Title: Book the Best Cyclades Islands WINERY Hotels in 2026 | Expedia.ca [Cyclades Islands Travel Guide](https://expedia.ca/Cyclades-Islands.dx6051353)[Hotels in Cyclades Islands](https://expedia.ca/Cyclades-Islands-Hotels.d6051353.Travel-Guide-Hotels)[Vacation Rentals in Cyclades Islands](https://expedia.ca/Cyclades-Islands-Vacation-Rentals.d6051353.Travel-Guide-VacationRentals)[Flights to Cyclades Islands](https://expedia.ca/Cheap-Flights-To-Cyclades-Islands.d6051353.Travel-Guide-Flights)[Cyclades Islands Car Rentals](https://expedia.ca/Car-Rentals-In-Cyclades-Islands.d6051353.Car-Rental-Guide)[Cyclades Islands Vacation Packages](https://expedia.ca/Cyclades-Islands.d6051353.Destination-Travel-Guides) ![Oia featuring a coastal town and a luxury hotel or resort](https://images.trvl-media.com/place/6051970/d6d7c83d-2485-4cdd-aedf-ad3614820b31.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Cyclades Islands from CA $72 - ![](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 Cyclades Islands Winery Hotels Tonight [Dec 17 - Dec 18](https://www.expedia.ca/Hotel-Search?regionId=6051353&startDate=2025-12-17&endDate=2025-12-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 18 - Dec 19](https://www.expedia.ca/Hotel-Search?regionId=6051353&startDate=2025-12-18&endDate=2025-12-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6051353&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6051353&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Cyclades Islands hotels with winery ![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) ![Exterior](https://images.trvl-media.com/lodging/52000000/51270000/51260300/51260204/88813a1a.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/e0c63620.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) ### Phaos Santorini Suites [](https://www.expedia.ca/Santorini-Hotels-Rhapsody-Apartments.h51260204.Hotel-Information) Santorini 9.2/10 Wonderful (217) "Beautiful stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $62 CA $72 total includes taxes & fees Jan 10 - Jan 11, 2026 [](https://www.expedia.ca/Santorini-Hotels-Rhapsody-Apartments.h51260204.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) ![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) ![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) ![Suite (Polymneia) | Terrace/patio](https://images.trvl-media.com/lodging/19000000/18170000/18164500/18164486/e50128da.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 (94) "Great hospitality. Great sea view. Close to nice beaches. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Osman CA $156 CA $179 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Mykonos-Hotels-Mykonos-Moussa-Suites.h18164486.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83180000/83170300/83170213/d09fc2fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Apartment, 3 Bedrooms, Terrace | Living area](https://images.trvl-media.com/lodging/84000000/83180000/83170300/83170213/84afcb2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, 2 Bedrooms, Terrace | Living area](https://images.trvl-media.com/lodging/84000000/83180000/83170300/83170213/5e30398a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Studio Suite, Terrace | Living area](https://images.trvl-media.com/lodging/84000000/83180000/83170300/83170213/908066c9.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) "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 $94 CA $108 total includes taxes & fees Jan 11 - Jan 12, 2026 [](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/7000000/6840000/6839300/6839252/6cec4f19.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/d152041a.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) ![Bar (on property)](https://images.trvl-media.com/lodging/7000000/6840000/6839300/6839252/4299c5c6.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 (524) "Clean rooms and great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amir [](https://www.expedia.ca/Santorini-Hotels-De-Sol-Spa-Hotel.h6839252.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) ![Deluxe Room Caldera View Double](https://images.trvl-media.com/lodging/2000000/1390000/1380900/1380881/95d03721.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 (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 $260 CA $300 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Santorini-Hotels-Rocabella-Santorini-Hotel-SPA.h1380881.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1850000/1841600/1841550/95fabce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1850000/1841600/1841550/72c411f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1850000/1841600/1841550/e319f3f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, Jetted Tub (Caldera View)](https://images.trvl-media.com/lodging/2000000/1850000/1841600/1841550/1ab51373.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nefeles Luxury Suites [](https://www.expedia.ca/Santorini-Hotels-Nefeles-Luxury-Suites.h1841550.Hotel-Information) Santorini 9.6/10 Exceptional (163) "Panos the manager was amazing & very attentive. The view was amazing & breakfast was delicious. