Title: Book the Best Oia WINERY Hotels in 2025 | Expedia.ca [Oia Travel Guide](https://expedia.ca/Oia.dx6051970)[Hotels in Oia](https://expedia.ca/Oia-Hotels.d6051970.Travel-Guide-Hotels)[Vacation Rentals in Oia](https://expedia.ca/Oia-Vacation-Rentals.d6051970.Travel-Guide-VacationRentals)[Flights to Oia](https://expedia.ca/Cheap-Flights-To-Oia.d6051970.Travel-Guide-Flights)[Things to do in Oia](https://expedia.ca/Things-To-Do-In-Oia.d6051970.Travel-Guide-Activities)[Oia Car Rentals](https://expedia.ca/Car-Rentals-In-Oia.d6051970.Car-Rental-Guide)[Oia Vacation Packages](https://expedia.ca/Oia.d6051970.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/408000/408515-Greece.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Oia from CA $124 ![](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 Oia Winery Hotels Tonight [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=6051970&startDate=2025-10-15&endDate=2025-10-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=6051970&startDate=2025-10-16&endDate=2025-10-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6051970&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6051970&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Oia Winery Hotels ![Deluxe Seaview Suite | View from room](https://images.trvl-media.com/lodging/70000000/69870000/69860900/69860857/97143da9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Pool Suite](https://images.trvl-media.com/lodging/70000000/69870000/69860900/69860857/7a91dd92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9:30 AM to 8:00 PM, sun loungers](https://images.trvl-media.com/lodging/70000000/69870000/69860900/69860857/103f1776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cave House Suite](https://images.trvl-media.com/lodging/70000000/69870000/69860900/69860857/a918ccac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Museum Project Oia Santorini 9.6/10 Exceptional (157) "Loved this stay" CA $148 CA $172 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Santorini-Hotels-The-Museum-Project-Oia.h69860857.Hotel-Information) ![Blue Horizon Villa, outdoor Plunge Pool | Terrace/patio](https://images.trvl-media.com/lodging/6000000/5190000/5182700/5182628/e4ae9aca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, Jetted Tub, Sea View (Full Moon Villa Outdoor Plunge Pool) | Jetted tub](https://images.trvl-media.com/lodging/6000000/5190000/5182700/5182628/42e59343.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5190000/5182700/5182628/e68c6f0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, Jetted Tub, Sea View (Full Moon Villa Outdoor Plunge Pool) | Living room](https://images.trvl-media.com/lodging/6000000/5190000/5182700/5182628/5fcde07a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### White Pearl Villas Santorini 9.6/10 Exceptional (185) "The property staff were so kind and helpful" CA $234 CA $269 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Santorini-Hotels-White-Pearl-Villas.h5182628.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/16000000/15110000/15106000/15105908/97dcf9b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, premium bedding, in-room safe, individually decorated](https://images.trvl-media.com/lodging/16000000/15110000/15106000/15105908/55bf2584.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, premium bedding, in-room safe, individually decorated](https://images.trvl-media.com/lodging/16000000/15110000/15106000/15105908/f0b61dd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Villa, 2 Bedrooms, Private Pool, Sea View | Jetted tub](https://images.trvl-media.com/lodging/16000000/15110000/15106000/15105908/c1de0bd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ode Villa Santorini 9.4/10 Exceptional (50) "Beautiful Villa with everything you need to make your stay comfortable. Breakfast was delicious, homemade and well balanced. The pool was amazing and so clean. Absolutely loved everything about our stay. Both Vicky and Salvatore made us feel so welcomed. " CA $335 CA $384 total includes taxes & fees Oct 25 - Oct 26 [](https://www.expedia.ca/Santorini-Hotels-Ode-Villa.h15105908.