Title: Book the Best Portland WINERY Hotels in 2026 | Expedia.ca [Portland Travel Guide](https://expedia.ca/Portland.dx181420)[Hotels in Portland](https://expedia.ca/Portland-Hotels.d181420.Travel-Guide-Hotels)[Vacation Rentals in Portland](https://expedia.ca/Portland-Vacation-Rentals.d181420.Travel-Guide-VacationRentals)[Flights to Portland](https://expedia.ca/Cheap-Flights-To-Portland.d181420.Travel-Guide-Flights)[Things to do in Portland](https://expedia.ca/Things-To-Do-In-Portland.d181420.Travel-Guide-Activities)[Portland Car Rentals](https://expedia.ca/Car-Rentals-In-Portland.d181420.Car-Rental-Guide)[Portland Vacation Packages](https://expedia.ca/Portland.d181420.Destination-Travel-Guides) ![Portland Head Light which includes rocky coastline, general coastal views and a lighthouse](https://images.trvl-media.com/place/6077212/de0c2dd0-6073-4b78-9982-6545fcddd303.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6077212/de0c2dd0-6073-4b78-9982-6545fcddd303.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 Portland Winery Hotels Tonight [Feb 6 - Feb 7](https://www.expedia.ca/Hotel-Search?regionId=181420&startDate=2026-02-06&endDate=2026-02-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 7 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=181420&startDate=2026-02-07&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=181420&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=181420&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Portland hotels with winery ![View from room](https://images.trvl-media.com/lodging/8000000/7490000/7488200/7488159/06fb9956.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7490000/7488200/7488159/497a6028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/8000000/7490000/7488200/7488159/2e3cf56e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Bay View](https://images.trvl-media.com/lodging/8000000/7490000/7488200/7488159/bc24f75b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Portland Downtown - Old Port Square [](https://www.expedia.ca/Portland-Hotels-Hyatt-Place-Portland-Old-Port.h7488159.Hotel-Information) Downtown Portland 9.0/10 Wonderful (1,321 reviews) "Amazing location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cassandra CA $123 CA $136 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Portland-Hotels-Hyatt-Place-Portland-Old-Port.h7488159.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/3000000/2810000/2803900/2803802/5ba6b9c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2810000/2803900/2803802/12c972ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2810000/2803900/2803802/115a7439.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/3000000/2810000/2803900/2803802/a3d98684.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn Portland Downtown/Waterfront [](https://www.expedia.ca/Portland-Hotels-Residence-Inn-By-Marriott-Portland-Downtown-Waterfront.h2803802.Hotel-Information) East Bayside 8.8/10 Excellent (1,002 reviews) "Great parking, friendly staff, good healthy breakfast options, good location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ben CA $130 CA $144 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Portland-Hotels-Residence-Inn-By-Marriott-Portland-Downtown-Waterfront.h2803802.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/96000000/95700000/95697200/95697174/be8e38da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business Room](https://images.trvl-media.com/lodging/96000000/95700000/95697200/95697174/b7e27ec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, sauna, body treatments, deep-tissue massages](https://images.trvl-media.com/lodging/96000000/95700000/95697200/95697174/c46ba49b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room | Exterior](https://images.trvl-media.com/lodging/96000000/95700000/95697200/95697174/7fe25763.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Longfellow Hotel [](https://www.expedia.ca/Portland-Hotels-Longfellow-Hotel.h95697174.Hotel-Information) Parkside 9.6/10 Exceptional (143 reviews) "We loved our stay. Great staff, room was nice, cafe very good and the Town Car service for rides, so convenient!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rosanne [](https://www.expedia.ca/Portland-Hotels-Longfellow-Hotel.h95697174.Hotel-Information) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/9900/9842/50ab7409.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/10000/9900/9842/a89c1824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/10000/9900/9842/b67ac563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gazebo](https://images.trvl-media.com/lodging/1000000/10000/9900/9842/c68a2781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fireside Inn & Suites Portland [](https://www.expedia.ca/Portland-Hotels-Fireside-Inn-Suites.h9842.Hotel-Information) Nasons Corner 8.0/10 Very good (1,001 reviews) "Easy check in, cozy and clean 👍" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathryn CA $120 CA $133 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Portland-Hotels-Fireside-Inn-Suites.h9842.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/33000000/32440000/32432100/32432059/w1917h1645x3y0-1a82cf6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/33000000/32440000/32432100/32432059/fe48c018.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/33000000/32440000/32432100/32432059/w1920h1432x0y17-47ca72aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32440000/32432100/32432059/91a3f768.