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      Air B and B Ashland Oregon: Top Vacation Rentals

      Exclusive deals on 6 top-rated Ashland vacation rentals near Lithia Park. Free parking, kitchens, pet-friendly, hot tubs. Book now!

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      Sat, 19 Sept
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      Rooms and Guests2 Guests, 1 room
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      Vacation rentals
      1-9 out of 9
      Sort by: high popularity
      • Price: low to high
      • Price: high to low
      • Guest rating: high to low
      • Popularity: high to low
      Swank House On Main St In AshlandHoliday home
      9.8
      Perfect5 total reviews
      our site & Booking.com
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      206 yd from City Center191 yd from Ashland Library
      Ice RinkFull KitchenCots
      • Two-bedroom home near theaters
      • On-site ice skating rink
      • Short walk to Shakespeare Festival
      FromUS$ 337 /nightSelect
      Bluemoon Vacation Rentals - Anne Hathaway HouseHoliday home
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      185 yd from City Center210 yd from Ashland Library
      Fully Equipped KitchenPrivate EntranceFree Private Parking
      • Eight bedrooms for large groups
      • Private entrance for extra privacy
      • Pet-friendly property with board games
      FromUS$ 530 /nightSelect
      Redtail Inn - 3 Suites Sleeps Up To 12Holiday home
      9.5
      Perfect19 total reviews
      our site & Booking.com
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      146 yd from City Center157 yd from Ashland Library
      Hot TubPet FriendlyFree Parking
      • Sleeps up to 12 guests
      • Private hot tub and patio
      • Pet-friendly with mountain views
      FromUS$ 223 /nightSelect
      The Heritage House At Second Street CottagesHoliday home
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      423 yd from City Center329 yd from Oregon Cabaret Theatre
      EV ChargingFull KitchenWashing Machine
      • Full kitchen in private cottage
      • On-site EV charging station
      • In-unit washing machine
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      The Mountain House By WanderlodgesHoliday home
      9.4
      Perfect37 total reviews
      our site & Booking.com
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      956 yd from City Center417 yd from Garfield Park
      Private ParkingFull KitchenNo Pets Allowed
      • Private parking included on-site
      • Spacious 3-bedroom holiday home
      • Fully equipped kitchen with dishwasher
      FromUS$ 254 /nightSelect
      Bluemoon Vacation Rentals - Bluemoon CottageHoliday home
      7.8
      Very good18 total reviews
      our site & Booking.com
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      1212 yd from City Center209 yd from Skateboard Park
      Private ParkingPicnic AreaFull Kitchen
      • Private cottage with full kitchen
      • Quiet street with private patio
      • Complimentary wine and chocolates
      FromUS$ 158 /nightSelect
      Pioneer Vacation Rentals - Pioneer North Suite Downtown AshlandHoliday home
      9.3
      Perfect14 total reviews
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      634 yd from City Center263 yd from Oregon Shakespeare Festival
      Private ParkingKitchenetteBalcony
      • Private parking on-site included
      • City views from private balcony
      • Walk-in shower in private bathroom
      FromUS$ 200 /nightSelect
      Hanna'S House By WanderlodgesHoliday home
      9.9
      Perfect13 total reviews
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      191 yd from City Center122 yd from Ashland Library
      Hot Spring BathWater SportsGarden View
      • On-site hot spring bath
      • Water sports facilities provided
      • Private garden view patio
      FromUS$ 151 /nightSelect
      Barclay Klum House By WanderlodgesApartment
      9.7
      Perfect17 total reviews
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      727 yd from City Center615 yd from Garfield Park
      Spa BathPrivate ParkingOutdoor Dining
      • Spa bath in private apartment
      • Garden-view balcony with dining
      • Full kitchen with dishwasher
      FromUS$ 209 /nightSelect

      Ashland, Oregon, offers a variety of vacation rentals ideal for theater enthusiasts and families. Properties like the Redtail Inn (rated 98/100) feature pet-friendly suites with private hot tubs and mountain views, while Hanna's House provides a hot spring bath and easy access to the Oregon Shakespeare Festival, just a 3-minute walk from the Ashland Library.

      Many rentals include fully equipped kitchens, free WiFi, and free parking, with options ranging from spacious holiday homes like The Mountain House by WanderLodges to budget-friendly Bluemoon Cottage. Central locations near Lithia Park and ScienceWorks Museum make these rentals convenient for exploring Ashland's cultural and outdoor attractions.