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) ![Exterior](https://images.trvl-media.com/lodging/118000000/117130000/117126700/117126687/a28d18f4.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) ### Three Domes Oia - an Iconic Collection Oía 9.2/10 Wonderful (12) "Beautiful views great pool and location " CA $379 CA $432 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Santorini-Hotels-Three-Domes-Oia-An-Iconic-Collection.h117126687.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95540000/95538400/95538374/49a4e0dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite](https://images.trvl-media.com/lodging/96000000/95540000/95538400/95538374/dc66474b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment | Breakfast meal](https://images.trvl-media.com/lodging/96000000/95540000/95538400/95538374/139ea4de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite](https://images.trvl-media.com/lodging/96000000/95540000/95538400/95538374/5b460d3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Alegria by Casa Sigalas Santorini 9.4/10 Exceptional (12) "Wow … amazing hosts… amazing room .. amazing facilities .. great location .. an amazing first 3 days of our Greece island hopping tour " CA $152 CA $176 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Santorini-Hotels-Alegria-By-Casa-Sigalas.h95538374.Hotel-Information) ![Deluxe Villa, 2 Bedrooms, Jetted Tub (Athiri) | View from room](https://images.trvl-media.com/lodging/16000000/15650000/15649400/15649388/f740c70d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Villa, 2 Bedrooms, Jetted Tub (Nykteri) | Living room](https://images.trvl-media.com/lodging/16000000/15650000/15649400/15649388/9eb510f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Villa, 2 Bedrooms, Jetted Tub (Vinsanto) | Terrace/patio](https://images.trvl-media.com/lodging/16000000/15650000/15649400/15649388/9f3ee963.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Villa, Jetted Tub (Mezzo)](https://images.trvl-media.com/lodging/16000000/15650000/15649400/15649388/389d7c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vino Houses Santorini 9.8/10 Exceptional (40) "The hostess and the while staff was very friendly and helpful in arranging rental car and other reservations. The place was clean and breakfast was good too. I highly recommend this place." CA $235 CA $275 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Santorini-Hotels-Vino-Houses.h15649388.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/16000000/15630000/15620500/15620437/11a61ebc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15630000/15620500/15620437/f28c9966.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Duplex](https://images.trvl-media.com/lodging/16000000/15630000/15620500/15620437/df86e1b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/16000000/15630000/15620500/15620437/ff2d9057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Paradisos Oia Santorini 8.8/10 Excellent (49) "The service was excellent, everything was clean, peaceful, and it was a very family-friendly hotel. It was a cosy stay." CA $106 CA $124 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Santorini-Hotels-Paradisos-Oia.h15620437.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76410000/76407700/76407664/23617756.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/77000000/76410000/76407700/76407664/05533c6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/77000000/76410000/76407700/76407664/79bb7a0e_edited_1295.