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 $88 ![](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 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6290&startDate=2025-10-25&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=6290&startDate=2025-10-26&endDate=2025-10-27&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6290&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6290&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Ashland Hotels with a Pool ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/2600/2550/52d07efc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2600/2550/e0d19362.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/1000000/10000/2600/2550/69e23b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Windsor Inn Ashland 9.0/10 Wonderful (1001) "Location very convenient, close to I5 and close enough to downtown" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jenni CA $137 CA $153 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Medford-Hotels-Best-Western-Windsor-Inn.h2550.Hotel-Information) ![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) ![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) ![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) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/50000/42900/42817/e097575f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Flagship Inn of Ashland Ashland 8.8/10 Excellent (1103) "Great choice, nice hotel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine CA $79 CA $88 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Medford-Hotels-Flagship-Inn-Of-Ashland.h42817.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/916000/915968/3c8278b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/916000/915968/cf48b0cd.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) ### Timbers INN and Suites Ashland 8.6/10 Excellent (1013) "Solid place to stay for the price. Great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zackery CA $88 CA $98 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Medford-Hotels-Timbers-Motel.h915968.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) ![Garden](https://images.trvl-media.com/lodging/1000000/900000/893600/893586/be871e55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/900000/893600/893586/9552f303.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lithia Springs Resort Ashland 9.4/10 Exceptional (1009) "Lovely place, great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kirk CA $144 CA $174 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Medford-Hotels-Lithia-Springs-Resort.h893586.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/9300/9249/7fe2e00a.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) ### The Bard's Inn, BW Signature Collection by Best Western Historic Downtown District 8.6/10 Excellent (1006) "My favorite place to stay in Ashland. Clean and nice rooms, affordable, PERFECT location and great staff! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lindsey CA $139 CA $155 total includes taxes & fees Nov 15 - Nov 16 [](https://www.expedia.ca/Medford-Hotels-The-Bards-Inn.h9249.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) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/1000000/850000/845500/845432/fd8dc2cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Ashland by IHG Ashland 9.2/10 Wonderful (1011) "Nice clean hotel well located for travel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zachary CA $155 CA $173 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Medford-Hotels-Holiday-Inn-Express-Suites-Ashland.h845432.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) ![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) ![Courtyard](https://images.trvl-media.com/lodging/1000000/30000/28200/28139/w3456h2065x0y1-0cc9f674.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) ### Ashland Hills Hotel & Suites Ashland 9.0/10 Wonderful (1487) "Nice place to break up the drive from Seattle to San Francisco " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward CA $157 CA $189 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Medford-Hotels-Ashland-Hills-Hotel-Suites.h28139.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/3500/3448/9eb7c716.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) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/3500/3448/2ee8917d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Ashland Ashland 8.6/10 Excellent (1003) "Was a great stay at an excellent hotel, clean, friendly. Pool and Jacuzzi were great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandy CA $133 CA $135 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Medford-Hotels-Comfort-Inn-Suites.h3448.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/2acbb0d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/7b9348b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stratford Inn Siskiyou-Hargadine Historic District 9.4/10 Exceptional (1568) "Very nice place. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lauren CA $151 CA $169 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Medford-Hotels-Stratford-Inn.h2758881.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) ![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) ![Sunrise Suite](https://images.trvl-media.com/lodging/90000000/89660000/89657800/89657723/887e2bda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Creekside Suite | Living area](https://images.trvl-media.com/lodging/90000000/89660000/89657800/89657723/235e6367.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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carol CA $231 CA $234 total includes taxes & fees Oct 26 - Oct 27 [](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=2025-11-08&endDate=2025-11-09®ionId=6290&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Ashland Hotel Reviews ![Flagship Inn of Ashland](//images.trvl-media.com/lodging/1000000/50000/42900/42817/f8004dc1_y.jpg) ### Flagship Inn of Ashland 10/10 Excellent "Loved the waffles, so happy you provided bananas. It was so quiet and convenient and close to my friend’s hospital. Loved the Mexican restaurant so close to the hotel, and no problems parking. 👍" [](https://expedia.ca/Medford-Hotels-Flagship-Inn-Of-Ashland.h42817.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 "Good place to stay nice rooms just need remodeled" [](https://expedia.ca/Medford-Hotels-Comfort-Inn-Suites.h3448.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 "We really appreciated the free EV charger. It was a faster slow charger. " [](https://expedia.ca/Medford-Hotels-Best-Western-Windsor-Inn.h2550.Hotel-Information) ![Holiday Inn Express & Suites Ashland by IHG](//images.trvl-media.com/lodging/1000000/850000/845500/845432/2a6193b5_y.jpg) ### Holiday Inn Express & Suites Ashland by IHG 10/10 Excellent "Great stay! The hotel was very clean and pretty quiet considering there were quite a few guests there. Rooms were nice and big, great amenities and convenient location." [](https://expedia.ca/Medford-Hotels-Holiday-Inn-Express-Suites-Ashland.h845432.Hotel-Information) ![Timbers INN and Suites](//images.trvl-media.com/lodging/1000000/920000/916000/915968/7580c086_y.jpg) ### Timbers INN and Suites 10/10 Excellent "Very pet friendly. Room had dog bed and food dishes in it. Large room with coffee pot, microwave and small refrigerator. Very nice." [](https://expedia.ca/Medford-Hotels-Timbers-Motel.h915968.Hotel-Information) ![Stratford Inn](//images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/b7c87028_y.jpg) ### Stratford Inn 10/10 Excellent "Very nice place. " [](https://expedia.ca/Medford-Hotels-Stratford-Inn.h2758881.Hotel-Information) ![Lithia Springs Resort](//images.trvl-media.com/lodging/1000000/900000/893600/893586/a941912b_y.jpg) ### Lithia Springs Resort 10/10 Excellent "Did not have time for breakfast, sorry they are no longer serving the delicious homemade scones in the afternoon." [](https://expedia.ca/Medford-Hotels-Lithia-Springs-Resort.h893586.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 "Great location and nice room" [](https://expedia.ca/Medford-Hotels-The-Bards-Inn.h9249.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 "Clean room and helpful staff. Carpet in our room need to be changed hopefully to tile as it’s more hygienic." [](https://expedia.ca/Medford-Hotels-Ashland-Hills-Hotel-Suites.h28139.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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[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)