Winchester Inn

Winchester Inn

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Winchester Inn

Ashland - 35 S. 2Nd St., See map

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Why do I recommend this accommodation?

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Very popular destination!

8 properties have been booked in the last 15 minutes in Ashland - Or

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Tourism surcharge from per person per night not included in the final booking price ( payable at the hotel)

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Latest reviews of the property

9,4 Excellent
Rating 4,7 around 5 for travellers of Tripadvisor

Excellent

Based on 326 reviews

Rating 4,9 around 5 for travellers of Tripadvisor

Location

Rating 4,8 around 5 for travellers of Tripadvisor

Quiet in the room

Rating 4,8 around 5 for travellers of Tripadvisor

Rooms

Rating 4,8 around 5 for travellers of Tripadvisor

Service

Rating 4,5 around 5 for travellers of Tripadvisor

Value for money

Rating 4,9 around 5 for travellers of Tripadvisor

Cleanliness

This accommodation stands out for being in the heart of Ashland

Showing 4 featured reviews out of 326 TripAdvisor reviews

D

Danielle B

30/03/2026

Rating 5 around 5 for travellers of Tripadvisor

“Charming!”

We stayed in the Mapleview Suite across the road from the main building & had a lovely stay from check in to check out! The complementary breakfast was absolutely delicious, staff were wonderful & the Inn & garden were charming. We are from the UK and it really reminded us of a B&B back home!

J

Jeff J

26/03/2026

Rating 5 around 5 for travellers of Tripadvisor

“Exceptional”

Wonderful setting, excellent and personal service, exceptional value, couldn't be better.

L

Linda L

22/03/2026

Rating 5 around 5 for travellers of Tripadvisor

“Where the Ashland experience has a rooted home with a community of support”

I don't normally post, but we (husband/self) LOVE this place SO much that I broke my mute-social media rule of not putting me out there/posting. Does 3-5 times staying from out of town each year count for being a fan? I think so. We have stayed at a variety of other GREAT Ashland places (there are … more

B

B G

04/03/2026

Rating 5 around 5 for travellers of Tripadvisor

“Charming in Every Way!”

I recently enjoyed a two night stay in the Belvedere Suite and it was delightful! The house and grounds are charming, immaculate and obviously well cared for. The inn keepers and team at the Winchester provided impeccable service and with such warmth and genuine kindness. My stay inspired me to … more

The reviews shown have not been verified. Viajes El Corte Inglés, S.A. does not guarantee that they correspond to real users of the service nor does it assume responsibility for their content. More Info

About the property

Description

Take in the views from a terrace and a garden and make use of amenities such as complimentary wireless internet access. Additional amenities at this Victorian inn include concierge services and gift shops/newsstands.. Featured amenities include complimentary newspapers in the lobby, dry cleaning/laundry services, and luggage storage. Free self parking is available onsite..

How to arrive

Ashland - See map

A stay at Winchester Inn places you in the heart of Ashland, steps from Oregon Cabaret Theatre and 3 minutes by foot from Ashland Library. This inn is 0.2 mi (0.3 km) from Lithia Park and 0.2 mi (0.3 km) from Oregon Shakespeare Festival.. Distances are displayed to the nearest 0.1 mile and kilometer. Oregon Cabaret Theatre - 0.2 km / 0.1 mi Ashland Library - 0.3 km / 0.2 mi Lithia Park - 0.3 km / 0.2 mi Oregon Shakespeare Festival - 0.3 km / 0.2 mi Thomas Theatre - 0.4 km / 0.2 mi Angus Bowmer Theatre - 0.4 km / 0.2 mi Allen Elizabethan Theatre - 0.4 km / 0.2 mi Ashland Creek - 0.5 km / 0.3 mi Southern Oregon University - 1.4 km / 0.8 mi North Mountain Park - 2 km / 1.3 mi Schneider Museum of Art - 2.2 km / 1.4 mi ScienceWorks Hands-On Museum - 2.4 km / 1.5 mi Ashland Dog Park - 2.5 km / 1.5 mi Weisinger Family Winery - 5.4 km / 3.4 mi Grizzly Peak Winery - 5.8 km / 3.6 mi The preferred airport for Winchester Inn is Rogue Valley Intl. Airport (MFR) - 25.3 km / 15.7 mi . In Ashland (Historic Downtown District).

