Title: Book the Best Hotels with BARS 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 Bar in Ashland, OR from CA $155 ![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 Ashland Hotels with Bar ## Top Ashland Hotels with Bar ![Panoramic Room, 1 King Bed, Jetted Tub, Mountain View | Terrace/patio](https://images.trvl-media.com/lodging/13000000/12380000/12372400/12372363/2d34db80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family House | Private kitchen](https://images.trvl-media.com/lodging/13000000/12380000/12372400/12372363/52c43a54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/13000000/12380000/12372400/12372363/609741f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds](https://images.trvl-media.com/lodging/13000000/12380000/12372400/12372363/01670d2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Callahan's Mountain Lodge Ashland 8.8/10 Excellent (1170) "Very intimate setting, amazing staff and wonderful restaurant and bar." CA $161 CA $185 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Medford-Hotels-Callahans-Mountain-Lodge.h12372363.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/39000000/38910000/38900300/38900286/6a1781f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Tasting room](https://images.trvl-media.com/lodging/39000000/38910000/38900300/38900286/d56112cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38910000/38900300/38900286/5af57880.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 1 King Bed, Japanese Maple Suite | Living area](https://images.trvl-media.com/lodging/39000000/38910000/38900300/38900286/de1e7991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hummingbird Estate Wine & Suites Central Point 9.6/10 Exceptional (138) "Beautiful facility - enjoyed the stay! " CA $217 CA $220 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Medford-Hotels-Hummingbird-Estate-Wine-Suites.h38900286.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/20000000/19570000/19562400/19562376/0103a1b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19570000/19562400/19562376/64da398a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/20000000/19570000/19562400/19562376/674fb21f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/20000000/19570000/19562400/19562376/51d82ede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Resort at Eagle Point Eagle Point 9.4/10 Exceptional (263) "Great place to stay! " CA $269 CA $287 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Medford-Hotels-Resort-At-Eagle-Point.h19562376.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/104000000/103030000/103027800/103027740/2ca84916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/104000000/103030000/103027800/103027740/707ecad9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103030000/103027800/103027740/15118f80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, River View](https://images.trvl-media.com/lodging/104000000/103030000/103027800/103027740/926a3f78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Lindsay Lodge & Restaurant Jacksonville 8.6/10 Excellent (30) "Just an awesome place with amazing food" CA $298 CA $303 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Jacksonville-Hotels-The-Lindsay-Lodge-Restaurant.h103027740.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/28200/28139/1fd43c31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/28200/28139/9f192341.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 (1463) "Great clean spacious rooms with a cool retro vibe" CA $152 CA $183 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Medford-Hotels-Ashland-Hills-Hotel-Suites.h28139.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/86190d91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/cd01e6a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/c5aa855a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed, City View | View from room](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/5e44a7f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ashland Springs Hotel Historic Downtown District 9.2/10 Wonderful (1000) "Historic property, perfectly located for Shakespeare Festival. " CA $244 CA $279 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Medford-Hotels-Ashland-Springs-Hotel.h660933.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/684defd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/a65795fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Queen Bed with Sofa bed (Courtyard) | Living area](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/30df7c7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed (Barbara Howard)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/815c2dcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winchester Inn Historic Downtown District 9.8/10 Exceptional (254) "Super comfortable room, great location to Main Street, excellent check in with friendly staff, would definitely stay here again!" CA $259 CA $306 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Medford-Hotels-Winchester-Inn.h1505812.Hotel-Information) ![Sundeck](https://images.trvl-media.com/lodging/16000000/15890000/15883900/15883819/c5a503ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/16000000/15890000/15883900/15883819/9d5a6193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family dining](https://images.trvl-media.com/lodging/16000000/15890000/15883900/15883819/eb8a3673.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/16000000/15890000/15883900/15883819/a628da48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rocky Point Resort Klamath Falls 8.2/10 Very good (382) "We really enjoyed our stay at Rocky Point. The room was comfortable and the area is beautiful. " CA $137 CA $155 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Klamath-Falls-Hotels-Rocky-Point-Resort.h15883819.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/77000000/76140000/76138500/76138485/b7be0ede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/77000000/76140000/76138500/76138485/1fc2d2f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/77000000/76140000/76138500/76138485/3521d653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/77000000/76140000/76138500/76138485/2f76930a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Compass by Margaritaville in Medford Medford 9.6/10 Exceptional (1002) "Great place to stay with our dog." CA $212 CA $256 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Medford-Hotels-Compass-By-Margaritaville-In-Medford.h76138485.