Title: Book the Best San Juan Island WINERY Hotels in 2026 | 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 a bay or harbour, sailing and boating](https://images.trvl-media.com/place/1248/c87f5637-9933-4199-a829-107b6a04e0b2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/1248/c87f5637-9933-4199-a829-107b6a04e0b2.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 San Juan Island Winery Hotels Tonight [Jan 28 - Jan 29](https://www.expedia.ca/Hotel-Search?regionId=6054490&startDate=2026-01-28&endDate=2026-01-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 29 - Jan 30](https://www.expedia.ca/Hotel-Search?regionId=6054490&startDate=2026-01-29&endDate=2026-01-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6054490&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6054490&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for San Juan Island hotels with winery ![Cafe](https://images.trvl-media.com/lodging/2000000/1190000/1189800/1189744/ce853ab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/2000000/1190000/1189800/1189744/7166daf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gift shop](https://images.trvl-media.com/lodging/2000000/1190000/1189800/1189744/f8475bb5.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) ### Friday Harbor Suites [](https://www.expedia.ca/Friday-Harbor-Hotels-Friday-Harbor-Suites.h1189744.Hotel-Information) Friday Harbor 8.4/10 Very good (1,001 reviews) "Great room, great staff, love the hotel. This will be our go to for visits here! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathaniel CA $245 CA $271 total includes taxes & fees Feb 6 - Feb 7 [](https://www.expedia.ca/Friday-Harbor-Hotels-Friday-Harbor-Suites.h1189744.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/1000000/920000/913700/913611/09bdf350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/920000/913700/913611/w2997h1998x0y0-31b84938.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/920000/913700/913611/2aa3eb52.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) ### Bird Rock Hotel [](https://www.expedia.ca/Friday-Harbor-Hotels-Bird-Rock-Hotel.h913611.Hotel-Information) Friday Harbor 8.8/10 Excellent (362 reviews) "The electronic check-in went smoothly and the location was great. Room was comfortable and the area was quiet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bret CA $197 CA $218 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Friday-Harbor-Hotels-Bird-Rock-Hotel.h913611.Hotel-Information) ![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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22120000/22119500/22119448/859fff60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/23000000/22120000/22119500/22119448/877337b7.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 [](https://www.expedia.ca/Friday-Harbor-Hotels-1-Bedroom.h22119448.Hotel-Information) Friday Harbor 9.8/10 Exceptional (42 reviews) "We love the location and design of this house rental. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica F. CA $357 CA $444 total includes taxes & fees Feb 26 - Feb 27 [](https://www.expedia.ca/Friday-Harbor-Hotels-1-Bedroom.h22119448.Hotel-Information) ![Smart TV, fireplace, DVD player, table tennis](https://images.trvl-media.com/lodging/30000000/29620000/29616500/29616490/ded04384.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/30000000/29620000/29616500/29616490/355b9d35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29620000/29616500/29616490/43a90190.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/30000000/29620000/29616500/29616490/0e51e3eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Roche Harbor Bayfront Escape: Luxe Retreat with Kayaks, Deck & Wildlife Views [](https://www.expedia.ca/Friday-Harbor-Hotels-Roche-Harbor-Waterfront-Home-On-Westcott-Bay-Getaway-On-The-Bay.h29616490.Hotel-Information) Friday Harbor 10/10 Exceptional (194 reviews) "This house provided EVERYTHING we needed for our vacation!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica N. CA $428 CA $915 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Friday-Harbor-Hotels-Roche-Harbor-Waterfront-Home-On-Westcott-Bay-Getaway-On-The-Bay.h29616490.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945851/5743edf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![COTTAGE ONE | Garden view](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945851/9bd8f176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![ROOM FIVE | View from room](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945851/012ea966.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 [](https://www.expedia.ca/Lopez-Island-Hotels-The-Edenwild-Boutique-Inn.h11945851.Hotel-Information) Lopez Island 9.4/10 Exceptional (259 reviews) "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 $159 CA $175 total includes taxes & fees Jan 29 - Jan 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/e58a6268.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/2000000/1780000/1778200/1778184/94082a31.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/2000000/1780000/1778200/1778184/4e4bc5b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1780000/1778200/1778184/f15428c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Suites Oak Harbor by IHG [](https://www.expedia.ca/Oak-Harbor-Hotels-Candlewood-Suites-Oak-Harbor.h1778184.Hotel-Information) Oak Harbor 9.2/10 Wonderful (613 reviews) "So very comfortable and quiet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen CA $186 CA $207 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Oak-Harbor-Hotels-Candlewood-Suites-Oak-Harbor.h1778184.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/110000000/109390000/109388900/109388863/8b486d67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/110000000/109390000/109388900/109388863/b122008c.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) ![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! [](https://www.expedia.ca/Eastsound-Hotels-3BR-Ocean-View-Farmhouse-1-Min-Walk-To-Prime-West-Facing-Beach.h109388863.Hotel-Information) Eastsound CA $370 CA $529 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Eastsound-Hotels-3BR-Ocean-View-Farmhouse-1-Min-Walk-To-Prime-West-Facing-Beach.h109388863.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/83000000/82500000/82496600/82496571/40a0f118.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/83000000/82500000/82496600/82496571/a934148c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/83000000/82500000/82496600/82496571/122a10b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/83000000/82500000/82496600/82496571/2bb21817.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deception Pass home with forest and bay views [](https://www.expedia.ca/Oak-Harbor-Hotels-Deception-Pass-Home-With-Forest-And-Bay-Views.h82496571.Hotel-Information) Oak Harbor 10/10 Exceptional (22 reviews) "Beautiful stay with everything we needed and more;) Kind host, close to everything but secluded. Excellent family adventure! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca CA $147 CA $438 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Oak-Harbor-Hotels-Deception-Pass-Home-With-Forest-And-Bay-Views.h82496571.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/36000000/35880000/35873900/35873819/3d1d4cf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Internet, bed sheets](https://images.trvl-media.com/lodging/36000000/35880000/35873900/35873819/c567aaa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/36000000/35880000/35873900/35873819/2581bb25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/36000000/35880000/35873900/35873819/f8380ba8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dog-friendly studio w/ kitchenette, WiFi, yard & fire pit [](https://www.expedia.ca/Eastsound-Hotels-Dog-Friendly-Studio-W-Kitchenette.h35873819.Hotel-Information) Orcas Island 9.2/10 Wonderful (75 reviews) "Peaceful and quiet spot in the woods yet near the Ferry and Lake Killebrew! The owners art is on display. Another wonderful relaxing stay for this return customer." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joshua F. CA $106 CA $365 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Eastsound-Hotels-Dog-Friendly-Studio-W-Kitchenette.h35873819.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106310000/106306100/106306032/02e5eded.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/107000000/106310000/106306100/106306032/bff6ad5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/107000000/106310000/106306100/106306032/08bbb211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106310000/106306100/106306032/2029be29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean/mountain view condo with balcony & lovely location near Moran SP [](https://www.expedia.ca/Eastsound-Hotels-Oceanmountain-View-Condo-With-Balcony-Lovely-Location-Near-Moran-SP.h106306032.Hotel-Information) Eastsound 9.2/10 Wonderful (5 reviews) "Good" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa P. CA $238 CA $588 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Eastsound-Hotels-Oceanmountain-View-Condo-With-Balcony-Lovely-Location-Near-Moran-SP.h106306032.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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