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&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)

## Explore a world of travel with Expedia

-   Lodging
-   Flights
-   Packages
-   Cars
-   Vacation Rental
-   Other

-   [4 Star Hotels in Sao Roque do Pico](https://www.expedia.ca/4Star-Sao-Roque-Do-Pico-Hotels.s40-0-d6133974.Travel-Guide-Filter-Hotels)
-   [Baixa Hotels](https://www.expedia.ca/Baixa-Hotels.d553248635975857630.Travel-Guide-Hotels)
-   [Bandeiras Hotels](https://www.expedia.ca/Bandeiras-Hotels.d3000021686.Travel-Guide-Hotels)
-   [Cabo Branco Hotels](https://www.expedia.ca/Cabo-Branco-Hotels.d553248635975862504.Travel-Guide-Hotels)
-   [Cais do Pico Hotels](https://www.expedia.ca/Cais-Do-Pico-Hotels.d553248635975870685.Travel-Guide-Hotels)
-   [Calhau Hotels](https://www.expedia.ca/Calhau-Hotels.d3000021634.Travel-Guide-Hotels)
-   [Calheta de Nesquim Hotels](https://www.expedia.ca/Calheta-De-Nesquim-Hotels.d3000021632.Travel-Guide-Hotels)
-   [Beach Hotel Hotels in Faial Island](https://www.expedia.ca/Faial-Island-Hotels-Beach-Hotel.0-0-d6051141-tBeachHotel.Travel-Guide-Filter-Hotels)
-   [Cheap Hotels in Faial Island](https://www.expedia.ca/Faial-Island-Hotels-Cheap-Hotels.0-0-d6051141-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [Hotels & Resorts for Couples in Faial Island](https://www.expedia.ca/Faial-Island-Hotels-Couples-Resorts-Hotels.0-0-d6051141-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)
-   [Historic Hotels in Faial Island](https://www.expedia.ca/Faial-Island-Hotels-Historic-Hotel.0-0-d6051141-tHistoricHotel.Travel-Guide-Filter-Hotels)
-   [Hotels with Free Breakfast in Faial Island](https://www.expedia.ca/Faial-Island-Hotels-Hotels-With-Free-Breakfast.0-0-d6051141-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels)
-   [Luxury Hotels in Faial Island](https://www.expedia.ca/Faial-Island-Hotels-Luxury-Hotel.0-0-d6051141-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Oceanfront Hotels in Faial Island](https://www.expedia.ca/Faial-Island-Hotels-Oceanfront-Hotels.0-0-d6051141-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
-   [Pet-Friendly Hotels in Faial Island](https://www.expedia.ca/Faial-Island-Hotels-Pet-Friendly-Hotel.0-0-d6051141-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
-   [Hotel Wedding Venues Hotels in Faial Island](https://www.expedia.ca/Faial-Island-Hotels-Wedding-Hotels.0-0-d6051141-tWeddingHotels.Travel-Guide-Filter-Hotels)
-   [Lgbt Friendly Hotels in Horta](https://www.expedia.ca/Horta-Hotels-LGBT-Friendly-Hotel.0-0-d1500-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels)
-   [Luxury Hotels in Horta](https://www.expedia.ca/Horta-Hotels-Luxury-Hotel.0-0-d1500-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Horta Hotels](https://www.expedia.ca/Horta-Hotels.d1500.Travel-Guide-Hotels)
-   [Pousadas in Horta](https://www.expedia.ca/Horta-Pousadas.d1500-aaPousadas.Travel-Guide-Accommodation)
-   [Lgbt Friendly Hotels in Lajes do Pico](https://www.expedia.ca/Lajes-Do-Pico-Hotels-LGBT-Friendly-Hotel.0-0-d6159823-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels)
-   [Lajes do Pico Hotels](https://www.expedia.ca/Lajes-Do-Pico-Hotels.d6159823.Travel-Guide-Hotels)
-   [Madalena Hotels](https://www.expedia.ca/Madalena-Hotels.d6144445.Travel-Guide-Hotels)
-   [Monte Hotels](https://www.expedia.ca/Monte-Hotels.d6263538.Travel-Guide-Hotels)
-   [Hotels near Pico Island](https://www.expedia.ca/Pico-Island-Airport-Hotels.0-aPIX-0.Travel-Guide-Filter-Hotels)