Facilities and services

At Winchester Inn, enjoy a satisfying meal at the restaurant. Quench your thirst with your favorite drink at the bar/lounge. A complimentary cooked-to-order breakfast is served daily from 8 AM to 9:30 AM..

Other
Air conditioning
Heating (free of charge)
Additional services
Dry cleaning service
Laundry Service
Lift
Maid
Reception
Concierge service
Reception
Entertainment
Shops in hotel
Parking
Nearby parking
Pets
No pets allowed
Smoking
Smoking not allowed
Wi-Fi
Complimentary Wi-Fi
High-speed cable connection
Services
Café
Fan
Garden
Hair dryer
Iron
Luggage storage
Meeting room
Newspapers
Sale of tickets
Terrace
Bars
Bar
Restaurants
Breakfast buffet
Accessibility
Lift with braille
Wheelchair access
Check-in/Check-out
Deposit:
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General
Number of people: #{numberOfPersons}
Floor: #{floorNumber}
Tourism register number:
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Our rentals include:
Utilities
Cleaning
Admin fees and taxes
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Good to know

About the deposit

Some accommodation providers may require a deposit, which is not included in the price. This deposit will be payable upon arrival and refunded in full upon departure, provided that no damage has been caused.

Additional information

Key pick-up

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Taxes included in the final price

This property has additional information that you can

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Frequently asked questions about Winchester Inn

  • Which services stand out at Winchester Inn?

    Featured services at Winchester Inn are: Air conditioning, Heating (free of charge), Fan, Laundry Service See full list of services at Winchester Inn.
  • Yes, at Winchester Inn you´ll find Restaurant, Breakfast buffet.
  • Yes, the Winchester Inn has Nearby parking.
  • Yes, guests at Winchester Inn will be able to enjoy High-speed cable connection, Complimentary Wi-Fi.
  • Yes, check-in at Winchester Inn is from 4.00 pm and check-out is by 11.00 am.
  • The top reviews of Winchester Inn are: We stayed in the Mapleview Suite across the road from the main building & had a lovely stay from check in to check out! The complementary breakfast was absolutely delicious, staff were wonderful & the Inn & garden were charming. We are from the UK and it really reminded us of a B&B back home!.
  • This is the information we have about the surroundings of Winchester Inn: A stay at Winchester Inn places you in the heart of Ashland, steps from Oregon Cabaret Theatre and 3 minutes by foot from Ashland Library. This inn is 0.2 mi (0.3 km) from Lithia Park and 0.2 mi (0.3 km) from Oregon Shakespeare Festival.. Distances are displayed to the nearest 0.1 mile and kilometer. Oregon Cabaret Theatre - 0.2 km / 0.1 mi Ashland Library - 0.3 km / 0.2 mi Lithia Park - 0.3 km / 0.2 mi Oregon Shakespeare Festival - 0.3 km / 0.2 mi Thomas Theatre - 0.4 km / 0.2 mi Angus Bowmer Theatre - 0.4 km / 0.2 mi Allen Elizabethan Theatre - 0.4 km / 0.2 mi Ashland Creek - 0.5 km / 0.3 mi Southern Oregon University - 1.4 km / 0.8 mi North Mountain Park - 2 km / 1.3 mi Schneider Museum of Art - 2.2 km / 1.4 mi ScienceWorks Hands-On Museum - 2.4 km / 1.5 mi Ashland Dog Park - 2.5 km / 1.5 mi Weisinger Family Winery - 5.4 km / 3.4 mi Grizzly Peak Winery - 5.8 km / 3.6 mi The preferred airport for Winchester Inn is Rogue Valley Intl. Airport (MFR) - 25.3 km / 15.7 mi . In Ashland (Historic Downtown District).
  • You´ll find Winchester Inn in Ashland - 35 S. 2Nd St.,
  • Ashland
  • None - None
  • 0 Adult
  • 1 Room