Title: Book the Best Pico Island WINERY Hotels in 2025 | Expedia.ca [Pico Island Travel Guide](https://expedia.ca/Pico-Island.dx2802)[Hotels in Pico Island](https://expedia.ca/Pico-Island-Hotels.d2802.Travel-Guide-Hotels)[Vacation Rentals in Pico Island](https://expedia.ca/Pico-Island-Vacation-Rentals.d2802.Travel-Guide-VacationRentals)[Flights to Pico Island](https://expedia.ca/Cheap-Flights-To-Pico-Island.d2802.Travel-Guide-Flights)[Things to do in Pico Island](https://expedia.ca/Things-To-Do-In-Pico-Island.d2802.Travel-Guide-Activities)[Pico Island Car Rentals](https://expedia.ca/Car-Rentals-In-Pico-Island.d2802.Car-Rental-Guide)[Pico Island Vacation Packages](https://expedia.ca/Pico-Island.d2802.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/ab5c794a1b8908e054bc05015fda3e94.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Pico Island ![](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 Pico Island Winery Hotels Tonight [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=2802&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=2802&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=2802&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=2802&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Pico Island Winery Hotels ![1 bedroom](https://images.trvl-media.com/lodging/49000000/48670000/48667500/48667429/b0aa1996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/49000000/48670000/48667500/48667429/fa624471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/49000000/48670000/48667500/48667429/589b0ff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/49000000/48670000/48667500/48667429/61eb6559.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Very well equipped apartment in the center of São Roque do Pico São Roque do Pico "I stayed in this apartment with my family of 4. The apartment itself was small but ok. Note that the management keeps the remote control for AC and if you need it, they charge a daily fee of 10EUR per day. The communication with the manager has been very difficult since the beginning. I’ve sent a message a month prior to arrival to confirm there was enough room for the 4 of us. I never got any answers. The day before our arrival, I sent another message that was again unanswered. Even VRBO... CA $147 CA $295 total includes taxes & fees Nov 7 - Nov 8 [](https://www.expedia.ca/Sao-Roque-Do-Pico-Hotels-Very-Well-Equipped-Apartment-In-The-Center-Of-SAo-Roque-Do-Pico.h48667429.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/109000000/108590000/108586400/108586373/d978f8cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108590000/108586400/108586373/5cd86bc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108590000/108586400/108586373/08a5e6e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/109000000/108590000/108586400/108586373/2b2f7390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment 'Vista Da Baía - Casa Do Aniceto' with Sea View, Private Terrace and Wi-Fi Santo António SRP CA $277 CA $379 total includes taxes & fees Oct 18 - Oct 19 [](https://www.expedia.ca/Sao-Roque-Do-Pico-Hotels-Apartment-Vista-Da-Baia-Casa-Do-Aniceto-With-Sea-View.h108586373.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/54000000/53940000/53937100/53937027/fad0670b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/54000000/53940000/53937100/53937027/acb54a78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/54000000/53940000/53937100/53937027/9085a24d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/54000000/53940000/53937100/53937027/5ec5ed3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vila Paim - Apart. Low São Roque do Pico CA $73 CA $248 total includes taxes & fees Oct 18 - Oct 19 [](https://www.expedia.ca/Sao-Roque-Do-Pico-Hotels-Vila-Paim-Apart-Low.h53937027.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=2025-10-29&endDate=2025-10-30®ionId=2802&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Pico Island Hotel Reviews ![Hotel Caravelas](//images.trvl-media.com/lodging/5000000/4350000/4349900/4349893/b6eac151_y.jpg) ### Hotel Caravelas 10/10 Excellent "A one night stay only to catch a flight. Hotel was clean, comfortable and staff were friendly and efficient. Breakfast buffet was busy but comprehensive. " [](https://expedia.ca/Madalena-Hotels-Hotel-Caravelas.h4349893.Hotel-Information) ![Pocinhobay](//images.trvl-media.com/lodging/7000000/6170000/6169100/6169076/eae42dc7_y.jpg) ### Pocinhobay 10/10 Excellent "A gem of a property - close enough to everything but far enough to enjoy the peacefulness of the island. Staff were helpful, polite, courteous and thoughtful. Highly recommend. 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