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/19800/19703/8b20e842.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![42-inch LCD TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/20000/19800/19703/eebd3461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair salon](https://images.trvl-media.com/lodging/1000000/20000/19800/19703/ea36dd0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/20000/19800/19703/63c12e5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rogue Regency Inn and Suites Medford 9.0/10 Wonderful (2466) "Check in was great, overall a good place to stay " CA $151 CA $170 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Medford-Hotels-Rogue-Regency-Inn-And-Suites.h19703.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=2025-10-17&endDate=2025-10-18®ionId=6290&adults=2&amenities=BAR&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 "Excellent, especially for the price. The bed was super comfy, and the room was well-appointed and nicely decorated. We will return and tell our friends about Flagship." [](https://expedia.ca/Medford-Hotels-Flagship-Inn-Of-Ashland.h42817.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 "Great clean spacious rooms with a cool retro vibe" [](https://expedia.ca/Medford-Hotels-Ashland-Hills-Hotel-Suites.h28139.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 "My favorite place to stay in Ashland. Clean and nice rooms, affordable, PERFECT location and great staff! " [](https://expedia.ca/Medford-Hotels-The-Bards-Inn.h9249.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 "Comfortable room, very clean with everything we needed. Location was easy just off the I 5, with a really good Mexican restaurant within walking distance for dinner. We enjoyed our stay only one night. " [](https://expedia.ca/Medford-Hotels-Holiday-Inn-Express-Suites-Ashland.h845432.Hotel-Information) ![Ashland Springs Hotel](//images.trvl-media.com/lodging/1000000/670000/661000/660933/86190d91_y.jpg) ### Ashland Springs Hotel 10/10 Excellent "Second time staying at Ashland Springs. Came to the Oregon Shakespeare Festival for the weekend. Easy parking. Close to restaurants and shopping, very walkable. Great staff. Will be back again next year for sure!" [](https://expedia.ca/Medford-Hotels-Ashland-Springs-Hotel.h660933.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 "Staff were incredibly welcoming, and the room was very nice." [](https://expedia.ca/Medford-Hotels-Timbers-Motel.h915968.Hotel-Information) ![Plaza Inn & Suites at Ashland Creek](//images.trvl-media.com/lodging/1000000/890000/880600/880585/7e1c38a2_y.jpg) ### Plaza Inn & Suites at Ashland Creek 10/10 Excellent "Staff was great, cleaned room and left fresh towels, etc. everyday. Room was spacious. Great location. Great breakfast." [](https://expedia.ca/Medford-Hotels-Plaza-Inn-Suites-At-Ashland-Creek.h880585.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 "Very cool Windsor style architecture, spacious, pool, big breakfast space. Dog friendliest ever, complete with top sheet and biscuit for dog at check-in and two dog potty spots. 7 minutes drive from downtown Ashland and Saheksphere." [](https://expedia.ca/Medford-Hotels-Best-Western-Windsor-Inn.h2550.Hotel-Information) ![Callahan's Mountain Lodge](//images.trvl-media.com/lodging/13000000/12380000/12372400/12372363/2d34db80_y.jpg) ### Callahan's Mountain Lodge 10/10 Excellent "Lovely older lodge in beautiful setting. Nice rooms and great restaurant - excellent steak dinner! Felt very welcomed. Would definitely come back. " [](https://expedia.ca/Medford-Hotels-Callahans-Mountain-Lodge.h12372363.Hotel-Information) ## Frequently asked questions ### Searching for hotels with bars in Ashland? > If you'd like a place to stay where you can enjoy an evening cocktail after a day out and about, Ashland offers 315 hotels and other lodging options, including 5 accommodations with an onsite bar. While you're here, consider a visit to Allen Elizabethan Theatre and Oregon Shakespeare Festival. ### What are the best hotels with bars in Ashland? > Here are some of the top Ashland hotels with bars: [Ashland Hills Hotel & Suites](https://www.expedia.ca/Medford-Hotels-Ashland-Hills-Hotel-Suites.h28139.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. [Callahan's Mountain Lodge](https://www.expedia.ca/Medford-Hotels-Callahans-Mountain-Lodge.h12372363.Hotel-Information): Lodge with restaurant. Enjoy the bar, free breakfast, and free WiFi. [Ashland Springs Hotel](https://www.expedia.ca/Medford-Hotels-Ashland-Springs-Hotel.h660933.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. [Winchester Inn](https://www.expedia.ca/Medford-Hotels-Winchester-Inn.h1505812.Hotel-Information): Inn with restaurant. Enjoy the bar, free breakfast, and free WiFi. [Bayberry Inn and Retreat](https://www.expedia.ca/Ashland-Hotels-Bayberry-Inn-And-Retreat.h100723508.Hotel-Information): Property with restaurant. Enjoy the bar, free breakfast, and free WiFi. ### How many hotels with onsite bars will I be able to find in Ashland? > Expedia has 5 hotels with a bar in Ashland. ### What is there to do in Ashland? > If you have time to explore, consider visiting Allen Elizabethan Theatre, Oregon Shakespeare Festival, and Oregon Cabaret Theatre, and then find a cozy spot for a nightcap. Other places to see include Ashland Library and Lithia Park. Ashland is recognized for its entertainment choices, lively festivals, and top-notch restaurants. ### When is the best time to visit Ashland? > Visiting local bars in Ashland is more fun when you know what the weather holds. These temperatures and rainfall averages can help you decide the best time for bar hopping. 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. Average annual precipitation for Ashland is 33 inches. ### How can I get to Ashland and around the area? > You might want to make the most of these transportation options in and around Ashland: Fly into Rogue Valley Intl. Airport (MFR), which is located 14.4 mi (23.3 km) away from the city center. Otherwise, look for flights into Klamath Falls, OR (LMT-Klamath Falls Intl.), which is 49.7 mi (79.9 km) away. 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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 Bar in Ashland on Expedia.com](https://www.expedia.com/Ashland-Hotels-Bar-Hotel.0-0-d6290-tBarHotel.Travel-Guide-Filter-Hotels)