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76410000/76407700/76407664/492d57cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TRADITIONAL CAVE in the heart of old OIA Santorini 10/10 Exceptional (11) "Overall just an amazing experience! It was a wonderful place to stay, the view was amazing, and anything that we needed help with (luggage/transfer around island) the owners were so quick to help out!" CA $179 CA $272 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Santorini-Hotels-Sunset-CAVE-In-The-Heart-Of-OIA.h76407664.Hotel-Information) ![Romantic Suite, 1 Bedroom, Jetted Tub (Panoramic View)](https://images.trvl-media.com/lodging/21000000/20490000/20486900/20486868/6c49b866.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Suite, 1 Bedroom, Jetted Tub (Panoramic View)](https://images.trvl-media.com/lodging/21000000/20490000/20486900/20486868/4bbac8e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor/outdoor pool](https://images.trvl-media.com/lodging/21000000/20490000/20486900/20486868/e2978fd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Suite, 1 Bedroom, Jetted Tub (Panoramic View) | Living area](https://images.trvl-media.com/lodging/21000000/20490000/20486900/20486868/b4d09d6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lava Caves Santorini 10/10 Exceptional (11) "Great host, very nice views, breakfast is amazing." CA $493 CA $568 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Santorini-Hotels-Lava-Caves.h20486868.Hotel-Information) ![Panoramic Villa | Balcony view](https://images.trvl-media.com/lodging/68000000/67420000/67418500/67418442/9e87ff5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Villa](https://images.trvl-media.com/lodging/68000000/67420000/67418500/67418442/5da36429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/68000000/67420000/67418500/67418442/9a44fe01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Villa](https://images.trvl-media.com/lodging/68000000/67420000/67418500/67418442/b1874703.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sophia Privilege Santorini 10/10 Exceptional (11) "Best location in Oia. " CA $521 CA $616 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Santorini-Hotels-Sophia-Privilege.h67418442.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=2025-10-28&endDate=2025-10-29®ionId=6051970&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Oia Hotel Reviews ![Anemomilos Hotel & Apartments](//images.trvl-media.com/lodging/5000000/4100000/4099700/4099689/d369d593_y.jpg) ### Anemomilos Hotel & Apartments 10/10 Excellent "Todo excelente en especial Lenna hizo que nuestra estancia se sintiera como en casa. 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[Hotels with an Indoor Pool in Santorini](https://www.expedia.ca/Santorini-Hotels-Hotels-With-Indoor-Pool.0-0-d177970-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in Santorini](https://www.expedia.ca/Santorini-Hotels-Hotels-With-Smoking-Rooms.0-0-d177970-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Lake Hotels in Santorini](https://www.expedia.ca/Santorini-Hotels-Lake-Hotels.0-0-d177970-tLakeHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Santorini](https://www.expedia.ca/Santorini-Hotels-Pet-Friendly-Hotel.0-0-d177970-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Santorini](https://www.expedia.ca/Santorini-Hotels-Shopping-Hotel.0-0-d177970-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Ski Hotels in Santorini](https://www.expedia.ca/Santorini-Hotels-Ski-Hotel.0-0-d177970-tSkiHotel.Travel-Guide-Filter-Hotels) - [Hotels near Skaros Rock](https://www.expedia.ca/Skaros-Rock-Hotels.0-l6323759-0.Travel-Guide-Filter-Hotels) - [Therasia Hotels](https://www.expedia.ca/Therasia-Hotels.d6320746.Travel-Guide-Hotels) - [Tholos Hotels](https://www.expedia.ca/Tholos-Hotels.d6359663.Travel-Guide-Hotels) - [Vourvoulos Hotels](https://www.expedia.ca/Vourvoulos-Hotels.d6035032.Travel-Guide-Hotels) - [Flights to Imerovigli](https://www.expedia.ca/Cheap-Flights-To-Imerovigli.d6051972.Travel-Guide-Flights) - [Flights to