Title: Book the Best Lake Oswego WINERY Hotels in 2025 | Expedia.ca [Lake Oswego Travel Guide](https://expedia.ca/Lake-Oswego.dx8512)[Hotels in Lake Oswego](https://expedia.ca/Lake-Oswego-Hotels.d8512.Travel-Guide-Hotels)[Vacation Rentals in Lake Oswego](https://expedia.ca/Lake-Oswego-Vacation-Rentals.d8512.Travel-Guide-VacationRentals)[Flights to Lake Oswego](https://expedia.ca/Cheap-Flights-To-Lake-Oswego.d8512.Travel-Guide-Flights)[Things to do in Lake Oswego](https://expedia.ca/Things-To-Do-In-Lake-Oswego.d8512.Travel-Guide-Activities)[Lake Oswego Car Rentals](https://expedia.ca/Car-Rentals-In-Lake-Oswego.d8512.Car-Rental-Guide)[Lake Oswego Vacation Packages](https://expedia.ca/Lake-Oswego.d8512.Destination-Travel-Guides) ![A tangle of trees and understory vegetation thrive in Tryon State Park, Lake Oswego, Oregon. This part of the country is home to temperate rainforests which serve as habitats for many species.](https://images.trvl-media.com/place/8512/4fbde8ea-639e-4dcf-8a7d-5e640cded489.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Lake Oswego, OR from CA $102 - ![](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 Lake Oswego Winery Hotels Tonight [Nov 18 - Nov 19](https://www.expedia.ca/Hotel-Search?regionId=8512&startDate=2025-11-18&endDate=2025-11-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 19 - Nov 20](https://www.expedia.ca/Hotel-Search?regionId=8512&startDate=2025-11-19&endDate=2025-11-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=8512&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=8512&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Lake Oswego Winery Hotels ![Sundeck](https://images.trvl-media.com/lodging/2000000/1140000/1135600/1135564/782d62ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1140000/1135600/1135564/965d10bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1140000/1135600/1135564/a5ba7115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 Queen Bed, Lake View](https://images.trvl-media.com/lodging/2000000/1140000/1135600/1135564/3677081b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakeshore Inn Lakewood 8.4/10 Very good (385) "Beautiful sunny spot right on the lake and walking distance to all the restaurants and shops. So fun to watch the boats and sit on the deck. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Miles CA $196 CA $222 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Portland-Hotels-Lakeshore-Inn.h1135564.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/38000000/37970000/37965900/37965836/5a89240a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/38000000/37970000/37965900/37965836/9e8413b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/38000000/37970000/37965900/37965836/3095bee2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, hypo-allergenic bedding, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/38000000/37970000/37965900/37965836/3596d94b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Casa with Luxury Amenities -hot tub and massage chair Oak Creek 9.8/10 Exceptional (113) "Very nice home. Very responsive property manager. Flexible for pets and excellent backyard for dogs to enjoy. Would definitely stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeff M. CA $316 CA $488 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Portland-Hotels-La-Casa-With-Luxury-Amenities-Hot-Tub-And-Massage-Chair.h37965836.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88080000/88076100/88076075/7423a249.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/89000000/88080000/88076100/88076075/881624be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, travel crib, free WiFi](https://images.trvl-media.com/lodging/89000000/88080000/88076100/88076075/628b3574.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/89000000/88080000/88076100/88076075/b76d8d6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upscale and quiet new home in Lake Oswego with amazing Patio Lake Oswego 10/10 Exceptional (43) "Gorgeous new home in an upscale, safe neighborhood. My 2 daughters and I had a lovely stay here and would definitely recommend this place for small groups who enjoy a high end rental. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristin C. CA $278 CA $635 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Portland-Hotels-Upscale-And-Quiet-New-Home-In-Lake-Oswego-With-Amazing-Patio.h88076075.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/340000/330600/330558/b2e58e4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/340000/330600/330558/144d97a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/340000/330600/330558/a51783ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/1000000/340000/330600/330558/a98b8c48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Paramount Hotel Downtown Portland 9.2/10 Wonderful (2996) "Beautiful hotel, staff is amazing, great downtown location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shelley CA $128 CA $150 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Portland-Hotels-The-Paramount-Hotel.h330558.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/13000000/12290000/12280700/12280688/93730b77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/13000000/12290000/12280700/12280688/d97449fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12290000/12280700/12280688/2629a6da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/13000000/12290000/12280700/12280688/cdd82fdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### McMenamins Edgefield Troutdale 9.0/10 Wonderful (364) "I loved wine tasting in the winery,the pool hall bar was nice but the best part was the soaking pool." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sherry CA $156 CA $177 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Portland-Hotels-McMenamins-Edgefield.h12280688.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/36000000/35210000/35205700/35205632/c236d611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served](https://images.trvl-media.com/lodging/36000000/35210000/35205700/35205632/ca060547.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/36000000/35210000/35205700/35205632/ee10dafe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/36000000/35210000/35205700/35205632/ee9e2e69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### KEX Portland Northeast Portland 9.0/10 Wonderful (524) "We had a fabulous stay, very comfortable and clean! