Title: Book the Best Hotels with POOL in Ashland in 2025 | Expedia.ca [Ashland Travel Guide](https://expedia.ca/Ashland.dx6290)[Hotels in Ashland](https://expedia.ca/Ashland-Hotels.d6290.Travel-Guide-Hotels)[Vacation Rentals in Ashland](https://expedia.ca/Ashland-Vacation-Rentals.d6290.Travel-Guide-VacationRentals)[Flights to Ashland](https://expedia.ca/Cheap-Flights-To-Ashland.d6290.Travel-Guide-Flights)[Things to do in Ashland](https://expedia.ca/Things-To-Do-In-Ashland.d6290.Travel-Guide-Activities)[Ashland Car Rentals](https://expedia.ca/Car-Rentals-In-Ashland.d6290.Car-Rental-Guide)[Ashland Vacation Packages](https://expedia.ca/Ashland.d6290.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/2827c471dbf315bcf8c417169ecc676c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Ashland, OR from CA $94 ![](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 Ashland Hotels with a Pool Tonight [Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6290&startDate=2025-10-11&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=6290&startDate=2025-10-12&endDate=2025-10-13&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6290&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6290&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Ashland Hotels with a Pool ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/50000/42900/42817/feabb486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/50000/42900/42817/1d583c5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, 2 Queen Beds (No Pets)](https://images.trvl-media.com/lodging/1000000/50000/42900/42817/37bd6cfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/50000/42900/42817/1f352a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Flagship Inn of Ashland Ashland 8.8/10 Excellent (1082) "Clean, quiet, nice pool area" CA $84 CA $94 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Medford-Hotels-Flagship-Inn-Of-Ashland.h42817.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/2600/2550/52d07efc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/2600/2550/69e23b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/2600/2550/6d4857ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/2600/2550/ae66d7ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Windsor Inn Ashland 9.0/10 Wonderful (1006) "The room was clean and property very nice" CA $137 CA $153 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Medford-Hotels-Best-Western-Windsor-Inn.h2550.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/920000/916000/915968/7580c086.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Room, 3 Queen Beds (No Pets Allowed)](https://images.trvl-media.com/lodging/1000000/920000/916000/915968/e32a2cac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/916000/915968/3c8278b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 Queen Beds With Kitchen (No Pets Allowed) | Private kitchen](https://images.trvl-media.com/lodging/1000000/920000/916000/915968/10a08da4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Timbers INN and Suites Ashland 8.6/10 Excellent (1004) "Staff were incredibly welcoming, and the room was very nice." CA $88 CA $98 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Medford-Hotels-Timbers-Motel.h915968.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/5f7e6be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/b7c87028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/2acbb0d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Two Queen Room, Mountainside | Mountain view](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/4093c3d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stratford Inn Siskiyou-Hargadine Historic District 9.4/10 Exceptional (1566) "The hotel is exceptionally clean and very friendly!" CA $122 CA $137 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Medford-Hotels-Stratford-Inn.h2758881.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/850000/845500/845432/87bbee17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/850000/845500/845432/3bf5b42a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/850000/845500/845432/5b2299a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/850000/845500/845432/e1af2c81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Ashland by IHG Ashland 9.2/10 Wonderful (1001) "Nice clean hotel well located for travel" CA $147 CA $164 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Medford-Hotels-Holiday-Inn-Express-Suites-Ashland.h845432.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/3500/3448/cedb1fe4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/3500/3448/1be41ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/3500/3448/9eb7c716.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/10000/3500/3448/ac72a052.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Ashland Ashland 8.6/10 Excellent (1011) "Staff at check in was great." CA $135 CA $137 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Medford-Hotels-Comfort-Inn-Suites.h3448.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/28200/28139/1fd43c31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/28200/28139/3cd7d8f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/30000/28200/28139/w3456h2065x0y1-0cc9f674.