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9.6 / 10 Guest Rating

Winchester Inn

35 South 2nd Street, Ashland, us

Winchester Inn - main view

About the Property

Luxurious Accommodations
Winchester Inn, located just 300 metres from the Oregon Shakespeare Festival, offers elegantly appointed rooms with 600 thread count sheets, down feather bedding, and private balconies or patios. The rooms are equipped with modern amenities including flat-screen TVs and air conditioning, ensuring a comfortable stay for all guests.

Gourmet Dining Experience
Guests at Winchester Inn can indulge in a 2-course gourmet breakfast included in their stay, prepared with fresh ingredients. The on-site bar and restaurant with an outdoor patio offer a perfect setting to unwind and enjoy delicious meals. Additionally, a coffee bar is available for guests to grab a quick pick-me-up throughout the day.

Concierge Service and Convenience
The hotel provides concierge service to assist guests with any inquiries or bookings, ensuring a seamless and enjoyable stay. With free parking on-site and proximity to Southern Oregon University and Rogue Valley Airport, Winchester Inn offers convenience and accessibility for all travelers.

Book your stay at Winchester Inn now for a luxurious and memorable experience!

Facilities & Amenities

WiFi available
Free WiFi
Parking
Free Parking
Non-smoking rooms
Air conditioning
Restaurant
Heating
Family rooms
Garden

Important Information

Check-in & Out

Check-in
Check-out11:00 AM

Property Notes

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. A deposit may be required at the property.

Check Room Availability

1 night · 2 adults

No rooms available

We couldn't find any available rooms for these dates and guests. Try adjusting your search criteria.

Guest Reviews

9.6
Exceptional619 verified reviews
AI Summary

Guests highly rate the charming location and frequently praise the amazing breakfast.

Categories

Cleanliness8.5
Service10.0
Location10.0
Room Quality9.4
Amenities9.5
Value for Money9.4
Food and Beverage10.0
Overall Experience10.0

Select topics to read reviews

D
DavidusUS
Verified booking
couple
Standard Room
Stayed in Apr 12, 2026

"Excellent"

8.0
Helpful?
J
JackusUS
Verified booking
couple
Standard Room
Stayed in Apr 11, 2026

"Absolute luxury. It was like stepping back into a time where hotels were a true comfortable and luxurious experience"

10.0

Warm, cozy and super inviting!

Literally can’t think of anything.

Helpful?
L
LoidausUS
Verified booking
couple
Standard Room
Stayed in Apr 8, 2026

"Beautiful victorian property!!"

10.0

Location, location! The property is very clean, the staff are very nice. The included breakfast was amazing!

Nothing

Helpful?
C
CatherineusUS
Verified booking
couple
Standard Room
Stayed in Apr 5, 2026

"Would return for another visit"

9.0

Ambience, period attention to detail

Torn sheet, speciality coffee machine broken

Helpful?
Z
Z752MVdanielleb
Verified booking
Family
Standard Room
Stayed in Mar 30, 2026

"Charming!"

10.0

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!

Helpful?
H
H7453IPhenryc
Verified booking
Couples
Standard Room
Stayed in Mar 30, 2026

"Bad rooms and predatory fees"

2.0

TLDR: overpriced, bad rooms and they will rip you off with hidden charges. The morning after checking in here, I summoned to the front desk and very rudely informed I was being charged a $100 per night pet fee. This was not disclosed during booking, even though we specifically informed them we were traveling with a dog. While pet fees are common, $100/night is frankly predatory. My fiance and I found the bed to be uncomfortable and extremely small. The room listed a queen bed. When my fiance asked if was actually a queen, the hotel staff was rude and dismissive. We finally measured the bed with a measuring tape and found that it was a 53" full bed, not a 60" queen - very difficult for two people to sleep in. The hotel staff refused to acknowledge their error, though they did eventually move us to a vacant room with a larger bed for our last night. However, they also charged me another $72.80 for this pleasure without telling me why. At no point did they apologize or offer any other compensation or offer to waive their unreasonable fees. Beyond this, the rooms were dingy and not what I would expect at this price point. Winchester does make a good (though not amazing) breakfast, but it is not worth dealing with low quality rooms, rude staff and predatory hidden fees.

Helpful?
C
CusUS
Verified booking
solo_traveller
Standard Room
Stayed in Mar 30, 2026

"Rooms are poor quality, rude staff and they charge predatory fees."

1.0

Breakfast is pretty good.

Room was dingy, and had a very uncomfortable 53" bed while it was advertised as a queen. Staff was rude when we asked about this and denied the issue. They charge a very $100/night pet fee which was not listed during booking; while pet fees are common, $100 is high to the point of being predatory. They also hit us with an additional $72 fee without saying why.

Helpful?
C
ChrisusUS
Verified booking
solo_traveller
Standard Room
Stayed in Mar 30, 2026

"Exceptional"

10.0
Helpful?
B
BallantiusUS
Verified booking
extended_group
Standard Room
Stayed in Mar 30, 2026

"10/10 - will definitely be staying here again."

10.0

The location was amazing - downtown restaurants, theaters and parks are all walkable. The gardens are beautiful and the free breakfast was delicious. The staff members are all super friendly and helpful as well.

Helpful?
J
jeffjQ3432LW
Verified booking
Family
Standard Room
Stayed in Mar 26, 2026

"Exceptional"

10.0

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

Helpful?