How payments to us affect ranking

How payments to us affect ranking

See prices from 9 sites
from$184
See prices from 9 sites
from$184
  • Exterior
  • bedroom
  • bathroom

1 / 99

Good to know

  • Sister French-inspired steakhouse

    Indulge in a French-inspired steakhouse experience at Chateaubriand 36, the inn's sister restaurant, offering an inviting atmosphere.

  • Award-winning Alchemy Restaurant and Bar

    Savor exceptional dining at Alchemy, featuring an award-winning wine list recognized by Wine Spectator’s Best of Award of Excellence since 2015.

  • Historic Victorian architecture

    Immerse yourself in the charm of a beautifully maintained Victorian house and carriage house, offering a unique blend of historic elegance and modern updates.

  • Proximity to Oregon Shakespeare Festival

    Experience unparalleled access to culture, located just two blocks or a short walk from the renowned Oregon Shakespeare Festival theaters.

  • Unique room configurations

    Choose from individually designed rooms, including options with balconies, fireplaces, whirlpool tubs, or the spacious two-bedroom Duet unit with a kitchenette.

  • Personalized welcome amenities

    Discover thoughtful touches like daily delivered cookies or chocolate caramels, a personalized welcome card, and fresh flowers in your room.

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 9 sites
from$184

Similar stays

    • Free WiFi
    • Pool
    • Spa
    See prices from 14 sites
    from$74

    • Free WiFi
    • Pool
    • Spa
    See prices from 13 sites
    from$115

    • Free WiFi
    • Pool
    • Parking
    See prices from 14 sites
    from$139

    • Free WiFi
    • Spa
    • Parking
    See prices from 12 sites
    from$131

    • Free WiFi
    • Pool
    • Parking
    See prices from 13 sites
    from$50

    • Free WiFi
    • Parking
    • Pets
    See prices from 4 sites
    from$175

    • Free WiFi
    • Parking
    • A/C
    See prices from 9 sites
    from$158

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

    • Free WiFi
    • Parking
    • Pets
    See prices from 1 site
    from$129

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

Price trend

Based on lowest prices on trivago from the last 30 days
$519
$260
$0

Tue, 10/27/26

$258

Wed, 10/28/26

$206

Thu, 10/29/26

$284

Fri, 10/30/26

$344

Sat, 10/31/26

$355

Sun, 11/01/26

$272

Mon, 11/02/26

N/A

Tue, 11/03/26

N/A

Wed, 11/04/26

N/A

Thu, 11/05/26

$239

Fri, 11/06/26

$312

Sat, 11/07/26

$339

Sun, 11/08/26

N/A

Mon, 11/09/26

$206

Tue, 11/10/26

$263

Wed, 11/11/26

$244

Thu, 11/12/26

$245

Fri, 11/13/26

$323

Sat, 11/14/26

$519

Sun, 11/15/26

N/A

Mon, 11/16/26

$229

Tue, 11/17/26

$284

Wed, 11/18/26

$241

Thu, 11/19/26

$290

Fri, 11/20/26

N/A

Sat, 11/21/26

$306

Sun, 11/22/26

$264

Mon, 11/23/26

$196

Tue, 11/24/26

N/A

Wed, 11/25/26

$295

Thu, 11/26/26

N/A

Fri, 11/27/26

$350

Sat, 11/28/26

$352

Sun, 11/29/26

$288

Mon, 11/30/26

N/A

Tue, 12/01/26

N/A

Wed, 12/02/26

N/A

Thu, 12/03/26

N/A

Fri, 12/04/26

$311

Sat, 12/05/26

$342

Sun, 12/06/26

$260

Mon, 12/07/26

N/A

Tue, 12/08/26

N/A

Wed, 12/09/26

$268

Thu, 12/10/26

N/A

Fri, 12/11/26

N/A

Sat, 12/12/26

N/A

Reviews

9.5
Excellent
based on 1,258 ratings from top 
sites
sites

Review summary

Summarized by AI from 600+ reviews

This charming hotel, a tranquil historic hideaway, caters to couples, sightseers, and luxury travelers seeking a refined and relaxing experience. Its excellent central location in Ashland places guests within easy walking distance of the Oregon Shakespeare Festival, Lithia Park, and numerous shops and restaurants. The hotel's standout amenity is its gourmet two-course complimentary breakfast, featuring diverse hot entrees and gluten-free options. Guests consistently praise the staff's exceptional friendliness and attentiveness, contributing to a pampered stay. For an enhanced experience, consider booking one of the separate units like "The Duet" or a two-bedroom cottage for added space and convenience.

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. Bathrobe

Location

35 South Second Street, Ashland, 97520, USA

Highlight

Proximity to Oregon Shakespeare Festival

Experience unparalleled access to culture, located just two blocks or a short walk from the renowned Oregon Shakespeare Festival theaters.

Distance from Winchester Inn

  1. 0.2 km from Ashland (City centre)
  2. 0.2 km from Ashland Downtown Historic District
  3. 0.3 km from Allen Elizabethan Theatre
  4. 0.3 km from Angus Bowmer Theatre
  5. 0.3 km from Green Show
  6. 0.4 km from Ashland Railroad Addition Historic District
  7. 0.8 km from Lithia Park
  8. 0.9 km from Skidmore Academy Historic District
  9. 19.1 km from South Oakdale Historic District
  10. 19.7 km from Craterian Ginger Rogers Theater
  11. 23.9 km from Rogue Valley International-Medford Airport
  12. 77.5 km from Klamath Falls

Explore nearby attractions

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.

Among Top Rated Hotels in Ashland

  • The Peerless Hotel
    See prices from 9 sites
    from$158
  • Country Willows Inn
    Select dates to see exact prices
  • Little House
    Select dates to see exact prices
  • Abigail's Bed and Breakfast Inn
    Select dates to see exact prices
  • The Iris Inn
    Select dates to see exact prices
  • Ashland Valley Inn
    Select dates to see exact prices
  • Chanticleer Inn
    Select dates to see exact prices
  • Super 8 Ashland
    Select dates to see exact prices

Other stays in Ashland

Popular hotel categories in Ashland

Destinations near Winchester Inn

See all stays in Ashland