5 Star Hotels in Ashland, Oregon

Compare 2 top-rated 5-star hotels in Ashland, OR near Shakespeare Festival & Lithia Park. Free breakfast, parking, and concierge. Book now!

Check-in
Thu, 24 Sept
Check-out
Fri, 25 Sept
Rooms and Guests2 Guests, 1 room
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Check-in
Thu, 24 Sept
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Check-out
Fri, 25 Sept
Rooms and Guests2 Guests, 1 room
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Check-in
Thu, 24 Sept
-
Check-out
Fri, 25 Sept
Rooms and Guests2 Guests, 1 room
2Filter & Sort
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8.4
Great660 total reviews
our site & Booking.com
Map
2.7 mi from City Center
Indoor PoolHot TubFitness Center
  • 24-hour pool and hot tub
  • Pet-friendly up to 3 pets
  • Free breakfast with waffle bar
FromUS$ 93 /nightSelect
9.3
Perfect456 total reviews
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294 yd from City Center102 yd from Oregon Cabaret Theatre
Private ParkingOn-site RestaurantHistoric Garden
  • Award-winning Alchemy Restaurant
  • Historic inn with romantic gardens
  • Two-course gourmet breakfast included
FromUS$ 220 /nightSelect
9.6
Perfect67 total reviews
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741 yd from City Center254 yd from Oregon Shakespeare Festival
Sun TerraceGardenPrivate Parking
  • Historic Victorian mansion (1883)
  • Gourmet breakfast with dietary options
  • Communal dining fosters guest connections
FromUS$ 288 /nightSelect
10.0
Perfect70 total reviews
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1692 yd from City Center852 yd from Skateboard Park
Gourmet BreakfastAdults OnlyOutdoor Gardens
  • Gourmet two-course breakfast daily
  • Theater bags with cushions provided
  • Homemade snacks available 24/7
FromUS$ 335 /nightSelect

Ashland, Oregon, offers a curated selection of 5-star hotels, each providing a distinct level of luxury. These properties cater to discerning travelers seeking exceptional service, prime locations, and unique atmospheres. Expect to invest in a premium stay, with rates reflecting the high standard of amenities and personalized attention. The most sought-after accommodations are near the Oregon Shakespeare Festival and Lithia Park, placing you steps from cultural attractions and outdoor recreation. For a truly exceptional experience, consider the McCall House Boutique Hotel, which boasts a perfect guest score of 100 and offers a sun terrace, garden, concierge service, and a gourmet breakfast with champagne. Alternatively, the Abigail's Bed and Breakfast Inn provides a 5-star adults-only retreat with elegant rooms, a beautiful garden, and free WiFi, also within walking distance of the festival.

Both the McCall House and Abigail's are within a short walk of the Oregon Shakespeare Festival and Lithia Park, making them ideal for culture and nature lovers. The Winchester Inn, another top choice, offers a historic setting, a garden, tennis court, and a restaurant serving French and American cuisine. Amenities across these hotels include free WiFi, private parking, and gourmet breakfast options catering to various dietary needs. For a seamless experience, book directly with the hotel or use a trusted booking platform to secure the best rates. With only a handful of true 5-star options, early reservation is recommended, especially during the summer festival season. Whether you're visiting for a romantic getaway or a cultural immersion, Ashland's 5-star hotels provide an unforgettable base for your Oregon adventure.