Title: Book the Best Hotels with POOL in Winston in 2025 | Expedia.ca [Hotels in Winston](https://expedia.ca/Winston-Hotels.d6124402.Travel-Guide-Hotels)[Vacation Rentals in Winston](https://expedia.ca/Winston-Vacation-Rentals.d6124402.Travel-Guide-VacationRentals)[Flights to Winston](https://expedia.ca/Cheap-Flights-To-Winston.d6124402.Travel-Guide-Flights)[Things to do in Winston](https://expedia.ca/Things-To-Do-In-Winston.d6124402.Travel-Guide-Activities)[Winston Car Rentals](https://expedia.ca/Car-Rentals-In-Winston.d6124402.Car-Rental-Guide)[Winston Vacation Packages](https://expedia.ca/Winston.d6124402.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/43f0ab47d1f3578edeadf8a2b3b5b7cb.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Michelle Finseth # Find Hotels with a Pool in Winston, OR from CA $117 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Winston Hotels with a Pool Tonight [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=6124402&startDate=2025-10-02&endDate=2025-10-03&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=6124402&startDate=2025-10-03&endDate=2025-10-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6124402&startDate=2025-10-03&endDate=2025-10-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6124402&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winston Hotels with a Pool ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/16100/16066/f3af2ae0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/20000/16100/16066/91b3330a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16100/16066/81d2a043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/16100/16066/6950d5ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverfront Inn Roseburg Roseburg 8.6/10 Excellent (1401) "We enjoyed our stay!" CA $130 CA $143 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Roseburg-Hotels-Riverfront-Inn-Roseburg.h16066.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1790000/1784800/1784775/a796994f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1790000/1784800/1784775/8b128a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1784800/1784775/52200410.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Down comforters, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1790000/1784800/1784775/608fa78e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Hartford Lodge Sutherlin 9.0/10 Wonderful (1002) "Pretty nice hotel for a quick stop. Pool and jacuzzi is a nice touch." CA $150 CA $165 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Roseburg-Hotels-Best-Western-Plus-Hartford-Lodge.h1784775.Hotel-Information) ![Indoor pool, open 8:00 AM to 11:00 AM, sun loungers](https://images.trvl-media.com/lodging/23000000/22280000/22270800/22270751/1951ad21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/23000000/22280000/22270800/22270751/3b60422d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22280000/22270800/22270751/df80a59c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/23000000/22280000/22270800/22270751/3b1d8b77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Roseburg Roseburg 9.6/10 Exceptional (935) "Always love staying here " CA $212 CA $233 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Roseburg-Hotels-Hampton-Inn-Suites-Roseburg.h22270751.Hotel-Information) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/85000000/84100000/84099600/84099548/7b19a871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/85000000/84100000/84099600/84099548/75ce7237.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/85000000/84100000/84099600/84099548/371fa2b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/85000000/84100000/84099600/84099548/578dd407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Canyonville Canyonville 7.6/10 Good (434) "Great place to stay for an affordable price!" CA $115 CA $117 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Canyonville-Hotels-Canyonville-Inn.h84099548.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/22800/22705/83fd2fe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22800/22705/27e6bc41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/30000/22800/22705/81c558f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22800/22705/f1ad184a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Roseburg by IHG Roseburg 8.8/10 Excellent (1000) "Friendly staff, convenient location, river views" CA $199 CA $218 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Roseburg-Hotels-Holiday-Inn-Express-Roseburg.h22705.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/160000/159100/159048/0c6d6cb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/160000/159100/159048/e807ccc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/160000/159100/159048/e0f326ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/160000/159100/159048/ccce26bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Roseburg Roseburg 7.8/10 Good (1000) "Was a good stay!" CA $111 CA $122 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Roseburg-Hotels-Super-8-By-Wyndham-Roseburg.h159048.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17800/17750/f7817ddf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17800/17750/1a3bee3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/20000/17800/17750/c51ee531.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17800/17750/61f465bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Roseburg Roseburg 8.2/10 Very good (1003) "The staff was exceptional " CA $151 CA $165 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Roseburg-Hotels-Comfort-Inn.h17750.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/540000/539600/539504/d6502ad4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/540000/539600/539504/32f54617.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/540000/539600/539504/abf320fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/540000/539600/539504/41cd13e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites Roseburg North Near Medical Center Roseburg 8.0/10 Very good (1001) "Convenient location and easy parking." CA $142 CA $156 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Roseburg-Hotels-Sleep-Inn-Suites-Roseburg-North-Near-Medical-Center.h539504.