Title: Book the Best San Juan Island WINERY Hotels in 2025 | Expedia.ca [San Juan Island Travel Guide](https://expedia.ca/San-Juan-Island.dx6054490)[Hotels in San Juan Island](https://expedia.ca/San-Juan-Island-Hotels.d6054490.Travel-Guide-Hotels)[Vacation Rentals in San Juan Island](https://expedia.ca/San-Juan-Island-Vacation-Rentals.d6054490.Travel-Guide-VacationRentals)[Flights to San Juan Island](https://expedia.ca/Cheap-Flights-To-San-Juan-Island.d6054490.Travel-Guide-Flights)[Things to do in San Juan Island](https://expedia.ca/Things-To-Do-In-San-Juan-Island.d6054490.Travel-Guide-Activities)[San Juan Island Car Rentals](https://expedia.ca/Car-Rentals-In-San-Juan-Island.d6054490.Car-Rental-Guide)[San Juan Island Vacation Packages](https://expedia.ca/San-Juan-Island.d6054490.Destination-Travel-Guides) ![San Juan Island which includes island views and boating](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/47000/47801-Friday-Harbor.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in San Juan Island, WA ![](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 San Juan Island Winery Hotels Tonight [Oct 28 - Oct 29](https://www.expedia.ca/Hotel-Search?regionId=6054490&startDate=2025-10-28&endDate=2025-10-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=6054490&startDate=2025-10-29&endDate=2025-10-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6054490&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6054490&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top San Juan Island Winery Hotels ![Front of property](https://images.trvl-media.com/lodging/2000000/1190000/1189800/1189744/4322486e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cafe](https://images.trvl-media.com/lodging/2000000/1190000/1189800/1189744/ce853ab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1190000/1189800/1189744/98210912.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1190000/1189800/1189744/b805211e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Friday Harbor Suites Friday Harbor 8.4/10 Very good (1001) "Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matt CA $244 CA $271 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Friday-Harbor-Hotels-Friday-Harbor-Suites.h1189744.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/1000000/920000/913700/913611/2aa3eb52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/920000/913700/913611/f2fc8111.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/920000/913700/913611/9f8458ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Single Room](https://images.trvl-media.com/lodging/1000000/920000/913700/913611/34bbd966.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bird Rock Hotel Friday Harbor 8.8/10 Excellent (362) "Having stayed at Bird Rock and Earthbox I'd choose Earthbox for my next visit to Friday Harbor. Both properties are well decorated and maintained but, despite Bird Rock's convenience, for those who are walking from the ferry, Earthbox has the advantage of being a quiet location who's rooms ( or at least my room ) have sleeping areas that are not flooded with light ( during typical sleeping hours). The staff are very helpful and welcoming." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tara CA $215 CA $238 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Friday-Harbor-Hotels-Bird-Rock-Hotel.h913611.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22120000/22119500/22119448/a5575aa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/23000000/22120000/22119500/22119448/d95a8a4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/23000000/22120000/22119500/22119448/877337b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/23000000/22120000/22119500/22119448/0b19fda9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1 Bedroom, Sleeps 6 Steps From the Friday Harbor San Juan Island Ferry, Washington Friday Harbor 9.8/10 Exceptional (40) "Perfect place in the perfect location. This is the second time we have stayed here and it was wonderful again. I especially appreciate the quick communication with the host. Thank you!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alex S. CA $393 CA $490 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Friday-Harbor-Hotels-1-Bedroom.h22119448.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945851/0a2d5e81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![ROOM SIX | View from room](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945851/02c6a41f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![ROOM FOUR](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945851/d6db59a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![ROOM TEN](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945851/d1a1b275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Edenwild Boutique Inn Lopez Island 9.4/10 Exceptional (258) "This place is cute and quaint, and the location is perfect - walkable to everything in the main "village" area. The rooms are unique (I peaked inside a few) and homey, and there are many lovely common areas such as outdoor seating and a wraparound porch. It was calm and quiet despite being fully booked, and when we did run into other guests it felt like we were all friends staying together. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hadassah CA $163 CA $180 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Lopez-Island-Hotels-The-Edenwild-Boutique-Inn.h11945851.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1780000/1778200/1778184/f15428c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1780000/1778200/1778184/a86d5778.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1780000/1778200/1778184/fc54fab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1780000/1778200/1778184/c6ac3083.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Suites Oak Harbor by IHG Oak Harbor 9.2/10 Wonderful (605) "Great checkin and excellent room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda CA $162 CA $180 total includes taxes & fees Nov 14 - Nov 15 [](https://www.expedia.ca/Oak-Harbor-Hotels-Candlewood-Suites-Oak-Harbor.h1778184.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109390000/109388900/109388863/eb9d51de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/110000000/109390000/109388900/109388863/w1537h1046x23y0-6cccf977.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109390000/109388900/109388863/71e4c0a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/110000000/109390000/109388900/109388863/27dfd407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3BR Ocean View Farmhouse - 1 min walk to prime west-facing beach! Eastsound CA $375 CA $527 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Eastsound-Hotels-3BR-Ocean-View-Farmhouse-1-Min-Walk-To-Prime-West-Facing-Beach.h109388863.Hotel-Information) ![TV, books, stereo](https://images.trvl-media.com/lodging/61000000/60530000/60528300/60528238/ce3f51a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/61000000/60530000/60528300/60528238/2f78e17d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books, stereo](https://images.trvl-media.com/lodging/61000000/60530000/60528300/60528238/fab47866.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books, stereo](https://images.trvl-media.com/lodging/61000000/60530000/60528300/60528238/f82fd3eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Light-filled home with fenced yard - two dogs welcome - walk everywhere Anacortes 9.2/10 Wonderful (61) "The house was perfect for our family" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janice M. CA $175 CA $552 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Anacortes-Hotels-Light-Filled-Home-With-Fenced-Yard-Two-Dogs-Welcome-Walk-Everywhere.h60528238.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/76000000/75230000/75221900/75221819/9f0db9bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/76000000/75230000/75221900/75221819/499b3ad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75230000/75221900/75221819/7acf5b96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/76000000/75230000/75221900/75221819/950e6061.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dog-friendly wood cabin with full kitchen & free WiFi near the water Eastsound 7.6/10 Good (50) "I only utilized the downstairs bed and it was comfortable. I cooked most of my meals. The location, for me, was wonderful: in an old forest. Lovely! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dr. Susan CA $111 CA $352 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Eastsound-Hotels-Dog-Friendly-Wood-Cabin-With-Full-Kitchen-Free-WiFi-Near-The-Water.h75221819.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95960000/95959800/95959751/ecb188b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/96000000/95960000/95959800/95959751/2468ed25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95960000/95959800/95959751/4560ebcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/96000000/95960000/95959800/95959751/bade1f19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lux Coastal Retreat & Hot Tub Oak Harbor 9.8/10 Exceptional (12) "Beautiful views, cozy place & close to local shopping. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shelley R. CA $350 CA $691 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Oak-Harbor-Hotels-Lux-Coastal-Retreat-Hot-Tub.h95959751.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59960000/59957200/59957124/74b9780c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/60000000/59960000/59957200/59957124/827baf22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59960000/59957200/59957124/7ff48104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/60000000/59960000/59957200/59957124/9e3e5cbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern, dog-friendly cabin with fast WiFi, washer/dryer, deck & forest views Eastsound 9.4/10 Exceptional (67) "We loved the forest views and the home was very clean and comfortable. The location was very convenient, close to town and water. Highly recommend for a stay on Orcas." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Annie T. CA $112 CA $497 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Eastsound-Hotels-Modern.h59957124.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. 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