Title: Book the Best Oia WINERY Hotels in 2026 | 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) ![Oia which includes a coastal town and a sunset](https://images.trvl-media.com/place/6051970/e5da4ab9-ff0a-4eb1-97d9-49548b308721.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6051970/e5da4ab9-ff0a-4eb1-97d9-49548b308721.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 Oia Winery Hotels Tonight [Jan 23 - Jan 24](https://www.expedia.ca/Hotel-Search?regionId=6051970&startDate=2026-01-23&endDate=2026-01-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 24 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6051970&startDate=2026-01-24&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6051970&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6051970&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Oia hotels with winery ![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114520000/114517400/114517380/5b88ea9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/115000000/114520000/114517400/114517380/27ce7105.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private spa tub](https://images.trvl-media.com/lodging/115000000/114520000/114517400/114517380/fb55fadf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/115000000/114520000/114517400/114517380/d41331c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Phaos Oia Suites [](https://www.expedia.ca/Santorini-Hotels-Phaos-Oia-Suites.h114517380.Hotel-Information) Santorini 9.6/10 Exceptional (5 reviews) "Very nice " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zohal [](https://www.expedia.ca/Santorini-Hotels-Phaos-Oia-Suites.h114517380.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34390000/34383100/34383012/59f85c80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34390000/34383100/34383012/bf0302fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34390000/34383100/34383012/bf7ba3d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/35000000/34390000/34383100/34383012/98578fa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SantoriniParadise: PARADISE cave house, indoor winery & outdoor hot tub, Caldera [](https://www.expedia.ca/Santorini-Hotels-SantoriniParadise-PARADISE-Cave-House.h34383012.Hotel-Information) santorini 9.8/10 Exceptional (121 reviews) "Location was incredible and the view" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexandra D. CA $291 CA $474 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Santorini-Hotels-SantoriniParadise-PARADISE-Cave-House.h34383012.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34190000/34187400/34187377/762dba0b_edited_28f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34190000/34187400/34187377/51f879a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34190000/34187400/34187377/6b9d720a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/35000000/34190000/34187400/34187377/0bad9df4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SantoriniParadise: HELIOS villa, amazing sunset views, perfect dream vacation! [](https://www.expedia.ca/Santorini-Hotels-SantoriniParadise-HELIOS-Villa.h34187377.Hotel-Information) Oia 9.8/10 Exceptional (61 reviews) "Perfect location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bev C. CA $291 CA $474 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Santorini-Hotels-SantoriniParadise-HELIOS-Villa.h34187377.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33740000/33736200/33736174/d173b521_edited_7935.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33740000/33736200/33736174/0a1b1a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/34000000/33740000/33736200/33736174/482c05cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, music library](https://images.trvl-media.com/lodging/34000000/33740000/33736200/33736174/412976f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SantoriniParadise: BLUE & WHITE cave house, authentic experience, Caldera view [](https://www.expedia.ca/Santorini-Hotels-SantoriniParadise-BLUE-WHITE-Cave-House.h33736174.Hotel-Information) Oia 10/10 Exceptional (86 reviews) "Excellent location, clean and Maria & her team were friendly and professionally. Thank you." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Wan Ching C. CA $242 CA $413 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Santorini-Hotels-SantoriniParadise-BLUE-WHITE-Cave-House.h33736174.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/40000000/39990000/39986300/39986250/0945c4c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/40000000/39990000/39986300/39986250/36181610.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/40000000/39990000/39986300/39986250/a0b01258.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/40000000/39990000/39986300/39986250/b636fdf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oia Mansion 4 Bedroom Villa With Panoramic Sunset View [](https://www.expedia.ca/Santorini-Hotels-Oia-Mansion-4-Bedroom-Villa-With-Panoramic-Sunset-View.h39986250.Hotel-Information) Santorini 9.4/10 Exceptional (3 reviews) "The best place to stay in Oia, the location is perfect! The house is beautiful with lots of historic charm. Lily was also very pleasant and helpful to work with. We will be staying here again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jordan G. CA $879 CA $879 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Santorini-Hotels-Oia-Mansion-4-Bedroom-Villa-With-Panoramic-Sunset-View.h39986250.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/37000000/36970000/36969600/36969587/30e24473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/37000000/36970000/36969600/36969587/0c59d415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/37000000/36970000/36969600/36969587/3e67eb41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36970000/36969600/36969587/1912e328.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aerie beautiful house, heart of Oia's traditional settlement, Caldera view [](https://www.expedia.ca/Santorini-Hotels-Aerie-Beautiful-House.h36969587.Hotel-Information) Οία 9.6/10 Exceptional (52 reviews) "This place is awesome! It’s very well located and the hostesses are very friendly and extremely attentive and helpful. We had all we needed and were very comfortable in our stay. I’d definitely stay there again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gabriel R. CA $727 CA $1,010 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Santorini-Hotels-Aerie-Beautiful-House.h36969587.