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/7100/7049/847b12f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free breakfast](https://images.trvl-media.com/lodging/1000000/10000/7100/7049/c06638cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/7100/7049/66270df2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7100/7049/eff8e6cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Garden Villa Inn Roseburg 8.0/10 Very good (1000) "Great breakfast!" CA $172 CA $188 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Roseburg-Hotels-Best-Western-Garden-Villa-Inn.h7049.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/670000/663100/663067/603b7923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/670000/663100/663067/a981c12e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/670000/663100/663067/ff6da1e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/670000/663100/663067/f699f1d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Central Roseburg Roseburg 7.6/10 Good (693) "It was nice, it had what we needed for our one night stay" CA $117 CA $128 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Roseburg-Hotels-Quality-Inn-Central-Roseburg.h663067.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=2025-10-16&endDate=2025-10-17®ionId=6124402&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Winston Hotel Reviews ![Riverfront Inn Roseburg](//images.trvl-media.com/lodging/1000000/20000/16100/16066/81d2a043_y.jpg) ### Riverfront Inn Roseburg 10/10 Excellent "Friendly Staff " [](https://expedia.ca/Roseburg-Hotels-Riverfront-Inn-Roseburg.h16066.Hotel-Information) ![Super 8 by Wyndham Roseburg](//images.trvl-media.com/lodging/1000000/160000/159100/159048/ccce26bb_y.jpg) ### Super 8 by Wyndham Roseburg 10/10 Excellent "The front desk people are always so helpful. " [](https://expedia.ca/Roseburg-Hotels-Super-8-By-Wyndham-Roseburg.h159048.Hotel-Information) ![Best Western Plus Hartford Lodge](//images.trvl-media.com/lodging/2000000/1790000/1784800/1784775/608fa78e_y.jpg) ### Best Western Plus Hartford Lodge 10/10 Excellent "Room and pool were great, but the breakfast was phenomenal. " [](https://expedia.ca/Roseburg-Hotels-Best-Western-Plus-Hartford-Lodge.h1784775.Hotel-Information) ![Sleep Inn & Suites Roseburg North Near Medical Center](//images.trvl-media.com/lodging/1000000/540000/539600/539504/32f54617_y.jpg) ### Sleep Inn & Suites Roseburg North Near Medical Center 10/10 Excellent "Great experience! " [](https://expedia.ca/Roseburg-Hotels-Sleep-Inn-Suites-Roseburg-North-Near-Medical-Center.h539504.Hotel-Information) ![Best Western Garden Villa Inn](//images.trvl-media.com/lodging/1000000/10000/7100/7049/eff8e6cb_y.jpg) ### Best Western Garden Villa Inn 10/10 Excellent "Noisy a/c with confusing panel buttons. Spongy pillows were not very conforming and mattress was very firm, which was uncomfortable for us." [](https://expedia.ca/Roseburg-Hotels-Best-Western-Garden-Villa-Inn.h7049.Hotel-Information) ![Comfort Inn Roseburg](//images.trvl-media.com/lodging/1000000/20000/17800/17750/61f465bf_y.jpg) ### Comfort Inn Roseburg 10/10 Excellent "I’ll be honest and say I don’t typically stay at budget hotels, but I don’t feel like paying $150 more a night for the place across the street. I was happy with my stay and the comfort of the room. I had a good nights sleep. " [](https://expedia.ca/Roseburg-Hotels-Comfort-Inn.h17750.Hotel-Information) ![Holiday Inn Express Roseburg by IHG](//images.trvl-media.com/lodging/1000000/30000/22800/22705/a366b61d_y.jpg) ### Holiday Inn Express Roseburg by IHG 10/10 Excellent "Well appointed interior design and very comfortable bed " [](https://expedia.ca/Roseburg-Hotels-Holiday-Inn-Express-Roseburg.h22705.Hotel-Information) ![Quality Inn Central Roseburg](//images.trvl-media.com/lodging/1000000/670000/663100/663067/f699f1d4_y.jpg) ### Quality Inn Central Roseburg 10/10 Excellent "Clean and quiet " [](https://expedia.ca/Roseburg-Hotels-Quality-Inn-Central-Roseburg.h663067.Hotel-Information) ![Rosewood Inn and Suites](//images.trvl-media.com/lodging/1000000/920000/920000/919945/198b0811_y.jpg) ### Rosewood Inn and Suites 10/10 Excellent "The reptionist was excellent. She " [](https://expedia.ca/Roseburg-Hotels-Rosewood-Inn-And-Suites.h919945.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Winston? > [Safari Inn](https://www.expedia.ca/Roseburg-Hotels-Safari-Inn.h8777128.Hotel-Information): Features daily, an outdoor pool, and complimentary wired internet access. [The Watusi Place - A Modern Umpqua Valley Getaway](https://www.expedia.ca/Winston-Hotels-The-Watusi-Place-A-Modern-Umpqua-Valley-Getaway.h78301309.Hotel-Information): Offers daily, a pool, and free self parking. [Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen](https://www.expedia.ca/Winston-Hotels-Large-7-Bd-5-Bath-House-A-Few-Miles-From-Wildlife-Safari-Gourmet-Kitchen.h40001956.Hotel-Information): Features buffet, an indoor pool, and free self parking. [Family-friendly Winston Vacation Rental w/ Deck!](https://www.expedia.ca/Winston-Hotels-Family-Friendly-Winston-Vacation-Rental-W-Deck.h102048459.Hotel-Information): Features buffet, an indoor pool, and free self parking. [Riverfront Inn Roseburg](https://www.expedia.ca/Roseburg-Hotels-Riverfront-Inn-Roseburg.h16066.Hotel-Information): Offers complimentary wired internet access, a seasonal outdoor pool, and free self parking. ### What is there to see and do in Winston? > Make a point to visit attractions like South Umpqua River and Wildlife Safari. Discover sights such as Abacela Winery during your stay. Take in the natural beauty of Winston with the wildlife. ### When is the best time to book a hotel with a pool in Winston? > Taking into account the local weather in Winston can help you maximize your time at the pool during your trip. The hottest months are usually August and July with an average temp of 62°F, while the coldest months are December and February with an average of 40°F. 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