Winchester Inn | Hotel in Ashland

| 9.5 (396 Reviews) |  22 Bathrooms  49 Guests  Stay&Play
Historic Downtown District Hotel | Winchester Inn

Hotel in Historic Downtown District, Ashland

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, 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 Lithia Park. Rogue Valley International-Medford Airport is 24 miles from the property.

Winchester Inn is located in Ashland.

This 22 Bedrooms Hotel is suitable for tourists and travelers. It has several amenities that would guarantee your comfort. These amenities include: Business Services, Restaurant, Bar, and several others. This is a 5 star rated property and has over 396 reviews with the average score of 9.5 . 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 22 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
  • Fireplace/Heating
  • Restaurant
  • Bar
  • Guest Services
  • Entertainment
  • Breakfast
  • Child Friendly
  • Internet
  • Laundry
 
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Policies

Check-in The minimum age for check-in is 18
Cancellation policy Non refundable
Pet Policy Pets are not allowed
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 29, 2025 07:00:00 AM
Reviewer Type: Couple
Travel Purpose: leisure
Nancy Nancy, USA
Aug 27, 2025 07:00:00 AM
Reviewer Type: Solo Traveller
Travel Purpose: leisure
Positive: The staff was very friendly and professional! The food was spectacular.
June June, USA
Aug 23, 2025 07:00:00 AM
Reviewer Type: Couple
Travel Purpose: leisure
Aug 17, 2025 07:00:00 AM
Reviewer Type: Couple
Travel Purpose: leisure
Mark Mark, USA
Aug 16, 2025 07:00:00 AM
Reviewer Type: Couple
Travel Purpose: leisure
Positive: The breakfast was absolutely fantastic! The bathroom with all the products, the lush sheets and balcony, in room coffee - all were wonderful. Thank you!
Leslie Leslie, USA
Aug 15, 2025 07:00:00 AM
Reviewer Type: Couple
Travel Purpose: leisure
Positive: The staff see to every detail. We felt as though we were living in luxury! Location was perfect and the grounds are beautiful.
Negative: Can’t think of a thing!
Summary: We absolutely loved our stay! We will definetly return on our next trip to Ashland.
Kris Kris, USA
Apr 19, 2025 07:00:00 AM
Reviewer Type: Couple
Travel Purpose: leisure
Positive: Fantastic vintage hotel with spacious room, nice balcony and a fabulous restaurant (Alchemy) just downstairs. Will definitely stay again!
Stephen Stephen, USA
Mar 30, 2025 07:00:00 AM
Reviewer Type: Couple
Travel Purpose: leisure
Eugene Eugene, Ukraine
Mar 28, 2025 07:00:00 AM
Reviewer Type: Couple
Travel Purpose: leisure
Positive: great location, clean, classy, great breakfast
Negative: nada
Summary: great location, clean, classy, great breakfast
scott scott, USA
Mar 25, 2025 07:00:00 AM
Reviewer Type: Couple
Travel Purpose: leisure
Positive: Garden breakfast
Negative: Heavy luggage up staircase
Addicott Addicott, 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 $417 per night with includes Air Conditioner, Security/Safety, Entertainment, Internet, View, Balcony/Terrace, Business Services, Restaurant, Bar, Breakfast, Accessibility, Fireplace/Heating, Child Friendly, Guest Services, Parking, Wheelchair Accessible, Sports/Activities, 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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US $417
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