483.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/52000000/51270000/51260300/51260204/b2d922b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Suite, Sea View](https://images.trvl-media.com/lodging/52000000/51270000/51260300/51260204/7e188c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite, Sea View (Split Level)](https://images.trvl-media.com/lodging/52000000/51270000/51260300/51260204/438cd1be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, minibar, in-room safe](https://images.trvl-media.com/lodging/52000000/51270000/51260300/51260204/7aa64699.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Phaos Santorini Suites [](https://www.expedia.ca/Santorini-Hotels-Rhapsody-Apartments.h51260204.Hotel-Information) Santorini 9.0/10 Wonderful (222 reviews) "Beautiful stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $60 CA $69 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/Santorini-Hotels-Rhapsody-Apartments.h51260204.Hotel-Information) ![2 outdoor pools](https://images.trvl-media.com/lodging/75000000/74680000/74674700/74674614/434aad3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/75000000/74680000/74674700/74674614/25c01526.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74680000/74674700/74674614/dad6be51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74680000/74674700/74674614/1c2fc141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Manili Boutique Suites & Villas [](https://www.expedia.ca/Archanes-Asterousia-Hotels-Manili-Boutique-Suites-Villas.h74674614.Hotel-Information) Archanes-Asterousia 9.6/10 Exceptional (27 reviews) "Exceptional accommodations in a truly destination village. Great staff, pools everywhere and architecturally a treat! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $173 CA $200 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/Archanes-Asterousia-Hotels-Manili-Boutique-Suites-Villas.h74674614.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=2026-02-20&endDate=2026-02-21®ionId=6271742&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Greek Islands Hotel Reviews ![Rocabella Santorini Hotel & SPA ](https://images.trvl-media.com/lodging/2000000/1390000/1380900/1380881/15e57ee3_y.jpg) ### Rocabella Santorini Hotel & SPA 10/10 Excellent "Balcony offered a nice view :)" [](https://expedia.ca/Santorini-Hotels-Rocabella-Santorini-Hotel-SPA.h1380881.Hotel-Information) ![Ira Hotel & Spa - Adults Only](https://images.trvl-media.com/lodging/7000000/6120000/6116900/6116875/c1b6b3c6_y.jpg) ### Ira Hotel & Spa - Adults Only 10/10 Excellent "The staffs are great . Clean is room and quiet . Amenities are great . The view in the hotel is stunning and amazing . Recommended ! Thank you Kostas for your great service . Maria and Tim " [](https://expedia.ca/Santorini-Hotels-Ira-Hotel-Spa.h6116875.Hotel-Information) ![Hotel Sunny Villas](https://images.trvl-media.com/lodging/2000000/1100000/1095700/1095677/1e5cde74_y.jpg) ### Hotel Sunny Villas 10/10 Excellent "Beautiful stay in Santorini!" [](https://expedia.ca/Santorini-Hotels-Hotel-Sunny-Villas.h1095677.Hotel-Information) ![Volcano View Hotel Santorini](https://images.trvl-media.com/lodging/2000000/1080000/1071600/1071551/a63cc6f8_y.jpg) ### Volcano View Hotel Santorini 10/10 Excellent "Excellent views and a good room with decent amenities. " [](https://expedia.ca/Santorini-Hotels-Volcano-View-Hotel-Santorini.h1071551.Hotel-Information) ![Nefeli Homes - Adults Only](https://images.trvl-media.com/lodging/3000000/2910000/2909000/2908974/c271ee0e_y.jpg) ### Nefeli Homes - Adults Only 10/10 Excellent "Nefeli homes was the best stay we had in Santorini. Our room had the best view and the views from the hotel pool is also amazing! It was super comfortable, spacious, had the friendliest staff who helped us with our every need. I highly recommend this place and would love to stay here again in the future" [](https://expedia.ca/Santorini-Hotels-Nefeli-Homes.h2908974.Hotel-Information)