Title: Book the Best Cyclades Islands WINERY Hotels in 2025 | 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) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/37000/37814-Mykonos-Town.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Cyclades 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 Cyclades Islands Winery Hotels Tonight [Sep 29 - Sep 30](https://www.expedia.ca/Hotel-Search?regionId=6051353&startDate=2025-09-29&endDate=2025-09-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 30 - Oct 1](https://www.expedia.ca/Hotel-Search?regionId=6051353&startDate=2025-09-30&endDate=2025-10-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6051353&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6051353&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cyclades Islands Winery Hotels ![Outdoor pool, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/16000000/15750000/15748300/15748288/c8b3c347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/16000000/15750000/15748300/15748288/4371188a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Villa, Private Pool, Sea View](https://images.trvl-media.com/lodging/16000000/15750000/15748300/15748288/32d3cd1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Villa, Private Pool, Sea View | Terrace/patio](https://images.trvl-media.com/lodging/16000000/15750000/15748300/15748288/0ffb6693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Desiterra Resort & Spa Santorini 9.6/10 Exceptional (201) "Amazing, best vacation! " CA $106 CA $145 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Santorini-Hotels-Desiterra-Resort.h15748288.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/880000/874600/874572/ef0d028c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, Private Pool, Sea View](https://images.trvl-media.com/lodging/1000000/880000/874600/874572/53a6804e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gym](https://images.trvl-media.com/lodging/1000000/880000/874600/874572/2322b512.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Suite Outdoor Hot Tub Sea View](https://images.trvl-media.com/lodging/1000000/880000/874600/874572/bbf85f7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Paros Agnanti Resort & Spa Paros 9.2/10 Wonderful (254) "The staff was outstanding!!!" CA $328 CA $398 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Paros-Hotels-Paros-Agnanti-Hotel.h874572.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) ![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 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 Santorini 9.4/10 Exceptional (632) "Hotel was close to a small town (15 minute walk) good restaurants. We also rented a quad and saw the rest of Santorini Oia and Fira with lovely restaurants, shopping and galleries " CA $314 CA $373 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Santorini-Hotels-Rocabella-Santorini-Hotel-SPA.h1380881.Hotel-Information) ![4 outdoor pools](https://images.trvl-media.com/lodging/77000000/76200000/76192400/76192350/d8976689.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/77000000/76200000/76192400/76192350/26bec34c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76200000/76192400/76192350/e32115ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76200000/76192400/76192350/8082770a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sea Breeze Santorini Beach Resort, Curio Collection Hilton Santorini 9.6/10 Exceptional (59) "The service was 5 star" CA $246 CA $304 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Santorini-Hotels-Sea-Breeze-Santorini-Beach-Resort.h76192350.Hotel-Information) ![Private spa tub](https://images.trvl-media.com/lodging/39000000/38260000/38257900/38257893/e7cd1329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Genesis Suite Hot Tub Caldera View](https://images.trvl-media.com/lodging/39000000/38260000/38257900/38257893/b8c3fc87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Phaedra Suite Caldera View](https://images.trvl-media.com/lodging/39000000/38260000/38257900/38257893/93cf00cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Nefeli Suite Hot Tub Caldera View](https://images.trvl-media.com/lodging/39000000/38260000/38257900/38257893/64b7cbba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Symphony Suites Santorini 10/10 Exceptional (207) "Very nice apartment suites and delicious breakfast " CA $145 CA $168 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Santorini-Hotels-Symphony-Suites.h38257893.Hotel-Information) ![Seasonal outdoor pool, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/4000000/3500000/3498200/3498111/4f95b93b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, Garden View, Ground Floor | Garden view](https://images.trvl-media.com/lodging/4000000/3500000/3498200/3498111/6dde60cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, 2 beach bars, poolside bar](https://images.trvl-media.com/lodging/4000000/3500000/3498200/3498111/82d4ea13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, Garden View, Ground Floor](https://images.trvl-media.com/lodging/4000000/3500000/3498200/3498111/aba922a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Saint Andrea Sea Side Resort - Adults Only Paros 9.6/10 Exceptional (147) "Attentive and pleasant staff. Great location to use as home base to explore the rest of the island " CA $261 CA $314 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Paros-Hotels-Saint-Andrea-Sea-Side-Resort.h3498111.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/9000000/8070000/8061500/8061478/95be22d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Sugarmoon, Caldera View) | Living room](https://images.trvl-media.com/lodging/9000000/8070000/8061500/8061478/ea7895e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/9000000/8070000/8061500/8061478/6c026fe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private Unlimited View Suite](https://images.trvl-media.com/lodging/9000000/8070000/8061500/8061478/ea6d543d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Alti Santorini Suites Santorini 9.8/10 Exceptional (129) "The property is wonderful the staff are great and extremely helpful" CA $409 CA $468 total includes taxes & fees Oct 18 - Oct 19 [](https://www.expedia.ca/Santorini-Hotels-Alti-Santorini-Suites.h8061478.Hotel-Information) ![Swim-up bar](https://images.trvl-media.com/lodging/9000000/8750000/8747900/8747816/a8038e93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/9000000/8750000/8747900/8747816/9e65e583.