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Adorable Portland getaway on the Eastern Promenade [](https://www.expedia.ca/Portland-Hotels-Adorable-Portland-Getaway-On-The-Eastern-Promenade.h32432059.Hotel-Information) Munjoy Hill 9.6/10 Exceptional (128 reviews) "Tidy place in a great location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary M. CA $150 CA $279 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Portland-Hotels-Adorable-Portland-Getaway-On-The-Eastern-Promenade.h32432059.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/13000000/12750000/12743300/12743204/f3398d4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/13000000/12750000/12743300/12743204/w682h956x0y0-568677a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/13000000/12750000/12743300/12743204/926be017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12750000/12743300/12743204/8a9890d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blind Tiger Portland – Carleton Street [](https://www.expedia.ca/Portland-Hotels-Inn-On-Carleton.h12743204.Hotel-Information) West End 9.6/10 Exceptional (120 reviews) "Loved the place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen CA $258 CA $281 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Portland-Hotels-Inn-On-Carleton.h12743204.Hotel-Information) ![Premium bedding, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/10000/200/141/4cd3d996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/200/141/a368d804.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/200/141/6d18ad08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Efficiency Suite, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/200/141/e89f8f7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn & Suites South Portland [](https://www.expedia.ca/Portland-Hotels-Quality-Inn-Suites.h141.Hotel-Information) Sunset Park 6.6/10 (1,000 reviews) "Great rooms great service " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony CA $92 CA $100 total includes taxes & fees Mar 7 - Mar 8 [](https://www.expedia.ca/Portland-Hotels-Quality-Inn-Suites.h141.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/60000000/59960000/59959800/59959794/5c42ecc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, Netflix, streaming services](https://images.trvl-media.com/lodging/60000000/59960000/59959800/59959794/a3f31177.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59960000/59959800/59959794/72cf4bec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/60000000/59960000/59959800/59959794/824219c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious and Contemporary Condo in the Heart of Portland - Close to Beach [](https://www.expedia.ca/Portland-Hotels-Spacious-And-Contemporary-Condo-In-The-Heart-Of-Portland-Close-To-Beach.h59959794.Hotel-Information) East Bayside 8.8/10 Excellent (37 reviews) "Overall a pleasing stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mallory D. CA $182 CA $632 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Portland-Hotels-Spacious-And-Contemporary-Condo-In-The-Heart-Of-Portland-Close-To-Beach.h59959794.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71730000/71727700/71727615/ed9e532e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71730000/71727700/71727615/f3da9d64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/72000000/71730000/71727700/71727615/146b7a7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/72000000/71730000/71727700/71727615/6413d3e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Location, location! Prime- West End Studio. Walkable to entire city! [](https://www.expedia.ca/Portland-Hotels-Urban-Studio-In-An-Amazing.h71727615.Hotel-Information) West End 10/10 Exceptional (2 reviews) "It was perfect for what we were looking for, would absolutely stay there again. The stairs to the property are fire escape stairs, they are metal and steep. Overall great place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leslie P. CA $224 CA $416 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/Portland-Hotels-Urban-Studio-In-An-Amazing.h71727615.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/116000000/115810000/115807900/115807815/a51f5d91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115810000/115807900/115807815/89d6e8dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/116000000/115810000/115807900/115807815/ce200994.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115810000/115807900/115807815/f15474ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK [](https://www.expedia.ca/Westbrook-Hotels-Updated-Apartment-20-Mins-To-Portland.h115807815.Hotel-Information) Westbrook 10/10 Exceptional (6 reviews) "Nice historic place, restored to all modern standards and amenities, while retaining its historical charm. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aleksey I. CA $197 CA $574 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Westbrook-Hotels-Updated-Apartment-20-Mins-To-Portland.h115807815.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=2026-02-20&endDate=2026-02-21®ionId=181420&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Portland Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Hotels near Bayside Bowl ](https://www.expedia.ca/Bayside-Bowl-Hotels.0-l553248621532668077-0.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Cape Elizabeth ](https://www.expedia.ca/Cape-Elizabeth-Hotels-Beach-Hotel.0-0-d55620-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Cape Elizabeth ](https://www.expedia.ca/Cape-Elizabeth-Hotels-Boutique-Hotel.0-0-d55620-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Cape Elizabeth ](https://www.expedia.ca/Cape-Elizabeth-Hotels-Cheap-Hotels.0-0-d55620-tCheapHotels.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Cape Elizabeth ](https://www.expedia.ca/Cape-Elizabeth-Hotels-Honeymoon-Hotels.0-0-d55620-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - 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