-   [Piedade Hotels](https://www.expedia.ca/Piedade-Hotels.d3000398590.Travel-Guide-Hotels)
-   [Pontas Negras Hotels](https://www.expedia.ca/Pontas-Negras-Hotels.d6324554.Travel-Guide-Hotels)
-   [Santo Amaro Hotels](https://www.expedia.ca/Santo-Amaro-Hotels.d6134067.Travel-Guide-Hotels)
-   [São Caetano Hotels](https://www.expedia.ca/Sao-Caetano-Hotels.d553248635975865560.Travel-Guide-Hotels)
-   [São João Hotels](https://www.expedia.ca/Sao-Joao-Hotels.d553248635975854738.Travel-Guide-Hotels)
-   [Hotels near Sao Jorge Island](https://www.expedia.ca/Sao-Jorge-Island-Airport-Hotels.0-aSJZ-0.Travel-Guide-Filter-Hotels)
-   [Beach Hotel Hotels in São Jorge Island](https://www.expedia.ca/Sao-Jorge-Island-Hotels-Beach-Hotel.0-0-d3182-tBeachHotel.Travel-Guide-Filter-Hotels)
-   [Business Hotels in São Jorge Island](https://www.expedia.ca/Sao-Jorge-Island-Hotels-Business-Hotel.0-0-d3182-tBusinessHotel.Travel-Guide-Filter-Hotels)
-   [Cheap Hotels in São Jorge Island](https://www.expedia.ca/Sao-Jorge-Island-Hotels-Cheap-Hotels.0-0-d3182-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [Hotels & Resorts for Couples in São Jorge Island](https://www.expedia.ca/Sao-Jorge-Island-Hotels-Couples-Resorts-Hotels.0-0-d3182-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)
-   [Family Hotels in São Jorge Island](https://www.expedia.ca/Sao-Jorge-Island-Hotels-Family-Hotel.0-0-d3182-tFamilyHotel.Travel-Guide-Filter-Hotels)
-   [Historic Hotels in São Jorge Island](https://www.expedia.ca/Sao-Jorge-Island-Hotels-Historic-Hotel.0-0-d3182-tHistoricHotel.Travel-Guide-Filter-Hotels)
-   [Hotels with Balconies in São Jorge Island](https://www.expedia.ca/Sao-Jorge-Island-Hotels-Hotels-With-Balconies.0-0-d3182-tHotelswithBalconies.Travel-Guide-Filter-Hotels)
-   [Luxury Hotels in São Jorge Island](https://www.expedia.ca/Sao-Jorge-Island-Hotels-Luxury-Hotel.0-0-d3182-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Pet-Friendly Hotels in São Jorge Island](https://www.expedia.ca/Sao-Jorge-Island-Hotels-Pet-Friendly-Hotel.0-0-d3182-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
-   [Spa Hotels in São Jorge Island](https://www.expedia.ca/Sao-Jorge-Island-Hotels-Spa-Hotel.0-0-d3182-tSpaHotel.Travel-Guide-Filter-Hotels)
-   [Hotel Wedding Venues Hotels in São Jorge Island](https://www.expedia.ca/Sao-Jorge-Island-Hotels-Wedding-Hotels.0-0-d3182-tWeddingHotels.Travel-Guide-Filter-Hotels)
-   [Winery Hotels in São Jorge Island](https://www.expedia.ca/Sao-Jorge-Island-Hotels-Winery-Hotel.0-0-d3182-tWineryHotel.Travel-Guide-Filter-Hotels)
-   [Lgbt Friendly Hotels in Sao Mateus](https://www.expedia.ca/Sao-Mateus-Hotels-LGBT-Friendly-Hotel.0-0-d6348415-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels)
-   [Sao Mateus Hotels](https://www.expedia.ca/Sao-Mateus-Hotels.d6348415.Travel-Guide-Hotels)
-   [São Miguel Arcanjo Hotels](https://www.expedia.ca/Sao-Miguel-Arcanjo-Hotels.d553248635975869997.Travel-Guide-Hotels)
-   [Lgbt Friendly Hotels in Sao Roque do Pico](https://www.expedia.ca/Sao-Roque-Do-Pico-Hotels-LGBT-Friendly-Hotel.0-0-d6133974-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels)
-   [Sao Roque do Pico Hotels](https://www.expedia.ca/Sao-Roque-Do-Pico-Hotels.d6133974.Travel-Guide-Hotels)
-   [Terra do Pão Hotels](https://www.expedia.ca/Terra-Do-Pao-Hotels.d3000020926.Travel-Guide-Hotels)
-   [Urzelina Hotels](https://www.expedia.ca/Urzelina-Hotels.d3000020900.Travel-Guide-Hotels)
-   [Velas Hotels](https://www.expedia.ca/Velas-Hotels.d182256.Travel-Guide-Hotels)

