How payments to us affect ranking

How payments to us affect ranking

See prices from 8 sites
from£167
See prices from 8 sites
from£167
  • Exterior
  • Bedroom
  • Bathroom

1 / 99

Good to know

  • Fine dining at Alchemy Restaurant

    Enjoy award-winning wine and French-inspired cuisine at the on-site Alchemy Restaurant and Bar.

  • Premium bedding and room amenities

    Relax in rooms featuring high thread count sheets, Egyptian cotton towels, and daily delivered treats.

  • Second floor access without elevator

    Guest rooms located on the second floor require the use of stairs as the property lacks an elevator.

  • Prime location near Shakespeare Festival

    Walk just four minutes to reach the Oregon Shakespeare Festival and downtown Ashland attractions.

  • Potential noise from HVAC units

    Some guest rooms feature heating and cooling units that may produce audible noise during operation.

This summary was created by AI and might not be 100% accurate.

Rooms

  • Suite, 1 King Bed with Sofa bed (Robert Gordon)

    • 1 1 King Bed and 1 Double Sofa Bed
    • Sleeps 2
    • 500 sq ft

  • Double Room, 1 Queen Bed (Patio)

    • 1 1 Queen Bed
    • Sleeps 2
    • 350 sq ft

  • Suite, 1 King Bed (Hargadine)

    • 1 1 King Bed
    • Sleeps 2
    • 900 sq ft

  • Double Room, 1 Queen Bed (Catharine M)

    • 1 1 Queen Bed
    • Sleeps 2
    • 300 sq ft

Compare with similar stays

Selected stay

  • Free WiFi
  • Parking
  • A/C
See prices from 8 sites
from£167

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    • Free WiFi
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    Select dates to see exact prices

    • Free WiFi
    • Parking
    • Pets
    Select dates to see exact prices

    • Free WiFi
    • Parking
    • A/C
    Select dates to see exact prices

    • Parking
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    • Free WiFi
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    • Free WiFi
    • Spa
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Price trend

Based on lowest prices on trivago from the last 30 days
£330
£165
£0

Tue, 20/10/26

£230

Wed, 21/10/26

£247

Thu, 22/10/26

£230

Fri, 23/10/26

£330

Sat, 24/10/26

£291

Sun, 25/10/26

£236

Mon, 26/10/26

£122

Tue, 27/10/26

£126

Wed, 28/10/26

£143

Thu, 29/10/26

£147

Fri, 30/10/26

N/A

Sat, 31/10/26

£165

Sun, 01/11/26

£143

Mon, 02/11/26

N/A

Tue, 03/11/26

N/A

Wed, 04/11/26

N/A

Thu, 05/11/26

N/A

Fri, 06/11/26

£167

Sat, 07/11/26

£164

Sun, 08/11/26

N/A

Mon, 09/11/26

N/A

Tue, 10/11/26

£161

Wed, 11/11/26

N/A

Thu, 12/11/26

£157

Fri, 13/11/26

N/A

Sat, 14/11/26

N/A

Sun, 15/11/26

N/A

Mon, 16/11/26

N/A

Tue, 17/11/26

£159

Wed, 18/11/26

N/A

Thu, 19/11/26

N/A

Fri, 20/11/26

N/A

Sat, 21/11/26

N/A

Sun, 22/11/26

N/A

Mon, 23/11/26

N/A

Tue, 24/11/26

£141

Wed, 25/11/26

N/A

Thu, 26/11/26

N/A

Fri, 27/11/26

N/A

Sat, 28/11/26

N/A

Sun, 29/11/26

N/A

Mon, 30/11/26

N/A

Tue, 01/12/26

N/A

Wed, 02/12/26

N/A

Thu, 03/12/26

N/A

Fri, 04/12/26

N/A

Sat, 05/12/26

N/A

Sun, 06/12/26

N/A

Mon, 07/12/26

N/A

Tue, 08/12/26

N/A

Wed, 09/12/26

N/A

Thu, 10/12/26

N/A

Fri, 11/12/26

N/A

Sat, 12/12/26

N/A

Sun, 13/12/26

N/A

Mon, 14/12/26

N/A

Tue, 15/12/26

N/A

Wed, 16/12/26

N/A

Thu, 17/12/26

N/A

Fri, 18/12/26

N/A

Sat, 19/12/26

N/A

Sun, 20/12/26

N/A

Reviews

9.5
Excellent
based on 1,257 ratings from top 
sites
sites

Review summary

Summarized by AI from 600+ reviews

A charming historic retreat for culture-seeking travelers.


This property serves as a refined sanctuary for couples and sightseers who appreciate historic charm and attentive service. The hotel sits in the heart of historic downtown Ashland, pairing its prime location with beautifully maintained grounds that offer a tranquil outdoor escape. Guests consistently praise the gourmet breakfast for its sophisticated, made-to-order quality, and those seeking extra space should consider booking the well-equipped carriage house for a more private experience.


Some guests mentioned: limited parking, noisy climate control, stairs required.

Rated above average for Ashland

Guest reviews

Excellent85%
Very good11%
Good2%
Fair2%
Poor0%

Top amenities

  • WiFi in lobby
  • WiFi in rooms
  • Parking
  • A/C
  • Restaurant
  • Hotel bar

All amenities

Property amenities

  1. Business centre
  2. Parking
  3. Terrace
  4. Bar

Room amenities

  1. Shower
  2. Ironing board
  3. Openable windows
  4. Television

Sports facilities

  1. Golf course
  2. Hiking trail

Hotel characteristics

  1. Family friendly
  2. LGBTQ+ friendly

Accessibility

  1. Accessible travel path
  2. Accessible parking

Wellness

  1. Dressing gown

Location

35 South Second Street, Ashland, 97520, USA

Distance from Winchester Inn

Ashland:0.1 miles

Ashland Downtown Historic District:0.1 miles

Allen Elizabethan Theatre:0.2 miles

Angus Bowmer Theatre:0.2 miles

Green Show:0.2 miles

Ashland Railroad Addition Historic District:0.3 miles

Lithia Park:0.5 miles

Skidmore Academy Historic District:0.5 miles

South Oakdale Historic District:11.8 miles

Craterian Ginger Rogers Theater:12.2 miles

Rogue Valley International-Medford Airport:14.9 miles

Klamath Falls:48.2 miles

Property info

35 South Second Street, Ashland, 97520, USA

Frequently Asked Questions about Winchester Inn

  • Is there a pool area at Winchester Inn?

    No, Winchester Inn doesn’t offer pool areas.

  • Are pets allowed at Winchester Inn?

    No, Winchester Inn doesn’t allow pets.

  • Is parking available at Winchester Inn?

    Yes, Winchester Inn provides Parking, Accessible parking for guests.

  • What time is check-in and check-out at Winchester Inn?

    Check-in at Winchester Inn is available from: . Check-out time is by .

  • Where is Winchester Inn located?

    Winchester Inn is located in 35 South Second Street, 97520, Ashland, USA.

The prices and availability we receive from booking sites change constantly. This means you may not always find the exact same offer you saw on trivago when you land on the booking site.

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