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Located in Ashland, a 2-minute walk from Oregon Cabaret Theatre, Winchester Inn has accommodations with a garden, free private parking, a restaurant and a bar. Among the facilities at this property are a concierge service and luggage storage space, along with free WiFi throughout the property. Certain accommodations at the property have a balcony with a mountain view. The rooms come with air conditioning, a flat-screen TV with cable channels, a fridge, a coffee machine, a shower, free toiletries and a closet. Rooms have a private bathroom with a hairdryer, while certain rooms come with a terrace and others also feature city views. The rooms in the hotel are equipped with bathrobes and an iPod docking station. Breakfast is available each morning, and includes à la carte, Full English/Irish and American options. You can play tennis at Winchester Inn, and the area is popular for hiking. Popular points of interest near the accommodation include Ashland Library, Oregon Shakespeare Festival and Southern Oregon University. Rogue Valley International-Medford Airport is 24 miles from the property.

Couples in particular like the location – they rated it 9.8 for a two-person trip.

Distance in property description is calculated using © OpenStreetMap

Property highlights

Top Location: Highly rated by recent guests (9.8)

Breakfast Info

Full English/Irish, American, Breakfast to go

Free private parking available at the hotel


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Availability

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Room Type
Number of guests
 
1 twin bed
and
1 king bed
1 twin bed
and
1 king bed
Bedroom 1
1 queen bed
Bedroom 2
1 king bed
Living room
1 sofa bed
1 sofa bed
and
1 queen bed
1 king bed
Bedroom
1 king bed
Living room
1 sofa bed
Bedroom
1 king bed
Living room
1 sofa bed
1 king bed
1 sofa bed
and
1 queen bed
Bedroom
1 queen bed
Living room
1 sofa bed
1 king bed
1 king bed
1 queen bed
1 sofa bed
and
1 queen bed
1 king bed
1 queen bed
1 king bed
1 king bed
and
1 sofa bed
1 king bed
1 queen bed
1 king bed
and
1 sofa bed
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Guest reviews

Categories:

Staff
9.8
Facilities
9.5
Cleanliness
9.7
Comfort
9.6
Value for money
9.1
Location
9.8
Free Wifi
8.8
High score for Ashland

Select topics to read reviews:

Guests who stayed here loved

  • Jill
    United States of America United States of America
    I loved the old time charm and that is was walkable to everything!
  • Lan
    China China
    I really enjoyed my time in Ashland. The city’s twinkling lights on rooftops during the winter nights create a warm and cozy atmosphere. Staying at the Winchester Inn for two days was a delightful surprise. The hotel has a charming, vintage...
  • Catherine
    United States of America United States of America
    (See google reviews for pictures with this review) Queen Anne room is lovely. Comfy king bed and a twin. Tall windows facing north. Coffee maker and tea kettle and good size mini fridge. Fabulous breakfast and accommodating of dietary...
  • Glynnis
    United States of America United States of America
    Wonderful staff, great bar and restaurant. Delicious breakfast
  • Greg
    Canada Canada
    Everything, excellent location downtown yet quiet. The room was unique, well appointed and so comfortable. The staff are very nice and attending. We even got a call asking when we would arrive so that they could greet us. The restaurant was first...
  • Pamela
    United States of America United States of America
    Everything and Everyone. Fantastic stay. Fantastic food. Fantastic staff. Absolutely wonderful. 10 out of 10
  • Douglas
    United States of America United States of America
    Beautiful, comfortable and historic Inn in an amazing town!
  • Maria
    United States of America United States of America
    very cozy, clean and helpful staff. had a lovely time.
  • Dan
    United States of America United States of America
    Our room was wonderful! We stayed in the Patio room with easy access and just a short walk from downtown.
  • Regina
    United States of America United States of America
    We wanted a romantic getaway and that is exactly what we received! Our room was spectacular and the soft robes added the special something. We plan to make this an annual trip!

Hotel area info

Restaurants
2 Restaurants On Site

  • Alchemy Restaurant and Bar
    • Cuisine
      American • French • Local • International
    • Ambience
      Modern • Romantic
    • Dietary options
      Vegetarian • Gluten-free • Dairy-free
  • Chateaubriand 36
    • Cuisine
      French • Steakhouse
    • Open for
      Dinner
    • Ambience
      Family-friendly

Amenities of Winchester Inn
Great facilities! Review score, 9.5

Most popular amenities

  • Free parking
  • Free Wifi
  • Non-smoking rooms
  • 2 restaurants
  • Facilities for disabled guests
  • Family rooms
  • Tea/Coffee Maker in All Rooms
  • Bar

