Title: Book the Best Portland WINERY Hotels in 2026 | Expedia.ca [Hotels in Portland](https://expedia.ca/Portland-Hotels.d6338411.Travel-Guide-Hotels)[Vacation Rentals in Portland](https://expedia.ca/Portland-Vacation-Rentals.d6338411.Travel-Guide-VacationRentals)[Portland Car Rentals](https://expedia.ca/Car-Rentals-In-Portland.d6338411.Car-Rental-Guide)[Portland Vacation Packages](https://expedia.ca/Portland.d6338411.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/winery.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Portland, WI from CA $116 - ![](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 Portland Winery Hotels Tonight [Jan 1 - Jan 2](https://www.expedia.ca/Hotel-Search?regionId=6338411&startDate=2026-01-01&endDate=2026-01-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 2 - Jan 3](https://www.expedia.ca/Hotel-Search?regionId=6338411&startDate=2026-01-02&endDate=2026-01-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6338411&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6338411&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Portland hotels with winery ![Front of property](https://images.trvl-media.com/lodging/1000000/50000/43200/43135/2e6a1c41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/50000/43200/43135/77780605.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/43200/43135/3bbecd3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/50000/43200/43135/6760a9f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spark by Hilton La Crosse Onalaska [](https://www.expedia.ca/Onalaska-Hotels-Stay-Suites.h43135.Hotel-Information) Onalaska 8.4/10 Very good (90) "The staff was extremely helpful and courteous. The room was comfortable with a large shower area. I would definitely stay here agin" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin CA $100 CA $116 total includes taxes & fees Jan 16 - Jan 17 [](https://www.expedia.ca/Onalaska-Hotels-Stay-Suites.h43135.Hotel-Information) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/79000000/78340000/78334800/78334776/c6bc30ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/79000000/78340000/78334800/78334776/8588471d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78340000/78334800/78334776/c231f4c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78340000/78334800/78334776/97977cd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quaint cabin overlooking the creek below and wetlands in the valley basin. [](https://www.expedia.ca/Norwalk-Hotels-Cozy-Retreat-Nuzzled-In-Wisconsins-Forested-Ridges-And-Spring-Fed-Creek-Bottoms.h78334776.Hotel-Information) Norwalk 10/10 Exceptional (22) "Beautiful cabin 100% recommend good communication " ![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg) anayeli CA $333 CA $402 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/Norwalk-Hotels-Cozy-Retreat-Nuzzled-In-Wisconsins-Forested-Ridges-And-Spring-Fed-Creek-Bottoms.h78334776.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/7000000/6850000/6846800/6846794/d5b38af4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Cabin](https://images.trvl-media.com/lodging/7000000/6850000/6846800/6846794/465fb1f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Land view from property](https://images.trvl-media.com/lodging/7000000/6850000/6846800/6846794/de3d8a22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/7000000/6850000/6846800/6846794/10fbb55c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Justin Trails Resort, LLC. [](https://www.expedia.ca/La-Crosse-Hotels-Justin-Trails-Resort.h6846794.Hotel-Information) Sparta 9.6/10 Exceptional (38) "To stay in peace, with nature and family, and with your Dog, I do recommend, the breakfast was delicious, the space clean, it’s really a cozy cabin, and the owner super friendly!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Luciana CA $322 CA $342 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/La-Crosse-Hotels-Justin-Trails-Resort.h6846794.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/79000000/78400000/78396800/78396746/735ce085.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78400000/78396800/78396746/6ececfdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/79000000/78400000/78396800/78396746/20761426.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78400000/78396800/78396746/57318f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ready to become a real love bird? Beautiful cabin to wake up hearing song birds [](https://www.expedia.ca/Norwalk-Hotels-Entire-Vacation-Home-Hosted-By-Kirsty.h78396746.Hotel-Information) Norwalk 10/10 Exceptional (3) "Easy check in. Beautiful cabin. We will be back for sure!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dana S. S. CA $395 CA $466 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/Norwalk-Hotels-Entire-Vacation-Home-Hosted-By-Kirsty.h78396746.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/43000000/42290000/42282000/42281948/7885f03a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/43000000/42290000/42282000/42281948/90-ca47ed80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, music library](https://images.trvl-media.com/lodging/43000000/42290000/42282000/42281948/b06cd7b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, music library](https://images.trvl-media.com/lodging/43000000/42290000/42282000/42281948/63368f92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded Rustic Cabin [](https://www.expedia.ca/Cashton-Hotels-Secluded-Rustic-Cabin.h42281948.Hotel-Information) Cashton 9.8/10 Exceptional (54) "So relaxing and an amazing house" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ann W. CA $401 CA $674 total includes taxes & fees Jan 3 - Jan 4 [](https://www.expedia.ca/Cashton-Hotels-Secluded-Rustic-Cabin.h42281948.Hotel-Information) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/79000000/78400000/78397300/78397282/f7e078f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78400000/78397300/78397282/fbf95db8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78400000/78397300/78397282/dc169953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78400000/78397300/78397282/b94d41b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The best place for star gazing all night. [](https://www.expedia.ca/Norwalk-Hotels-Entire-Vacation-Home-Hosted-By-Kirsty.h78397282.Hotel-Information) Norwalk 10/10 Exceptional (9) "Just a quick get away for the weekend. Close access to local restaurants, breweries, beautiful landscape." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heidi C. CA $394 CA $475 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Norwalk-Hotels-Entire-Vacation-Home-Hosted-By-Kirsty.h78397282.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/79000000/78400000/78397300/78397300/d17d55f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78400000/78397300/78397300/9927b826.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78400000/78397300/78397300/bf35ae6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, foosball](https://images.trvl-media.com/lodging/79000000/78400000/78397300/78397300/7c917527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax and watch all the different wildlife pass by as you put life on pause [](https://www.expedia.ca/Norwalk-Hotels-The-Hideaway-Couples-Cabin.h78397300.Hotel-Information) Norwalk 9.0/10 Wonderful (2) "We had the pleasure of getting a little snow during our stay which was awesome.But the roads from the cabin were sloppy with the melt the following day and we had trouble getting out to go for a grocery run. Kirsty and Kyle were very helpful and were kind enough to bring us some coffee and flour. Really great folks and a very beautiful and private location. Great space to reset from reality. Highly recommend." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nick W. CA $426 CA $503 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/Norwalk-Hotels-The-Hideaway-Couples-Cabin.h78397300.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=2026-01-15&endDate=2026-01-16®ionId=6338411&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Portland Hotel Reviews ![Old Towne Motel](https://images.trvl-media.com/lodging/9000000/8270000/8269600/8269592/684f3044_y.jpg) ### Old Towne Motel 10/10 Excellent "The room was clean, the bed comfortable. The lady at the front desk was friendly and helpful. The location is good: easy in and out from the highway, yet quiet, in a rural setting. We had an accessible room, and the shower had a built-in seat, which I appreciated. We've stayed there before, and always found it to be a great place to stay." [](https://expedia.ca/La-Crosse-Hotels-Old-Towne-Motel.h8269592.Hotel-Information) ## Frequently asked questions ### How much does a winery hotel in Portland cost? ### Which area of Portland is best to stay in for vineyards and wineries? > For couples on a romantic escape, the tranquil surroundings of the vineyard area provide a great backdrop for memorable moments. Picture yourselves strolling hand-in-hand through sun-kissed vineyards, enjoying a leisurely picnic with a bottle of locally produced wine, or dining at a winery restaurant that features farm-to-table cuisine. The intimate atmosphere is ideal for rekindling connections while soaking in the beauty of the landscape. > > > Families will also find this area enchanting, as many wineries offer kid-friendly activities. For example, some venues host seasonal events, such as grape stomping or harvest festivals, ensuring fun for all ages. The blend of nature, learning opportunities, and outdoor activities makes it a wonderful destination for family bonding. ### What winery activities should we do in Portland? > For couples seeking a romantic day out, a vineyard tour at the nearby Wollersheim Winery is a great choice. Here, you can explore the picturesque grounds, learn about the winemaking process, and enjoy a tasting of their award-winning wines, including the renowned Prairie Fumé. The winery's beautiful gardens provide a lovely backdrop for a leisurely stroll, making it an ideal setting for creating cherished memories together. > > > Families will find that visiting the nearby Vines and Rushes Winery offers a fun and educational experience. The winery frequently hosts family-friendly events, including grape-stomping festivals and interactive vineyard tours. With spacious outdoor areas, children can play while parents sample delicious wines crafted from locally sourced grapes. > > > For those looking to take home a piece of the experience, many wineries, such as the charming Cedar Grove Winery, offer workshops on winemaking and blending sessions. These hands-on activities provide a unique insight into the craft and allow you to create your own custom bottle to enjoy later. ### How can I save on a winery hotel in Portland with Expedia? ### Is it cheaper to book flights and a winery hotel in Portland as a package deal? ### Can I cancel my winery hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [3 Star Hotels in West Salem ](https://www.expedia.ca/3Star-West-Salem-Hotels.s30-0-d602448.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Ontario ](https://www.expedia.ca/5Star-Ontario-Hotels.s50-0-d3000461926.Travel-Guide-Filter-Hotels) - [Avalanche Hotels ](https://www.expedia.ca/Avalanche-Hotels.d553248635975873682.Travel-Guide-Hotels) - [Rv Parks in Avalanche ](https://www.expedia.ca/Avalanche-RV-Parks.d553248635975873682-aaRVParks.Travel-Guide-Accommodation) - [Farmstay in Bangor ](https://www.expedia.ca/Bangor-Agritourism.d553248634983545858-aaAgritourism.Travel-Guide-Accommodation) - 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