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, minibar, in-room safe, individually decorated](https://images.trvl-media.com/lodging/9000000/8750000/8747900/8747816/d8adb8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/9000000/8750000/8747900/8747816/ed765eb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Zoumis Residence Paros 9.8/10 Exceptional (84) "Convenient and beautiful hotel! " CA $141 CA $164 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Paros-Hotels-Zoumis-Studios.h8747816.Hotel-Information) ![Honeymoon Suite, Private Pool, Sea View with Jacuzzi | Private spa tub](https://images.trvl-media.com/lodging/28000000/27840000/27834400/27834301/b76cf509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun Suite, Sea View | Bathroom](https://images.trvl-media.com/lodging/28000000/27840000/27834400/27834301/601b00b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun Suite, Sea View | Beach/ocean view](https://images.trvl-media.com/lodging/28000000/27840000/27834400/27834301/bb6b8818.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, Sea View | Balcony](https://images.trvl-media.com/lodging/28000000/27840000/27834400/27834301/dae47120.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Summer Senses Luxury Resort Paros 9.4/10 Exceptional (108) "Beautiful modern resort with excellent customer service " CA $335 CA $406 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Paros-Hotels-Summer-Senses-Luxury-Resort.h27834301.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/6000000/5010000/5005600/5005550/92159b9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite (with Plunge Pool) | View from room](https://images.trvl-media.com/lodging/6000000/5010000/5005600/5005550/e8c61f40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite (with Plunge Pool) | Terrace/patio](https://images.trvl-media.com/lodging/6000000/5010000/5005600/5005550/4f3d9b6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach/ocean view](https://images.trvl-media.com/lodging/6000000/5010000/5005600/5005550/1d335051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grace Hotel, Auberge Collection Santorini 9.8/10 Exceptional (130) "View is stunning and the service is exceptional. Everyone was amazingly nice, friendly and helpful. We are definitely coming back to stay again at the Grace." CA $487 CA $610 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Santorini-Hotels-Grace-Hotel-Santorini.h5005550.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=2025-10-13&endDate=2025-10-14®ionId=6051353&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Cyclades Islands Hotel Reviews ![De Sol Spa Hotel](//images.trvl-media.com/lodging/7000000/6840000/6839300/6839252/6cec4f19_y.jpg) ### De Sol Spa Hotel 10/10 Excellent "The hotel is well maintained, our hotel room was great and the reception staff were fantastic. " [](https://expedia.ca/Santorini-Hotels-De-Sol-Spa-Hotel.h6839252.Hotel-Information) ![Hotel Sunny Villas](//images.trvl-media.com/lodging/2000000/1100000/1095700/1095677/1e5cde74_y.jpg) ### Hotel Sunny Villas 10/10 Excellent "The staff was so happy to help with any and all needs . They cared about the people who stayed there and was always willing to listen and support them. " [](https://expedia.ca/Santorini-Hotels-Hotel-Sunny-Villas.h1095677.Hotel-Information) ![The Majestic Hotel](//images.trvl-media.com/lodging/1000000/870000/866200/866124/97f44cce_y.jpg) ### The Majestic Hotel 10/10 Excellent "very nice hotel. Great location and courteous staff. I highly recommend it." [](https://expedia.ca/Santorini-Hotels-The-Majestic-Hotel.h866124.Hotel-Information) ![Absolute Bliss](//images.trvl-media.com/lodging/3000000/2190000/2180400/2180348/9c318ca7_y.jpg) ### Absolute Bliss 10/10 Excellent "Unbelievable views, beautiful and spacious rooms and the staff is absolutely wonderful!! Their response time for any requests or needs was immediate. Highly recommend Absolute Bliss!" [](https://expedia.ca/Santorini-Hotels-Absolute-Bliss.h2180348.Hotel-Information) ![Volcano View Hotel Santorini](//images.trvl-media.com/lodging/2000000/1080000/1071600/1071551/a63cc6f8_y.jpg) ### Volcano View Hotel Santorini 10/10 Excellent "The view speaks for itself. Sunsets are stunning. The staff at this hotel is exceptionally helpful and friendly. Ask the concierge to schedule a tour of Santorini. It is well worth it." [](https://expedia.ca/Santorini-Hotels-Volcano-View-Hotel-Santorini.h1071551.Hotel-Information) ![Ira Hotel & Spa - Adults Only](//images.trvl-media.com/lodging/7000000/6120000/6116900/6116875/c1b6b3c6_y.jpg) ### Ira Hotel & Spa - Adults Only 10/10 Excellent "The Ira did an outstanding job helping us retrieve a suitcase that was accidentally left behind. They went above and beyond to help us get it delivered back to us. In addition to that, the hotel is beautiful! Clean and friendly. The waiter hand delivered an excellent assortment of breakfast foods right to our table. Would stay at this hotel again!" [](https://expedia.ca/Santorini-Hotels-Ira-Hotel-Spa.h6116875.Hotel-Information) ![Above Blue Suites](//images.trvl-media.com/lodging/3000000/2490000/2482700/2482632/78716c47_y.jpg) ### Above Blue Suites 10/10 Excellent "This is a dreamy, better than expected place with views to die for. Since I have never been to Santorini before, it represents the island perfectly while its location works for airport and port transfers. The room is clean, stylish and simply adorable " [](https://expedia.ca/Santorini-Hotels-Above-Blue-Suites.h2482632.Hotel-Information) ![Veggera Hotel](//images.trvl-media.com/lodging/1000000/910000/901900/901870/ad7c0538_y.jpg) ### Veggera Hotel 10/10 Excellent "John at the front desk does an amazing job helping guests with check in and also with suggestions on places to visit." 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