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/30000/28200/28139/97525808.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ashland Hills Hotel & Suites Ashland 9.0/10 Wonderful (1479) "Very friendly staff." CA $157 CA $189 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Medford-Hotels-Ashland-Hills-Hotel-Suites.h28139.Hotel-Information) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/9300/9249/4ed86249.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9300/9249/d3116ae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/9300/9249/eed498c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9300/9249/80dea5e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bard's Inn, BW Signature Collection by Best Western Historic Downtown District 8.6/10 Excellent (1002) "My favorite place to stay in Ashland. Clean and nice rooms, affordable, PERFECT location and great staff! " CA $153 CA $170 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Medford-Hotels-The-Bards-Inn.h9249.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/900000/893600/893586/f07c8552.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Winery](https://images.trvl-media.com/lodging/1000000/900000/893600/893586/49a665aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Garden) | Private kitchenette](https://images.trvl-media.com/lodging/1000000/900000/893600/893586/ccf3a4bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/900000/893600/893586/be871e55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lithia Springs Resort Ashland 9.4/10 Exceptional (1002) "Lovely place, great staff" CA $183 CA $207 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Medford-Hotels-Lithia-Springs-Resort.h893586.Hotel-Information) ![Free daily full breakfast](https://images.trvl-media.com/lodging/90000000/89660000/89657800/89657723/7ef065ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sunrise Suite](https://images.trvl-media.com/lodging/90000000/89660000/89657800/89657723/887e2bda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/90000000/89660000/89657800/89657723/59c0fafd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89660000/89657800/89657723/306c76f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Willows Inn and Estate Ashland 9.8/10 Exceptional (32) "Beautiful setting close to downtown. Pool is marvelous!" CA $271 CA $275 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Ashland-Hotels-Country-Willows-Inn-And-Estate.h89657723.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=2025-10-25&endDate=2025-10-26®ionId=6290&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Ashland Hotel Reviews ![Timbers INN and Suites](//images.trvl-media.com/lodging/1000000/920000/916000/915968/7580c086_y.jpg) ### Timbers INN and Suites 10/10 Excellent "Nicely updated property." [](https://expedia.ca/Medford-Hotels-Timbers-Motel.h915968.Hotel-Information) ![Comfort Inn & Suites Ashland](//images.trvl-media.com/lodging/1000000/10000/3500/3448/9eb7c716_y.jpg) ### Comfort Inn & Suites Ashland 10/10 Excellent "PERFECT!!" [](https://expedia.ca/Medford-Hotels-Comfort-Inn-Suites.h3448.Hotel-Information) ![The Bard's Inn, BW Signature Collection by Best Western](//images.trvl-media.com/lodging/1000000/10000/9300/9249/80dea5e6_y.jpg) ### The Bard's Inn, BW Signature Collection by Best Western 10/10 Excellent "Clean room. Great location. Friendly staff" [](https://expedia.ca/Medford-Hotels-The-Bards-Inn.h9249.Hotel-Information) ![Lithia Springs Resort](//images.trvl-media.com/lodging/1000000/900000/893600/893586/a941912b_y.jpg) ### Lithia Springs Resort 10/10 Excellent "We enjoyed a quiet stay in one of the suites. The staff were friendly and helpful. The beds were very comfortable and everything was clean. We had fun walking around the grounds and seeing a group of wild turkeys wander past. " [](https://expedia.ca/Medford-Hotels-Lithia-Springs-Resort.h893586.Hotel-Information) ![Flagship Inn of Ashland](//images.trvl-media.com/lodging/1000000/50000/42900/42817/f8004dc1_y.jpg) ### Flagship Inn of Ashland 10/10 Excellent "Clean, quiet, nice pool area" [](https://expedia.ca/Medford-Hotels-Flagship-Inn-Of-Ashland.h42817.Hotel-Information) ![Stratford Inn](//images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/b7c87028_y.jpg) ### Stratford Inn 10/10 Excellent "Lovely and friendly staff, clean and confortable, convenient to downtown!" [](https://expedia.ca/Medford-Hotels-Stratford-Inn.h2758881.Hotel-Information) ![Ashland Hills Hotel & Suites](//images.trvl-media.com/lodging/1000000/30000/28200/28139/3cd7d8f2_y.jpg) ### Ashland Hills Hotel & Suites 10/10 Excellent "Very friendly staff." [](https://expedia.ca/Medford-Hotels-Ashland-Hills-Hotel-Suites.h28139.Hotel-Information) ![Best Western Windsor Inn](//images.trvl-media.com/lodging/1000000/10000/2600/2550/e0d19362_y.jpg) ### Best Western Windsor Inn 10/10 Excellent "The room was clean and property very nice" [](https://expedia.ca/Medford-Hotels-Best-Western-Windsor-Inn.h2550.Hotel-Information) ![Cedarwood Inn of Ashland](//images.trvl-media.com/lodging/3000000/2050000/2042000/2041971/37ac672b_y.jpg) ### Cedarwood Inn of Ashland 10/10 Excellent "Friendly staff and reasonable prices. Room smelled