Winchester Inn | Hotel in Ashland

| 9.4 (427 Reviews) | 24 Bathrooms 59 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. At the hotel each room has a seating area. 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 25 Bedrooms Hotel is suitable for tourists and travelers. It has several amenities that would guarantee your comfort. These amenities include: Security/Safety, Business Services, Sports/Activities, and several others. This is a 5 star rated property and has over 427 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.

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

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

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, 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, 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, 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, USA

May 26, 2026 07:00:00 AM

Reviewer Type: Solo Traveller

Travel Purpose: leisure

Iaroslav, USA

May 4, 2026 07:00:00 AM

Reviewer Type: Couple

Travel Purpose: leisure

Shawna, USA

Apr 28, 2026 07:00:00 AM

Reviewer Type: Couple

Travel Purpose: leisure

Positive: Beautiful inn, rooms with wonderful, thoughtful amenities and lovely garden. Great location if you are coming for the Oregon Shakespeare Festival--can leave your car and just walk to the theater. very close proximity to downtown/shopping district yet feels far away (car and foot traffic). The complimentary breakfast was excellent and nice to have a happy hour even on weekends (with superb bar menu food and reasonably priced drinks). We would definitely plan to stay here again when we come back for the Oregon Shakespeare Festival.

Negative: Not much--everything was great. The only minor complaint is our room was directly below the parlor so could hear people walking due to boards squeaking but this was only an issue before dinnertime and not an issue to interfere with sleep or morning hours.

Summary: Wonderfully relaxing and beautiful place to stay in Ashland

Anne, USA

Apr 25, 2026 07:00:00 AM

Reviewer Type: Solo Traveller

Travel Purpose: leisure

Michele, USA

Apr 23, 2026 07:00:00 AM

Reviewer Type: Solo Traveller

Travel Purpose: leisure

Positive: Clean, quiet, spacious. Good location; great breakfast and delicious in room cookies!!

Negative: That we had to leave!

Summary: Best place to stay in Ashland.

Richard, USA

Apr 22, 2026 07:00:00 AM

Reviewer Type: Couple

Travel Purpose: leisure

Positive: Location was super, hotel was lovely to look at but ur room was near a great deal of outside noise from other guests. The wash basin in the room was not helpful and the bathroom though lovely was tight. Breakfast was a real treat. Dinner at happy hour in the bar was good but service was a bit variable. Too many people for the number of staff. Food was good.

Negative: Room could have been better. An elevator would have been good.

Summary: We would return but want a better room. Location was excellenmt.

Patricia, 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 Parking, Accessibility, Security/Safety, Business Services, Sports/Activities, Restaurant, Entertainment, Air Conditioner, Balcony/Terrace, Child Friendly, Wheelchair Accessible, Fireplace/Heating, Bar, Breakfast, Internet, View, Guest Services, 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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Nightly rates from:

US $417

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Winchester Inn | Hotel in Ashland

Hotel in Historic Downtown District, Ashland

Unique Amenities

Policies

What Our Guests say 500 + Reviews

FAQ's

Is this Winchester Inn pet-friendly for guests?

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

Does the Winchester Inn have a swimming pool?

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

Is Winchester Inn a family-friendly place to stay?

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

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

What cancellation policy is in place for Winchester Inn?

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