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/117000000/116580000/116571200/116571151/151609dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116580000/116571200/116571151/b8afa06c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/117000000/116580000/116571200/116571151/71464326.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116580000/116571200/116571151/18e421f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ground Floor | Three-Bedroom Heritage Residence with Jacuzzi and Private Terrace, Villa Oro [](https://www.expedia.ca/Santorini-Hotels-Ground-Floor-Three-Bedroom-Heritage-Residence-With-Jacuzzi-And-Private-Terrace.h116571151.Hotel-Information) Oia CA $1,940 CA $1,940 total includes taxes & fees Jan 24 - Jan 25 [](https://www.expedia.ca/Santorini-Hotels-Ground-Floor-Three-Bedroom-Heritage-Residence-With-Jacuzzi-And-Private-Terrace.h116571151.Hotel-Information) ![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) ![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) ![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 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 $111 CA $131 total includes taxes & fees Jan 24 - Jan 25 [](https://www.expedia.ca/Santorini-Hotels-Rocabella-Santorini-Hotel-SPA.h1380881.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) ![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) ![Premium Suite, Sea View](https://images.trvl-media.com/lodging/52000000/51270000/51260300/51260204/b4c27391.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 (221 reviews) "Beautiful stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $75 CA $86 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Santorini-Hotels-Rhapsody-Apartments.h51260204.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) ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/84000000/83180000/83170300/83170213/c1a40c34.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 $147 CA $168 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Santorini-Hotels-Elements-Suites.h83170213.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=2026-02-06&endDate=2026-02-07®ionId=6051970&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Oia Hotel Reviews ## Frequently asked questions ### How much does a winery hotel in Oia cost? ### Which area of Oia is best to stay in for vineyards and wineries? > Couples eager to embrace the romance of Santorini will find Pyrgos particularly appealing. The village's traditional architecture, winding pathways, and panoramic vistas create a picturesque backdrop for intimate moments. Strolling hand-in-hand through the vineyards at sunset, or enjoying a candlelit dinner at a local taverna, adds a magical touch to any romantic getaway. > > > For families, Pyrgos provides a wonderful blend of adventure and relaxation. With its quieter atmosphere compared to the bustling Oia, families can explore the surrounding countryside on foot or by bike. Engaging vineyard tours often include interactive experiences for children, making it educational and fun. Plus, the nearby beaches are easily reachable, offering opportunities for sun-soaked days. ### What are some great winery hotels in Oia with wine cellars? > The luxurious 5-star Canaves Oia Suites (rated 9.7) and Canaves Epitome (also rated 9.7) are both renowned for their legendary wine cellars, showcasing hundreds of bottles from around the world. They provide curated wine tasting experiences that highlight Santorini's rich winemaking tradition and the unique volcanic soil that produces indigenous grape varieties, making your stay truly immersive. > > > For a more relaxed stay, the Vino Houses in Oia Village offers a delightful winery hotel experience. This property includes free continental breakfast and WiFi, along with a children's pool, making it a great choice for families. It's noted for its proximity to local vineyards and the vibrant wine culture of the area. > > > Additionally, the Azalea Houses and Filotera Suites are excellent options located in or near Oia. Both hotels offer easy access to local wineries and wine tours, along with lovely terraces and gardens that enhance the wine-focused experience. > > > If you're after a stay that combines luxury accommodation with authentic wine cellar experiences, Canaves Oia properties stand out as premier options. ### What winery activities should we do in Oia? > For couples planning a romantic escape, a sunset wine tasting at one of Oia's elegant wineries is an unforgettable experience. Many venues, such as Santo Wines or Domaine Sigalas, provide intimate settings where you can sip exquisite wines while watching the sun dip below the horizon, painting the sky in hues of orange and pink. > > > Families, too, can enjoy the winery experience, as many offer educational tours that engage children with the beauty of nature and the magic of fermentation. Some vineyards have kid-friendly activities, ensuring everyone can participate in the adventure. > > > Additionally, consider joining a guided wine tour that combines visits to several wineries with local delicacies. This option allows for a deep dive into the region's culinary offerings, showcasing how local foods pair perfectly with the wines produced nearby. ### Does Oia host any wine festivals or events? > For couples looking to enhance their romantic getaway, the Santorini Wine Festival is a highlight. Typically held in August, this event showcases local wineries offering tastings of their finest wines paired with delicious traditional cuisine. It's an unforgettable way to experience the island's flavours while enjoying the picturesque backdrop of Oia. > > > Families will also find opportunities to engage in wine culture through family-friendly winery tours. Many vineyards offer educational experiences that include a stroll through the vineyards, insights into the winemaking process, and tastings that can be tailored to all ages, ensuring everyone can enjoy the day. ### How can I save on a winery hotel in Oia with Expedia? ### Is it cheaper to book flights and a winery hotel in Oia as a package deal? ### Can I cancel my winery hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - [4 Star Hotels in Imerovigli ](https://www.expedia.ca/4Star-Imerovigli-Hotels.s40-0-d6051972.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Imerovigli ](https://www.expedia.ca/5Star-Imerovigli-Hotels.s50-0-d6051972.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Akrotiri ](https://www.expedia.ca/Akrotiri-Hotels-Luxury-Hotel.0-0-d6051761-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Amoudi Bay ](https://www.expedia.ca/Amoudi-Bay-Hotels-Beach-Hotel.0-0-d6324292-tBeachHotel.Travel-Guide-Filter-Hotels) - 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