of smoke and was missing window screen so the flies came in. " [](https://expedia.ca/Medford-Hotels-Cedarwood-Inn-Of-Ashland.h2041971.Hotel-Information) ## Frequently asked questions ### What's it like visiting Ashland? > If lounging by a pool is your idea of the perfect getaway, you might want to think about welcoming Ashland, which offers 6 places to stay with pools. While you're visiting, you can explore attractions like Allen Elizabethan Theatre and Oregon Shakespeare Festival, and then take it easy poolside at one of the accommodations in Ashland that guests like for their pools. ### What are some hotels with pools in Ashland? > [Stratford Inn](https://www.expedia.ca/Medford-Hotels-Stratford-Inn.h2758881.Hotel-Information): Features a children's pool, an indoor pool, and free self parking. [Flagship Inn of Ashland](https://www.expedia.ca/Medford-Hotels-Flagship-Inn-Of-Ashland.h42817.Hotel-Information): Offers daily, a seasonal outdoor pool, and free self parking. [Country Willows Inn and Estate](https://www.expedia.ca/Ashland-Hotels-Country-Willows-Inn-And-Estate.h89657723.Hotel-Information): Provides spa services, a seasonal outdoor pool, and full. [Arden Forest Inn](https://www.expedia.ca/Medford-Hotels-Arden-Forest-Inn.h46085022.Hotel-Information): Features a snack bar/deli, a seasonal outdoor pool, and free self parking. [Super 8 by Wyndham Ashland](https://www.expedia.ca/Ashland-Hotels-Super-8-By-Wyndham-Ashland.h459940.Hotel-Information): Offers free self parking, a pool, and complimentary wireless internet access. ### How many pool hotels are there in Ashland? > Expedia has 6 hotels in Ashland for your poolside break. ### What is there to see and do in Ashland? > Make a point to visit attractions like Lithia Park and ScienceWorks Hands-On Museum. Discover sights such as Allen Elizabethan Theatre, Oregon Shakespeare Festival, and Oregon Cabaret Theatre during your stay. Ashland appeals to visitors with its picturesque gardens, popular theater scene, and array of dining options. ### When is the best time to book a hotel with a pool in Ashland? > Taking into account the local weather in Ashland is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and July with an average temp of 65°F, while the coldest months are December and January with an average of 37°F. 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[Motels in Phoenix](https://www.expedia.ca/Phoenix-Motels.d6047195-aaMotels.Travel-Guide-Accommodation) - [Resorts in Phoenix](https://www.expedia.ca/Phoenix-Resort-Hotels.d6047195-aaResortHotels.Travel-Guide-Accommodation) - [Townhomes in Phoenix](https://www.expedia.ca/Phoenix-Townhomes.d6047195-aaTownhomes.Travel-Guide-Accommodation) - [Hotels near Rogue Valley Country Club](https://www.expedia.ca/Rogue-Valley-Country-Club-Hotels.0-l6078463-0.Travel-Guide-Filter-Hotels) - [Best Western Hotels in Skidmore Academy Historic District](https://www.expedia.ca/Skidmore-Academy-Historic-District-Ashland-Hotels-Best-Western.0-n553248635976482103-0--bBestWestern.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Skidmore Academy Historic District](https://www.expedia.ca/Skidmore-Academy-Historic-District-Ashland-Hotels-Pet-Friendly-Hotel.0-n553248635976482103-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Skidmore Academy Historic District Hotels](https://www.expedia.ca/Skidmore-Academy-Historic-District-Ashland-Hotels.0-n553248635976482103-0.Travel-Guide-Filter-Hotels) - 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[Flights from New York (JFK) to Ashland (AHM)](https://www.expedia.ca/lp/flights/jfk/ahm/new-york-to-ashland) - [Flights from Kuwait City (KWI) to Ashland (AHM)](https://www.expedia.ca/lp/flights/kwi/ahm/kuwait-city-to-ashland) - [Flights from Medford (MFR) to Ashland (AHM)](https://www.expedia.ca/lp/flights/mfr/ahm/medford-to-ashland) - [Flights from Minneapolis (MSP) to Ashland (AHM)](https://www.expedia.ca/lp/flights/msp/ahm/minneapolis-to-ashland) - [Flights from Oakland (OAK) to Ashland (AHM)](https://www.expedia.ca/lp/flights/oak/ahm/oakland-to-ashland) - [Flights from Ontario (ONT) to Ashland (AHM)](https://www.expedia.ca/lp/flights/ont/ahm/ontario-to-ashland) - [Flights from Portland (PDX) to Ashland (AHM)](https://www.expedia.ca/lp/flights/pdx/ahm/portland-to-ashland) - [Flights from San Diego (SAN) to Ashland (AHM)](https://www.expedia.ca/lp/flights/san/ahm/san-diego-to-ashland) - [Flights from San Antonio (SAT) to Ashland (AHM)](https://www.expedia.ca/lp/flights/sat/ahm/san-antonio-to-ashland) - 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[Visit Skidmore Academy Historic District](https://www.expedia.ca/Ashland-Skidmore-Academy-Historic-District.dx553248635976482103) - [Edenvale Winery](https://www.expedia.ca/EdenVale-Winery-Medford.d6087459.Vacation-Attraction) - [Visit Medford](https://www.expedia.ca/Medford.dx602702) - [Thomas Theatre](https://www.expedia.ca/Thomas-Theatre-Historic-Downtown-District.d6078459.Vacation-Attraction) - [Car rental Talent](https://www.expedia.ca/Car-Rentals-In-Talent.d6347896.Car-Rental-Guide) - [Book Hotels with a Pool in Ashland on Expedia.com](https://www.expedia.com/Ashland-Hotels-Hotel-With-Pool.0-0-d6290-tHotelwithPool.Travel-Guide-Filter-Hotels)