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kara CA $115 CA $151 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Portland-Hotels-KEX-Portland.h35205632.Hotel-Information) ![Luxury Suite, 1 Bedroom (Hospitality Suite) | In-room dining](https://images.trvl-media.com/lodging/1000000/20000/20000/19921/e8cf5bcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/20000/19921/b8471ae7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/20000/20000/19921/6b0c4581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-fridge, microwave](https://images.trvl-media.com/lodging/1000000/20000/20000/19921/d6c913ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mark Spencer Hotel Downtown Portland 9.2/10 Wonderful (1846) "Great hotel in a great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $88 CA $102 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Portland-Hotels-Mark-Spencer-Hotel.h19921.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/62000000/61350000/61340900/61340845/de097a73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/62000000/61350000/61340900/61340845/5e51dd8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/62000000/61350000/61340900/61340845/1bf83682.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/62000000/61350000/61340900/61340845/34cdd815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Moxy Portland Downtown Downtown Portland 9.0/10 Wonderful (1341) "The staff were all friendly and helpful. We really liked the cool vibes of the hotel. The bar is really fun!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jenny CA $139 CA $161 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Portland-Hotels-Moxy-Portland-Downtown.h61340845.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/77000000/76910000/76905100/76905063/3d49c196.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Queen Room with Shared Bathroom (Self Check-in)](https://images.trvl-media.com/lodging/77000000/76910000/76905100/76905063/c0b97f45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Triple Room with Shared Bathroom (Self Check-in)](https://images.trvl-media.com/lodging/77000000/76910000/76905100/76905063/b86008d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Queen Room (Self Check-in)](https://images.trvl-media.com/lodging/77000000/76910000/76905100/76905063/1b67f601.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Clyde Hotel Portland by Kasa Living Downtown Portland 8.6/10 Excellent (554) "Great staff, outstanding location, great quiet rooms, great value. Couldn't ask for more. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darrell CA $97 CA $158 total includes taxes & fees Dec 5 - Dec 6 [](https://www.expedia.ca/Portland-Hotels-The-Clyde-Hotel-Portland-By-Kasa.h76905063.Hotel-Information) ![Meeting facility](https://images.trvl-media.com/lodging/18000000/17400000/17395500/17395433/e0472e48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served, American cuisine](https://images.trvl-media.com/lodging/18000000/17400000/17395500/17395433/1d90bc21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17400000/17395500/17395433/e5e381b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/18000000/17400000/17395500/17395433/f49b4b71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Duniway Portland A Hilton Hotel Downtown Portland 8.6/10 Excellent (1002) "Great location and facilities " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $160 CA $185 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Portland-Hotels-The-Duniway-Portland-A-Hilton-Hotel.h17395433.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=2025-12-02&endDate=2025-12-03®ionId=8512&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Lake Oswego Hotel Reviews ### Holiday Inn Airport - Portland by IHG 10/10 Excellent "Very good, but the parking are 24.99 per day" [](https://expedia.ca/Portland-Hotels-Holiday-Inn-Airport-Portland.h11678.Hotel-Information) ### Sentinel Hotel 10/10 Excellent "Great staff and nice room" [](https://expedia.ca/Portland-Hotels-Sentinel.h1854.Hotel-Information) ### Embassy Suites by Hilton Portland Downtown 10/10 Excellent "Clean room " [](https://expedia.ca/Portland-Hotels-Embassy-Suites-By-Hilton-Portland-Downtown.h74615.Hotel-Information) ### Mark Spencer Hotel 10/10 Excellent "Clean room, excellent service " [](https://expedia.ca/Portland-Hotels-Mark-Spencer-Hotel.h19921.Hotel-Information) ### Courtyard by Marriott Portland City Center 10/10 Excellent "Everything went well and the staffs are helpful " [](https://expedia.ca/Portland-Hotels-Courtyard-By-Marriott-Portland-City-Center.h2469036.Hotel-Information) ### The Paramount Hotel 10/10 Excellent "Good small hotel option in downtown Portland, perfectly safe for women travelers. " [](https://expedia.ca/Portland-Hotels-The-Paramount-Hotel.h330558.Hotel-Information) ### Red Lion Hotel Portland Airport 10/10 Excellent "Super stay " [](https://expedia.ca/Portland-Hotels-Red-Lion-Hotel-Portland-Airport.h24159.Hotel-Information) ### Country Inn & Suites by Radisson, Portland International Airport, OR 10/10 Excellent "Breakfast was good, fresh. Room was spacious and clean" [](https://expedia.ca/Portland-Hotels-Country-Inn-Suites-By-Radisson.h116495.Hotel-Information) ### Heathman Hotel 10/10 Excellent "Our stay did not come with free breakfast but the options there were fresh and tasty. Free coffee and tea if you walk into the main lobby. Cozy rooms with a bunch of amenities. Even had a selection of drinks and snacks in the room to buy if you didn't want to walk to Safeway. We used the valet for our stay since we didn't want to worry about trying to find parking. 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[West Portland Park Hotels](https://www.expedia.ca/West-Portland-Park-Portland-Hotels.0-n553248635976387500-0.Travel-Guide-Filter-Hotels) - [Flights to Gladstone](https://www.expedia.ca/Cheap-Flights-To-Gladstone.d55724.Travel-Guide-Flights) - [Flights to Portland](https://www.expedia.ca/Cheap-Flights-To-Portland.d178299.Travel-Guide-Flights) - [Bike Gallery](https://www.expedia.ca/Bike-Gallery-First-Addition.d553248621532650324.Vacation-Attraction) - [Visit Ardenwald](https://www.expedia.ca/Portland-Ardenwald.dx553248635976477500) - [Visit Multnomah Village](https://www.expedia.ca/Portland-Multnomah-Village.dx553248635976381748) - [Visit Walluga](https://www.expedia.ca/Portland-Walluga.dx553248635976479200) - [Car rental Milwaukie](https://www.expedia.ca/Car-Rentals-In-Milwaukie.d8645.Car-Rental-Guide) - [Book Winery Hotels in Lake Oswego on Expedia.com](https://www.expedia.com/Lake-Oswego-Hotels-Winery-Hotel.0-0-d8512-tWineryHotel.Travel-Guide-Filter-Hotels)