Therasia](https://www.expedia.ca/Cheap-Flights-To-Therasia.d6320746.Travel-Guide-Flights) - [Flights to Vourvoulos](https://www.expedia.ca/Cheap-Flights-To-Vourvoulos.d6035032.Travel-Guide-Flights) - [Flights from Amoudi Bay](https://www.expedia.ca/lp/flights/6324292/flights-from-amoudi-bay) - [Amoudi Bay](https://www.expedia.ca/Amoudi-Bay-South-Aegean.d553248635026737110.Vacation-Attraction) - [Visit Amoudi Bay](https://www.expedia.ca/Amoudi-Bay.dx6324292) - [Byzantine Castle Ruins](https://www.expedia.ca/Byzantine-Castle-Ruins-Santorini.d553248621532502148.Vacation-Attraction) - [Dominican Convent](https://www.expedia.ca/Dominican-Convent-Santorini.d6062281.Vacation-Attraction) - [Visit Fira](https://www.expedia.ca/Fira.dx6051971) - [Firostefani Vacations](https://www.expedia.ca/Firostefani.d6342055.Destination-Travel-Guides) - [Imerovigli Vacations](https://www.expedia.ca/Imerovigli.d6051972.Destination-Travel-Guides) - [Visit Imerovigli](https://www.expedia.ca/Imerovigli.dx6051972) - [Visit Koloumpos](https://www.expedia.ca/Koloumpos.dx855580624558641152) - [Oia Blue Dome Church Viewpoint](https://www.expedia.ca/Oia-Blue-Dome-Church-Viewpoint-Santorini.d553248635919605513.Vacation-Attraction) - [Oia Castle](https://www.expedia.ca/Oia-Castle-Santorini.d6165890.Vacation-Attraction) - [Visit Ormos Armenis](https://www.expedia.ca/Ormos-Armenis.dx855580816909426688) - [Visit Panagia Kalou](https://www.expedia.ca/Panagia-Kalou.dx855580416869294080) - [Visit Paradisos](https://www.expedia.ca/Paradisos.dx855581720263942144) - [Petros M. Nomikos Conference Centre](https://www.expedia.ca/Petros-M-Nomikos-Conference-Centre-Santorini.d6062305.Vacation-Attraction) - [Skaros Rock](https://www.expedia.ca/Skaros-Rock-Santorini.d6323759.Vacation-Attraction) - [Visit Therasia](https://www.expedia.ca/Therasia.dx6320746) - [Visit Tholos](https://www.expedia.ca/Tholos.dx6359663) - [Visit Vourvoulos](https://www.expedia.ca/Vourvoulos.dx6035032) - [Avis Rental Cars in Imerovigli](https://www.expedia.ca/Avis-Car-Rentals-In-Imerovigli.d6051972-c41.Car-Rental-Guide-Suppliers) - [Buchbinder Germany Rental Cars in Imerovigli](https://www.expedia.ca/Buchbinder-Germany-Car-Rentals-In-Imerovigli.d6051972-c1053.Car-Rental-Guide-Suppliers) - [Budget Canaries Rental Cars in Imerovigli](https://www.expedia.ca/Budget-Canaries-Car-Rentals-In-Imerovigli.d6051972-c1136.Car-Rental-Guide-Suppliers) - [Car rental Imerovigli](https://www.expedia.ca/Car-Rentals-In-Imerovigli.d6051972.Car-Rental-Guide) - [Centauro Rental Cars in Imerovigli](https://www.expedia.ca/Centauro-Car-Rentals-In-Imerovigli.d6051972-c1015.Car-Rental-Guide-Suppliers) - [Goldcar Key’n Go Rental Cars in Imerovigli](https://www.expedia.ca/Goldcar-Keyn-Go-Car-Rentals-In-Imerovigli.d6051972-c1044.Car-Rental-Guide-Suppliers) - [Record Rent A Car Rental Cars in Imerovigli](https://www.expedia.ca/Record-Rent-A-Car-Car-Rentals-In-Imerovigli.d6051972-c30.Car-Rental-Guide-Suppliers) - [Imerovigli Vacation Rentals](https://www.expedia.ca/Imerovigli-Vacation-Rentals.d6051972.Travel-Guide-VacationRentals) - [Ormos Armenis Vacation Rentals](https://www.expedia.ca/Ormos-Armenis-Vacation-Rentals.d855580816909426688.Travel-Guide-VacationRentals) - [Panagia Kalou Vacation Rentals](https://www.expedia.ca/Panagia-Kalou-Vacation-Rentals.d855580416869294080.Travel-Guide-VacationRentals) - [Paradisos Vacation Rentals](https://www.expedia.ca/Paradisos-Vacation-Rentals.d855581720263942144.Travel-Guide-VacationRentals) - [Things to do in Amoudi Bay](https://www.expedia.ca/Things-To-Do-In-Amoudi-Bay.d6324292.Travel-Guide-Activities) - [Things to do in Firostefani](https://www.expedia.ca/Things-To-Do-In-Firostefani.d6342055.Travel-Guide-Activities) - [Things to do in Imerovigli](https://www.expedia.ca/Things-To-Do-In-Imerovigli.d6051972.Travel-Guide-Activities) - [Things to do in Therasia](https://www.expedia.ca/Things-To-Do-In-Therasia.d6320746.Travel-Guide-Activities)