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Hotels of Earth

Winchester Inn

★★★★★ 35 South 2nd Street, Ashland, US

9.6 guest rating· 640 reviews

The five stars

Winchester Inn holds a five-star rating in its official classification, the requirement for every property in the Hotels of Earth collection.

The service side of those stars shows in its listing: Concierge service.

Guests score it 9.6/10 across 640 reviews.

About this hotel

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!

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Rooms & rates

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Comfort Triple Room with Shower

Sleeps 3 · 33 m² · Twin bed, Extra-large double bed (Super-king size)

  • Air conditioning
  • Single-room air conditioning for guest accommodation
  • Bathrobe
  • Private bathroom
  • Coffee/tea maker

This room features bathrobes, imported toiletries, and a hairdryer. This room is located on the main property.

Triple Room with Bath

Sleeps 3 · 33 m² · Twin bed, Extra-large double bed (Super-king size)

  • Air conditioning
  • Single-room air conditioning for guest accommodation
  • Bathrobe
  • Private bathroom
  • Coffee/tea maker

Along with a private entrance and patio, this room features bathrobes, imported toiletries, and a hairdryer. This room is located on the main property.

Two-Bedroom Suite

Sleeps 4 · 84 m² · Extra-large double bed (Super-king size), Queen bed, Sofa bed

  • Air conditioning
  • Single-room air conditioning for guest accommodation
  • Bathrobe
  • Private bathroom
  • Additional bathroom

Along with a sofa bed, private entrance, and patio, this suite features bathrobes, imported toiletries, and a hairdryer. This room is located on the main property.

Suite with Garden View

Sleeps 2 · 37 m² · Sofa bed, Queen bed

  • Desk
  • Air conditioning
  • Single-room air conditioning for guest accommodation
  • Bathrobe
  • Private bathroom

Along with a fireplace, spa bath, sofa bed, and private entrance, this suite features bathrobes, imported toiletries, and a hairdryer. This room is located on the main property.

Queen Suite

Sleeps 2 · 37 m² · Sofa bed, Queen bed

  • Air conditioning
  • Single-room air conditioning for guest accommodation
  • Bathrobe
  • Private bathroom
  • Coffee/tea maker

Along with a fireplace and private entrance, this room features bathrobes, imported toiletries, and a hairdryer. This room is located on the main property.

Deluxe King Suite

Sleeps 2 · 42 m² · Extra-large double bed (Super-king size)

  • Desk
  • Air conditioning
  • Single-room air conditioning for guest accommodation
  • Bathrobe
  • Private bathroom

Along with a fireplace and spa bath, this suite features bathrobes, imported toiletries, and a hairdryer. This room is located on the main property.

Double Room with Garden View

Sleeps 2 · 33 m² · Queen bed

  • Air conditioning
  • Single-room air conditioning for guest accommodation
  • Bathrobe
  • Private bathroom
  • Coffee/tea maker

This room features bathrobes, imported toiletries, and a hairdryer. This room is located on the main property.

King Room

Sleeps 2 · 33 m² · Extra-large double bed (Super-king size)

  • Air conditioning
  • Single-room air conditioning for guest accommodation
  • Bathrobe
  • Private bathroom
  • Coffee/tea maker

Along with a balcony, this room features bathrobes, imported toiletries, and a hairdryer. This room is located on the main property.

Standard Queen Room

Sleeps 2 · 28 m² · Queen bed

  • Desk
  • Air conditioning
  • Single-room air conditioning for guest accommodation
  • Bathrobe
  • Private bathroom

Along with a balcony, this room features bathrobes, imported toiletries, and a hairdryer. This room is located on the main property.

Family Suite

Sleeps 6 · 79 m² · Queen bed, Sofa bed, Extra-large double bed (Super-king size)

  • Air conditioning
  • Single-room air conditioning for guest accommodation
  • Bathrobe
  • Private bathroom
  • Additional bathroom

This spacious suite features 1 living room, 2 separate bedrooms and 1 bathroom with a walk-in shower and free toiletries. The air-conditioned suite features a flat-screen TV with cable channels, a private entrance, a minibar, a tea and coffee maker as well as city views. The unit has 3 beds.

Amenities

  • Free WiFi
  • Free Parking
  • Accessible parking
  • Breakfast takeaway containers
  • Restaurant
  • Bar
  • Air conditioning
  • Golf course
  • Non-smoking rooms
  • Non-smoking throughout
  • Family rooms
  • Allergy-free room
  • Cashless payment available
  • Cleaning standards that are effective against Coronavirus
Show all 47 amenities
  • Concierge service
  • Daily housekeeping
  • Delivered food - securely covered
  • Dry cleaning
  • Face masks for guests available
  • Facilities for disabled guests
  • Fax/photocopying
  • Fire extinguishers
  • Food delivered to guest room
  • Garden
  • Guest room sealed after cleaning
  • Guest rooms disinfected between stays
  • Guests can opt-out any cleaning services during stay
  • Hand sanitizer in guest room and key areas
  • Happy hour
  • Heating
  • Hiking
  • Invoice provided
  • Key access
  • Laundry washed per local authority guidelines
  • Luggage storage
  • Meeting/banquet facilities
  • Outdoor furniture
  • Physical distancing in dining areas
  • Physical distancing rules followed
  • Sanitized tableware & silverware
  • Shared stationery like menus, pens are removed
  • Smoke alarms
  • Special diet menus - on request
  • Staff adhere to local safety protocols
  • Tennis court
  • Themed dinner nights
  • Wine/champagne

Location

© OpenStreetMap contributors

35 South 2nd Street, Ashland, US

Check-in
from 04:00 PM
Check-out
until 11:00 AM

What guests say9.6640 reviews

+ Charming location+ Amazing breakfastOld building issuesStaff availability after hours
Cleanliness8.5
Service10.0
Location10.0
Room Quality9.4
Amenities9.5
Value for Money9.4

Lovely victorian-style inn close to the Ashland theatres.

9.0

This is a top-notch property in Ashland, we've visited multiple times before. It's close to the theatres. The breakfasts are very good. The furnishings are largely in an antique style.

The breakfast, while free, is full of premium offerings that are not. You are presented every day with a strangely computed bill (with a credit for a free breakfast) to which you are asked to add a tip. I would prefer being asked to add a cumulative tip at check-out. Rooms haven't been updated in a while.

Edward · IT · 2026-07-24

Very pleasant stay in a very comfortable room; very attentive staff.

10.0

Nicely served breakfast ordered from a menu. Wait staff was excellent. Didn't expect the $5 charge for the coffee at breakfast.

Although it was not an issue for me, I would advise anyone that has mobility issues that there are stairs and hills on the property (no elevator).

Nina · US · 2026-07-22

Beautiful stay in the heart of it all

10.0

Great location and staff. Comfortable room and amazing breakfast. They even left ice and a treat in the afternoon, which made a huge difference.

Marianne · US · 2026-07-16

Hotels of Earth · questions

Is Winchester Inn really a five-star hotel?
Yes. Its own classification data carries five stars; that rating, not a style label, is what puts a property in this collection.

Good to know

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.

A deposit may be required at the property.