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)

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# Find Winery Hotels in Pico Island

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## Check availability on Pico Island Winery Hotels

Tonight

[Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=2802&startDate=2025-10-04&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 5 - Oct 6](https://www.expedia.ca/Hotel-Search?regionId=2802&startDate=2025-10-05&endDate=2025-10-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=2802&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[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)

## Top Pico Island Winery Hotels

![TV, fireplace](https://images.trvl-media.com/lodging/109000000/108590000/108586400/108586373/d978f8cc.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)

![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)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108590000/108586400/108586373/769e2dd5.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 $280

CA $383 total

includes taxes & fees

Oct 5 - Oct 6

[](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/d0b6d0d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vila Paim - Apart. Low

São Roque do Pico

CA $74

CA $250 total

includes taxes & fees

Oct 26 - Oct 27

[](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=2025-10-18&endDate=2025-10-19&regionId=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. "

[](https://expedia.ca/Madalena-Hotels-Pocinhobay.h6169076.Hotel-Information)

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