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Winchester Inn

9.6/10659 reviewsAshland

Luxurious Accommodations Winchester Inn, located just 300 metres from the Oregon Shakespeare Festival, offers elegantly appointed rooms with 600 thread count sheets, down feather bedding, and private balconies or patios. The rooms are equipped with modern amenities including flat-screen TVs and air conditioning, ensuring a comfortable stay for all guests. Gourmet Dining Experience Guests at Winchester Inn can indulge in a 2-course gourmet breakfast included in their stay, prepared with fresh ingredients. The on-site bar and restaurant with an outdoor patio offer a perfect setting to unwind and enjoy delicious meals. Additionally, a coffee bar is available for guests to grab a quick pick-me-up throughout the day. Concierge Service and Convenience The hotel provides concierge service to assist guests with any inquiries or bookings, ensuring a seamless and enjoyable stay. With free parking on-site and proximity to Southern Oregon University and Rogue Valley Airport, Winchester Inn offers convenience and accessibility for all travelers. Book your stay at Winchester Inn now for a luxurious and memorable experience!

What this place offers

  • WiFi available
  • Free WiFi
  • Parking
  • Free Parking
  • Non-smoking rooms
  • Air conditioning

Policies & house rules

  • Check-in from 16:00
  • Check-out until 11:00
  • Children welcome
  • Free parking

Guests are required to show a photo ID and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply. Please inform of your expected arrival time in advance. You can use the Special Requests box when booking, or contact the property directly using the contact details in your confirmation. Managed by a private host A deposit may be required at the property.

Suitely partner stays nearby

Ashland Hotel w/Gym, pool, Ashland, OR

Ashland, OR
Free cancellationSuitely partner

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659 reviews

Guests liked

  • Charming location
  • Amazing breakfast

Guests mentioned

  • Old building issues
  • Staff availability after hours

  • Christey

    US · couple · Oct 2026

    10/10

  • Markuw1969

    NL · couple · Oct 2026

    8/10

    Leuke en romantische plek!

    Leuke plek met leuke uitstraling. Tja, ze hebben het daar goed voor elkaar met restaurant van hoe kwaliteit en aan de overkant ook nog eens een franse bistro volgens mij in eigendom ook. Duidelijk in de hogere prijsklasse en wij konden via Booking een lagere prijs krijgen dan rechtstreeks.

    Niets

  • Nuray

    US · couple · Oct 2026

    9/10

    Charming hotel in a great location.

    Lovely property, very close to the OSF, maybe a 7 minute walk. Close to restaurants and other shops downtown. The staff was helpful! The room was huge, with a separate sitting area, the bathroom had a large whirlpool tub and a walk in shower! Breakfast was always delicious and our severs were so friendly!

    Some stains on the floors and some of the decorative pillows. But honestly not a huge deal. I would recommend bringing some disposable slippers! The stairs were a little daunting as we were in and out of our room several times a days! But overall very minor issues!

  • Paul

    US · couple · Sep 2026

    2/10

    I found the staff to be less than forthwright, and even deceiving in the information they provided. If you choose to stay here becareful of what the staff tells you.

  • Corey

    US · solo_traveller · Sep 2026

    9/10

Location

35 S. 2nd St. · Ashland