Bathroom

  • Toilet paper
  • Towels
  • Bathtub or shower
  • Private bathroom
  • Toilet
  • Free toiletries
  • Bathrobe
  • Hairdryer
  • Shower

Bedroom

  • Linens
  • Wardrobe or closet
  • Alarm clock
  • Extra long beds (> 6.5 ft)

View

  • View

Outdoors

  • Outdoor furniture
  • Garden

Kitchen

  • Coffee machine
  • Electric kettle
  • Refrigerator

Room Amenities

  • Socket near the bed
  • Clothes rack

Activities

  • Happy hour
    Additional charge
  • Themed dinners
    Additional charge
  • Hiking
    Off-site
  • Golf course (within 2 miles)
    Additional charge
  • Tennis court
    Off-site

Living Area

  • Sitting area

Media & Technology

  • iPod dock
  • Flat-screen TV
  • Cable channels
  • Video
  • Radio
  • TV

Food & Drink

  • Wine/Champagne
    Additional charge
  • Special diet meals (on request)
  • Bar
  • Minibar
  • Tea/Coffee maker

Internet
Wifi is available in all areas and is free of charge.

Parking
Free private parking is available on site (reservation is not needed).

  • Street parking
  • Accessible parking

Services

  • Daily housekeeping
  • Concierge
  • Baggage storage
  • Fax/Photocopying
    Additional charge
  • Dry cleaning
    Additional charge
  • Wake-up service/Alarm clock
  • Meeting/Banquet facilities
    Additional charge

Front Desk Services

  • Invoice provided

Safety & security

  • Fire extinguishers
  • Smoke alarms
  • Key access

General

  • Carbon monoxide detector
  • Air conditioning
  • Smoke-free property
  • Hypoallergenic room available
  • Heating
  • Carpeted
  • Family rooms
  • Ironing facilities
  • Facilities for disabled guests
  • Non-smoking rooms
  • Iron

Languages Spoken

  • English

House rules
Winchester Inn takes special requests – add in the next step!

Check-in
From 4:00 PM
Guests are required to show a photo ID and credit card at check-in.
You need to let the property know what time you'll be arriving in advance.
Check-out
Until 11:00 AM
Cancellation/ prepayment
Cancellation and prepayment policies vary according to accommodation type. Enter your stay dates and check the conditions of your selected option.
Refundable damage deposit
A damage deposit of $250 is required on arrival. This will be collected by credit card. You should be reimbursed on check-out. Your deposit will be refunded in full by credit card, subject to an inspection of the property.
Children & Beds

Child policies

Children of all ages are welcome.

Children 9 and above will be charged as adults at this property.

To see correct prices and occupancy info, add the number and ages of children in your group to your search.

Crib and extra bed policies

0 - 2 years
Extra bed upon request
Free
Crib upon request
Free
3 - 8 years
Extra bed upon request
Free
9+ years
Extra bed upon request
$45 per person, per night

Prices for cribs and extra beds aren't included in the total price. They'll have to be paid for separately during your stay.

The number of extra beds and cribs allowed depends on the option you choose. Check your selected option for more info.

All cribs and extra beds are subject to availability.

No age restriction
There's no age requirement for check-in
Pets
Pets are not allowed.
Cards accepted at this hotel
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The fine print
Must-know information for guests at this property

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 Winchester Inn 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.

In response to the coronavirus (COVID-19), additional safety and sanitation measures are in effect at this property.

A damage deposit of $250 is required on arrival. This will be collected by credit card. You should be reimbursed on check-out. Your deposit will be refunded in full by credit card, subject to an inspection of the property.

FAQs about Winchester Inn

  • Check-in at Winchester Inn is from 4:00 PM, and check-out is until 11:00 AM.

  • Room options at Winchester Inn include:

    • Triple
    • Suite
    • Double
    • Family
  • Winchester Inn offers the following activities/services (charges may apply):

    • Hiking
    • Tennis court
    • Golf course (within 2 miles)
    • Themed dinners
    • Happy hour
  • Winchester Inn has 2 restaurants:

    • Chateaubriand 36
    • Alchemy Restaurant and Bar
  • Guests staying at Winchester Inn can enjoy a highly-rated breakfast during their stay (guest review score: 9.4).

    Breakfast option(s) include:

    • Full English/Irish
    • American
    • À la carte
    • Breakfast to go
  • Winchester Inn is 1,300 feet from the center of Ashland. All distances are measured in straight lines. Actual travel distances may vary.

  • The prices at Winchester Inn may vary depending on your stay (e.g. dates, hotel's policy etc.). To see prices, enter your dates.