Winchester Inn | Hotel in Ashland

| 9.4 (409 Reviews) |  24 Bathrooms  59 Guests  Stay&Play
Historic Downtown District Hotel | Winchester Inn

Hotel in Historic Downtown District, Ashland

Historic Charm

Winchester Inn in Ashland offers a historic setting with a beautiful garden, tennis court, and free WiFi. The property features a family-friendly restaurant, bar, and outdoor seating area.

Comfortable Accommodations

Rooms include air-conditioning, private bathrooms, and modern amenities such as mini-bars and flat-screen TVs. Additional facilities include a terrace, balcony, and spa bath.

Dining Experience

Guests enjoy a variety of breakfast options including American, full English/Irish, and continental. The restaurant serves French, American, and local cuisines in a modern and romantic ambiance.

Prime Location

Located 24 mi from Rogue Valley International-Medford Airport, the inn is near Oregon Cabaret Theater (2-minute walk), Oregon Shakespeare Festival (4-minute walk), and Lithia Park (1969 feet). An ice-skating rink is also nearby.

Winchester Inn is located in Ashland.

This 25 Bedrooms Hotel is suitable for tourists and travelers. It has several amenities that would guarantee your comfort. These amenities include: Air Conditioner, Parking, View, and several others. This is a 5 star rated property and has over 409 reviews with the average score of 9.4 . Coming to Ashland and needing a place to stay? Be it for work or for leisure, consider staying at this Hotel for your next visit, you will surely love it.

You can check the reviews and description of this 25 Bedrooms Hotel if you want to learn more about this StayAndPlay.com place in Ashland. These details are authentic, as they are provided by our partner, booking.com.

This Winchester Inn in Ashland is well equipped and has all facilities that have been listed below. Please note that these details were shared to us by booking.com for the listed “Winchester Inn”. We solely rely on their shared details and are regarded as “accurate”. If you have any concerns about the information or accuracy describing this Hotel, please let us know.

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Unique Amenities

  • Air Conditioner
  • Parking
  • View
  • Wheelchair Accessible
  • Balcony/Terrace
  • Accessibility
  • Security/Safety
  • Business Services
  • Sports/Activities
  • Restaurant
  • Bar
  • Guest Services
  • Entertainment
  • Breakfast
  • Child Friendly
  • Heating
  • Internet
  • Laundry
 
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Policies

Check-in
Check-in The minimum age for check-in is 18
Cancellation policy
Cancellation policy Non refundable
Pet Policy
Pet Policy Pets are not allowed
Other Policy
Other Policy 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.
 
35 South 2nd Street, Ashland, OR 97520, USA

What Our Guests say 500 + Reviews

Aug 16, 2026 07:00:00 AM
Reviewer Type: Couple
Travel Purpose: leisure
Positive: Small, quiet and very convenient to the theaters. Helpful and considerate staff. Excellent restaurants.
Negative: Very high bed that could be a challenge to get in and out of.
Summary: Great place to stay if you are attending the Oregon Shakespeare Festival.
Harry Harry, USA
Aug 15, 2026 07:00:00 AM
Reviewer Type: Couple
Travel Purpose: leisure
Positive: From the staff to the facility, this rates as a 5 Star hotel. I plan to make this my go-to hotel for future visits.
Negative: While I gave this the highest possible rating, the bed and sofa bed were very uncomfortable. The main bed was “lumpy” and the sofa bed mattress so thin the metal pieces could be felt.
Summary: A Two-night Stay in a 5-star Hotel
Joel Joel, USA
Aug 14, 2026 07:00:00 AM
Reviewer Type: Solo Traveller
Travel Purpose: leisure
Karen Karen, USA
Aug 14, 2026 07:00:00 AM
Reviewer Type: Couple
Travel Purpose: leisure
Harrison Harrison, USA
Aug 13, 2026 07:00:00 AM
Reviewer Type: Couple
Travel Purpose: leisure
Debra Debra, USA
May 28, 2026 07:00:00 AM
Reviewer Type: Couple
Travel Purpose: leisure
Positive: Wonderful stay - the best bed I ever slept in, in a beautiful room an house, downtown
Negative: Breakfast was too much, and the oatmeal was very dry
Summary: Lovely stay in downturn Ashland
Karin Karin, Belgium
May 28, 2026 07:00:00 AM
Reviewer Type: Solo Traveller
Travel Purpose: leisure
Positive: Exceeded expectations across the board.
Negative: Limited parking
Yano Yano, USA
May 28, 2026 07:00:00 AM
Reviewer Type: Couple
Travel Purpose: leisure
Positive: Beautiful property and gardens. Friendly staff. Delightful breakfast and atmosphere. Super comfortable and quiet rooms. Close walk to Shakespeare festival and fun restaurants and lounges.
Negative: N/A
Summary: Fabulous hotel!
Caroline Caroline, USA
May 26, 2026 07:00:00 AM
Reviewer Type: Solo Traveller
Travel Purpose: leisure
Iaroslav Iaroslav, USA
May 26, 2026 07:00:00 AM
Reviewer Type: Couple
Travel Purpose: leisure
Positive: We had a nice lower floor room which was pleasantly decorated. Staff was friendly and helpful. Location is good... Quiet but close enough to OSF and downtown to walk everywhere. Hearty breakfast included.
Negative: Although comfortable enough, the bed mattress had a soft surface. I prefer a firmer one but it did not detract from our visit.
Summary: Good stay in a well-maintained Victorian mansion
Philip Philip, USA

FAQ's

Is this Winchester Inn pet-friendly for guests? 

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

What time is check-in & check-out at Winchester Inn? 

Check-in time for Winchester Inn starts counting from 4:00 PM and check-out is until 11:00 AM. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

Does the Winchester Inn have a swimming pool? 

No, this Winchester Inn does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Winchester Inn? 

Best-rates for the Winchester Inn starts from $192 per night with includes Air Conditioner, Parking, View, Wheelchair Accessible, Balcony/Terrace, Accessibility, Security/Safety, Business Services, Sports/Activities, Restaurant, Bar, Guest Services, Entertainment, Breakfast, Child Friendly, Heating, Internet, Laundry StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Winchester Inn a family-friendly place to stay? 

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this hotel 5 stars or guests have recommended them suitable for families. As reported by the owner or manager, the hotel has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Winchester Inn wheelchair accessible or offer services for disabled guests? 

Based on the information received from our partner, the Winchester Inn is wheelchair accessible. Likewise, there is an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Winchester Inn? 

Based on the information reported by the owner or manager, the Winchester Inn indicates 1 day stay policy at this hotel. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Winchester Inn? 

Based on the information reported by the owner or manager, details for the cancellation policy for the Winchester Inn are as follows: Non refundable Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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