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sydney [](https://www.expedia.ca/Santorini-Hotels-Nefeles-Luxury-Suites.h1841550.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/890000/889500/889455/39a35fad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/890000/889500/889455/513a4b5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/1000000/890000/889500/889455/4a581f06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Triple Room, Sea View | Living area](https://images.trvl-media.com/lodging/1000000/890000/889500/889455/d0cd358c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Theoxenia Caldera Hotel [](https://www.expedia.ca/Santorini-Hotels-Theoxenia-Boutique-Hotel.h889455.Hotel-Information) Santorini 9.2/10 Wonderful (267) "The hotel staff were fantastic in helping us with luggage up the staircase. We had a comfortable stay in a great spot. " ![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg) Anthony [](https://www.expedia.ca/Santorini-Hotels-Theoxenia-Boutique-Hotel.h889455.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) ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/118000000/117130000/117126700/117126687/a28d18f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Three Domes Oia - an Iconic Collection [](https://www.expedia.ca/Santorini-Hotels-Three-Domes-Oia-An-Iconic-Collection.h117126687.Hotel-Information) 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 $249 CA $285 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Santorini-Hotels-Three-Domes-Oia-An-Iconic-Collection.h117126687.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) ![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) ![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) ![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) ### Aperto Suites - Adults Only [](https://www.expedia.ca/Santorini-Hotels-Aperto-Suites-Adults-Only.h23566946.Hotel-Information) 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 [](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) ![Reception](https://images.trvl-media.com/lodging/77000000/76230000/76224500/76224483/a1fd0d5e.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) ![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 Luxury Suites [](https://www.expedia.ca/Santorini-Hotels-Aelia-Luxury-Suites.h76224483.Hotel-Information) 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 [](https://www.expedia.ca/Santorini-Hotels-Aelia-Luxury-Suites.h76224483.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=2025-12-31&endDate=2026-01-01®ionId=6051353&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Cyclades 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 staff was very helpful and friendly. " [](https://expedia.ca/Santorini-Hotels-Athina-Luxury-Suites.h1841546.Hotel-Information) ![Merovigliosso Apartments](https://images.trvl-media.com/lodging/3000000/2810000/2806300/2806230/8c4dfa70_y.jpg) ### Merovigliosso Apartments 10/10 Excellent "The only bus stop at Imerovigli was confusing and not label that caused us missing the bus for Fira. As infrequent as the bus schedule was in November, we were thankful being picked up by a wandering taxi to give us ride to Oia (30 Euro) and then Oia to Fira (30 Euro) which in my opinion much preferred in a tight schedule. The hotel offered me courtesy drop-off at the airport which was super nice of Kostas." [](https://expedia.ca/Santorini-Hotels-Merovigliosso-Apartments.h2806230.Hotel-Information) ![Above Blue Suites](https://images.trvl-media.com/lodging/3000000/2490000/2482700/2482632/78716c47_y.jpg) ### Above Blue Suites 10/10 Excellent "Our experience at Above Blue Suites was incredible. Everything was spotless, and the views were absolutely breathtaking. The breakfast was delicious and full of flavor we genuinely looked forward to it every morning. We loved being able to choose what we wanted and having it delivered right to our room. The staff was very kind, attentive, and professional. I have nothing but wonderful things to say and highly recommend booking your stay with them." [](https://expedia.ca/Santorini-Hotels-Above-Blue-Suites.h2482632.Hotel-Information) ![Hotel Sunny Villas](https://images.trvl-media.com/lodging/2000000/1100000/1095700/1095677/1e5cde74_y.jpg) ### Hotel Sunny Villas 10/10 Excellent "The staff was incredible and the view was so beautiful. The people in Santorini were all so very kind. I would love to go back in the future" [](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) ![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) ![Grand View](https://images.trvl-media.com/lodging/5000000/4540000/4531000/4530928/79060094_y.jpg) ### Grand View 10/10 Excellent "Excellent " [](https://expedia.ca/Santorini-Hotels-Grand-View.h4530928.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) ![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." 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