-   [Flights to Horta](https://www.expedia.ca/Cheap-Flights-To-Horta.d1500.Travel-Guide-Flights)
-   [Flights to Madalena](https://www.expedia.ca/Cheap-Flights-To-Madalena.d6144445.Travel-Guide-Flights)
-   [Flights to Sao Jorge Island](https://www.expedia.ca/Cheap-Flights-To-Sao-Jorge-Island.d6024902.Travel-Guide-Flights)
-   [Flights from Horta](https://www.expedia.ca/lp/flights/1500/flights-from-horta)
-   [Flights from Velas](https://www.expedia.ca/lp/flights/182256/flights-from-velas)
-   [Flights from Madalena](https://www.expedia.ca/lp/flights/6144445/flights-from-madalena)
-   [Flights from Lajes do Pico](https://www.expedia.ca/lp/flights/6159823/flights-from-lajes-do-pico)
-   [Flights from Calheta](https://www.expedia.ca/lp/flights/6345213/flights-from-calheta)
-   [Flights from Lisbon (LIS) to Pico Island (PIX)](https://www.expedia.ca/lp/flights/lis/pix/lisbon-to-pico-island)
-   [Flights from Lisbon (LIS) to Sao Jorge Island (SJZ)](https://www.expedia.ca/lp/flights/lis/sjz/lisbon-to-sao-jorge-island)
-   [Flights from Ponta Delgada (PDL) to Pico Island (PIX)](https://www.expedia.ca/lp/flights/pdl/pix/ponta-delgada-to-pico-island)
-   [Flights from Ponta Delgada (PDL) to Sao Jorge Island (SJZ)](https://www.expedia.ca/lp/flights/pdl/sjz/ponta-delgada-to-sao-jorge-island)
-   [Flights from Pristina (PRN) to Pico Island (PIX)](https://www.expedia.ca/lp/flights/prn/pix/pristina-to-pico-island)
-   [Flights from San Jose (SJC) to Pico Island (PIX)](https://www.expedia.ca/lp/flights/sjc/pix/san-jose-to-pico-island)
-   [Flights from Ottawa (YOW) to Pico Island (PIX)](https://www.expedia.ca/lp/flights/yow/pix/ottawa-to-pico-island)
-   [Flights from Montreal (YUL) to Pico Island (PIX)](https://www.expedia.ca/lp/flights/yul/pix/montreal-to-pico-island)
-   [Flights from Montreal (YUL) to Sao Jorge Island (SJZ)](https://www.expedia.ca/lp/flights/yul/sjz/montreal-to-sao-jorge-island)
-   [Flights from Vancouver (YVR) to Pico Island (PIX)](https://www.expedia.ca/lp/flights/yvr/pix/vancouver-to-pico-island)
-   [Flights from Vancouver (YVR) to Sao Jorge Island (SJZ)](https://www.expedia.ca/lp/flights/yvr/sjz/vancouver-to-sao-jorge-island)
-   [Flights from Winnipeg (YWG) to Pico Island (PIX)](https://www.expedia.ca/lp/flights/ywg/pix/winnipeg-to-pico-island)
-   [Flights from Winnipeg (YWG) to Sao Jorge Island (SJZ)](https://www.expedia.ca/lp/flights/ywg/sjz/winnipeg-to-sao-jorge-island)
-   [Flights from Calgary (YYC) to Pico Island (PIX)](https://www.expedia.ca/lp/flights/yyc/pix/calgary-to-pico-island)
-   [Flights from Toronto (YYZ) to Pico Island (PIX)](https://www.expedia.ca/lp/flights/yyz/pix/toronto-to-pico-island)
-   [Flights from Toronto (YYZ) to Sao Jorge Island (SJZ)](https://www.expedia.ca/lp/flights/yyz/sjz/toronto-to-sao-jorge-island)

