Title: Book the Best Greek Islands WINERY Hotels in 2025 | 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)[Things to do in Greek Islands](https://expedia.ca/Things-To-Do-In-Greek-Islands.d6271742.Travel-Guide-Activities)[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) # Find Winery Hotels in Greek Islands from CA $81 - ![](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 [Nov 29 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6271742&startDate=2025-11-29&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 30 - Dec 1](https://www.expedia.ca/Hotel-Search?regionId=6271742&startDate=2025-11-30&endDate=2025-12-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6271742&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6271742&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Greek Islands Winery Hotels ![Minibar, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/75000000/74680000/74674700/74674614/aed20882.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with satellite channels, TV, printers](https://images.trvl-media.com/lodging/75000000/74680000/74674700/74674614/62116de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa | Private kitchen](https://images.trvl-media.com/lodging/75000000/74680000/74674700/74674614/4185b415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/75000000/74680000/74674700/74674614/1ceeec6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Manili Boutique Suites & Villas Archanes-Asterousia 9.6/10 Exceptional (27) "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 $241 CA $277 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Archanes-Asterousia-Hotels-Manili-Boutique-Suites-Villas.h74674614.Hotel-Information) ![Suite (Polymneia) | Terrace/patio](https://images.trvl-media.com/lodging/19000000/18170000/18164500/18164486/c6f5bf08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa (Thaleia) | Balcony](https://images.trvl-media.com/lodging/19000000/18170000/18164500/18164486/12ef71fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/19000000/18170000/18164500/18164486/69c38432.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Polymneia) | View from room](https://images.trvl-media.com/lodging/19000000/18170000/18164500/18164486/539c0539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mykonos Moussa Suites Mykonos 9.8/10 Exceptional (94) "Great hospitality. Great sea view. Close to nice beaches. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Osman CA $158 CA $181 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Mykonos-Hotels-Mykonos-Moussa-Suites.h18164486.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/90000000/89770000/89767000/89766945/3d640bb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/90000000/89770000/89767000/89766945/a863e526.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![70-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/90000000/89770000/89767000/89766945/db28ecfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite](https://images.trvl-media.com/lodging/90000000/89770000/89767000/89766945/3912090f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mythical Coast Wellness Retreat Lesvos 8.6/10 Excellent (46) "I booked a junior suite. The description does not match the room. The room was to have a balcony and it does not. It was a basic room of 30 square metres with two single beds pushed together and a chair and small table. The service was terrible. The person at teh front desk in the morning was rude and basically could not wait to get me out. This was out of character witht he wonderful hospitality elsewhere on the island. I would NEVER recommend this place. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Alissa [](https://www.expedia.ca/Lesvos-Hotels-Mythical-Coast-Wellness-Retreat.h89766945.Hotel-Information) ![3 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1390000/1380900/1380881/15e57ee3.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) ![Executive Room Caldera View with Outdoor Mini Plunge Pool Double](https://images.trvl-media.com/lodging/2000000/1390000/1380900/1380881/8f29bed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rocabella Santorini Hotel & SPA Santorini 9.4/10 Exceptional (637) "Excellent hotel location and friendly staff,good service. we love it. Hope we could come back.again in near future." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Fei CA $231 CA $267 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Santorini-Hotels-Rocabella-Santorini-Hotel-SPA.h1380881.Hotel-Information) ![Premier Suite, Hot Tub, Sea View](https://images.trvl-media.com/lodging/52000000/51270000/51260300/51260204/26426d15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Suite, Hot Tub, Sea View](https://images.trvl-media.com/lodging/52000000/51270000/51260300/51260204/d8c8f002.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) ![Exterior](https://images.trvl-media.com/lodging/52000000/51270000/51260300/51260204/88813a1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Phaos Santorini Suites Santorini 9.2/10 Wonderful (216) "Beautiful stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $71 CA $81 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Santorini-Hotels-Rhapsody-Apartments.h51260204.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/24000000/23570000/23567000/23566946/69c15898.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cave Suite Indoor Hot Tub Shared Balcony](https://images.trvl-media.com/lodging/24000000/23570000/23567000/23566946/e24007e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cozy Suite Outdoor Hot Tub Caldera View | View from room](https://images.trvl-media.com/lodging/24000000/23570000/23567000/23566946/90c09315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Suite Outdoor Hot Tub Caldera View](https://images.trvl-media.com/lodging/24000000/23570000/23567000/23566946/8286f22b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aperto Suites - Adults Only Santorini 9.2/10 Wonderful (74) "Staff was very helpful, the room is so nice and the view is fantastic " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Ricardo CA $219 CA $251 total includes taxes & fees Dec 5 - Dec 6 [](https://www.expedia.ca/Santorini-Hotels-Aperto-Suites-Adults-Only.h23566946.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) ![V.I.P. Suite Sea View | Living area](https://images.trvl-media.com/lodging/77000000/76230000/76224500/76224483/ebc8a3c8.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) ![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) ### Aelia Luxury Suites Santorini 8.8/10 Excellent (16) "We really had nice stay during our trip to beautiful Santorini! " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Lobsang CA $145 CA $166 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Santorini-Hotels-Aelia-Luxury-Suites.h76224483.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1260000/1259500/1259477/c01760a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1260000/1259500/1259477/0693740c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1260000/1259500/1259477/d0ba175f.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 Halepa 9.0/10 Wonderful (362) "Quiet location but easily walkable" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Claude CA $108 CA $123 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Chania-Hotels-Halepa-Hotel.h1259477.Hotel-Information) ![Elite Villa, 2 Bedrooms, Hot Tub, Sea View | Terrace/patio](https://images.trvl-media.com/lodging/118000000/117130000/117126700/117126687/79589fb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, Hot Tub, Sea View](https://images.trvl-media.com/lodging/118000000/117130000/117126700/117126687/d9795ce6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, Hot Tub, Sea View | Terrace/patio](https://images.trvl-media.com/lodging/118000000/117130000/117126700/117126687/0dacbe9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, Sea View](https://images.trvl-media.com/lodging/118000000/117130000/117126700/117126687/7fc24136.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Three Domes Oia - an Iconic Collection Oía 9.4/10 Exceptional (14) "Beautiful views great pool and location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Naisi CA $235 CA $269 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Santorini-Hotels-Three-Domes-Oia-An-Iconic-Collection.h117126687.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/3000000/2520000/2511100/2511078/e1b548e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/3000000/2520000/2511100/2511078/354256eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/3000000/2520000/2511100/2511078/4cda4fb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2520000/2511100/2511078/fbaf780f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Strada Marina Zakynthos 8.2/10 Very good (305) "Nice hotel in great location with lovely roof top bar and dining " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Barry [](https://www.expedia.ca/Zakynthos-Hotels-Hotel-Strada-Marina.h2511078.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=2025-12-13&endDate=2025-12-14®ionId=6271742&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_6271742) ## Top Greek Islands Hotel Reviews ![Athina Luxury Suites](https://images.trvl-media.com/lodging/2000000/1850000/1841600/1841546/d25e88d8_y.jpg) ### Athina Luxury Suites 10/10 Excellent "The entire experience was amazing. " [](https://expedia.ca/Santorini-Hotels-Athina-Luxury-Suites.h1841546.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 "Nice vi" [](https://expedia.ca/Santorini-Hotels-Ira-Hotel-Spa.h6116875.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 "The view is magnificent and the staff were absolutely incredible!" [](https://expedia.ca/Santorini-Hotels-Volcano-View-Hotel-Santorini.h1071551.Hotel-Information) ![Astro Palace Hotel & Spa](https://images.trvl-media.com/lodging/4000000/3630000/3625800/3625705/9bed4f63_y.jpg) ### Astro Palace Hotel & Spa 10/10 Excellent "My husband and I stayed at this hotel with our 3-month-old baby for 2 nights — and immediately wished we had booked a longer stay. From the moment we arrived, the staff went above and beyond to make us feel welcome. We've travelled a lot around the world, but the reception team here truly stood out as the most friendly, helpful, and accommodating we've ever encountered. They made travelling with a young baby remarkably easy and we were so grateful. We booked a Senior Suite with an outdoor terrace and private jacuzzi — and it was absolutely perfect. The space was beautiful, and we loved having the jacuzzi to relax in. The pool area was peaceful with comfortable sun loungers, and breakfast each morning was a lovely experience, made even better by the attentive and kind staff. We also really appreciated the location — just an 8-minute uphill walk to the centre of Fira. Overall, we had a fantastic stay and would highly recommend this hotel to anyone visiting Fira." [](https://expedia.ca/Santorini-Hotels-Astro-Palace-Hotel-Spa.h3625705.Hotel-Information) ![Aqua Luxury Suites](https://images.trvl-media.com/lodging/3000000/2840000/2835800/2835751/0f3496e8_y.jpg) ### Aqua Luxury Suites 10/10 Excellent "Oskana and Elena were absolutely great. They offered good advice and made everything very simple. It was a delight staying here. Only regret was we didn't stay longer. The ocean view was unmatched and at the same time it allowed an amazing back drop of the city. " [](https://expedia.ca/Santorini-Hotels-Aqua-Luxury-Suites.h2835751.Hotel-Information)