-   [Visit Bandeiras](https://www.expedia.ca/Bandeiras.dx3000021686)
-   [Lajes do Pico Vacations](https://www.expedia.ca/Lajes-Do-Pico.d6159823.Destination-Travel-Guides)
-   [Visit Lajes do Pico](https://www.expedia.ca/Lajes-Do-Pico.dx6159823)
-   [Visit Madalena](https://www.expedia.ca/Madalena.dx6144445)
-   [Visit Manadas](https://www.expedia.ca/Manadas.dx553248635975858340)
-   [Visit Pontas Negras](https://www.expedia.ca/Pontas-Negras.dx6324554)
-   [Visit Sao Mateus](https://www.expedia.ca/Sao-Mateus.dx6348415)
-   [Visit São Miguel Arcanjo](https://www.expedia.ca/Sao-Miguel-Arcanjo.dx553248635975869997)

-   [Car rental Horta](https://www.expedia.ca/Car-Rentals-In-Horta.d1500.Car-Rental-Guide)
-   [Car rental Lajes do Pico](https://www.expedia.ca/Car-Rentals-In-Lajes-Do-Pico.d6159823.Car-Rental-Guide)
-   [Car rental Madalena](https://www.expedia.ca/Car-Rentals-In-Madalena.d6144445.Car-Rental-Guide)
-   [Rental cars Pico Island airport](https://www.expedia.ca/Car-Rentals-In-Pico-Island.d6024786.Car-Rental-Guide)
-   [Rental cars Sao Jorge Island airport](https://www.expedia.ca/Car-Rentals-In-Sao-Jorge-Island.d6024902.Car-Rental-Guide)
-   [Car rental Sao Roque do Pico](https://www.expedia.ca/Car-Rentals-In-Sao-Roque-Do-Pico.d6133974.Car-Rental-Guide)
-   [Car rental Velas](https://www.expedia.ca/Car-Rentals-In-Velas.d182256.Car-Rental-Guide)

-   [Calheta de Nesquim Vacation Rentals](https://www.expedia.ca/Calheta-De-Nesquim-Vacation-Rentals.d3000021632.Travel-Guide-VacationRentals)
-   [Horta Vacation Rentals](https://www.expedia.ca/Horta-Vacation-Rentals.d1500.Travel-Guide-VacationRentals)
-   [Lajes do Pico Vacation Rentals](https://www.expedia.ca/Lajes-Do-Pico-Vacation-Rentals.d6159823.Travel-Guide-VacationRentals)
-   [Madalena Vacation Rentals](https://www.expedia.ca/Madalena-Vacation-Rentals.d6144445.Travel-Guide-VacationRentals)
-   [Pontas Negras Vacation Rentals](https://www.expedia.ca/Pontas-Negras-Vacation-Rentals.d6324554.Travel-Guide-VacationRentals)
-   [Sao Roque do Pico Vacation Rentals](https://www.expedia.ca/Sao-Roque-Do-Pico-Vacation-Rentals.d6133974.Travel-Guide-VacationRentals)

-   [Things to do in Flamengos](https://www.expedia.ca/Things-To-Do-In-Flamengos.d3000378039.Travel-Guide-Activities)
-   [Things to do in Horta](https://www.expedia.ca/Things-To-Do-In-Horta.d1500.Travel-Guide-Activities)
-   [Things to do in Madalena](https://www.expedia.ca/Things-To-Do-In-Madalena.d6144445.Travel-Guide-Activities)
-   [Things to do in Velas](https://www.expedia.ca/Things-To-Do-In-Velas.d182256.Travel-Guide-Activities)