We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers: Windows: Internet Explorer, Mozilla Firefox. Mac: Safari.
Free Newsletter

Interested in The Winchester Inn and Ashland?

We'll send you updates with the latest deals, reviews and articles for The Winchester Inn and Ashland each week.

  • Save The Winchester Inn
  • E-mail this page

The Winchester Inn


Hotel class 3.0 of 5
35 South Second St., Ashland, OR 97520
Check Rates and Availability
mm/dd/yyyy mm/dd/yyyy
Check Rates
Opens one window for each offer. Please disable pop-up blockers.
Find Cheap Flights to Medford

Reviews you can trust

98% Recommend
5.0 of 5 stars 54 reviews
Excellent
Very good
Average
0
Poor
0
Terrible
By trip type
All (54)
[ Date ] [ Rating ]
Fabulous!
Save Review
5 of 5 stars
octaprev   2 contributions
DECATUR, GA
Nov 10, 2009 | Trip type: Couples New

Large, beautifully appointed room with luxurious, exquisitely comfortable bed Beautifully landscaped grounds - we loved sitting in the gazebo watching birds Located on a quiet, tree-shaded street just a short walk from Ashland's main shopping area Innkeepers are friendly, delightful folks eager to share local knowledge Great experience - we'll be going back soon! more

Save Review
5 of 5 stars
XanaduAl   1 contribution
SF Bay Area
Nov 2, 2009 | Trip type: Solo travel

We stay in a lot of nice places, but Winchester Inn distinguishes itself by having excellent service, wonderful food, very well appointed rooms, and an excellent location. Could not recommend it more. more

nice place
Save Review
5 of 5 stars
markobmf   32 contributions
California
Oct 4, 2009 | Trip type: Couples

The staff was very friendly and accommodating and the room had every amenity you could imagine. Location in relation to the shows was perfect. This is definitely an Inn as opposed to the standard B&B experience which is why I would recommend it. more

Save Review
5 of 5 stars
jrblair   1 contribution
memphis
Oct 4, 2009 | Trip type: Friends getaway

We 3 couples stayed at the Winchester Inn during a one week tour of Oregon. The Inn was most accomodating, the staff were friendly and professional and the food was wonderful. Also appreciated the short walk to Shakespeare theatre more

Management response from
WinchesterInn, Manager

Thank you for the kind words. We hope to see you again next year, and we'll be sure to have everything just so for your next arrival. Best regards, Drew Gibbs

Save Review
5 of 5 stars
lilypodca   1 contribution
san pedro, ca
Oct 3, 2009 | Trip type: Friends getaway

This is a special place in all the right ways. The location is perfect - you can walk to the plays - The staff remembers you but is not intrusive. The breakfast is exceptional as well as being beautifully presented. more

Save Review
5 of 5 stars
CMFtraveler   1 contribution
Washington State
Sep 5, 2009 | Trip type: Couples

We have been staying at the Inn for 15 years. We travel to Ashland once at year to visit OSF and wouldn't think of staying anywhere else. We have stayed in several of the room and do, of course, have our favorites. The Gibbs family and their employees have always been gracious and helpful. The breakfasts are wonderful and included... more

Save Review
5 of 5 stars
pinko33   1 contribution
oregon
Sep 5, 2009 | Trip type: Couples

very pleasant and first rate for breakfast and dinner; one of the best B + B s we have enjoyed, and look forward to enjoy every year more

Save Review
5 of 5 stars
AndrewA26   1 contribution
Portland, Oregon
Sep 1, 2009 | Trip type: Couples

Going to the Shakespeare Festival is what one does in Ashland, Oregon. And to do it while staying at an extremely convenient and charming inn with a great breakfast, fine restaurant, well-stocked wine bar, outdoor seating on nice days and nights and a near perfect staff, makes it THE place from which to do it. more

Management response from
WinchesterInn, Manager

I am thrilled to hear that you enjoyed your stay with us. Hope to see you again next year. Best regards, Drew Gibbs

Save Review
5 of 5 stars
leekCupertino_CA   2 contributions
Cupertino, CA
Aug 26, 2009 | Trip type: Couples

We have stayed in numerous accommodations in Ashland over the past three decades, and the Winchester is the best, hands-down. The location alone would make it a winner - it's a short two-block walk to theatres, plaza, park and most downtown restaurants. Add to that a gorgeous turn-of-the century building, landscaped grounds with fountains and a gazebo and lots of... more

Save Review
5 of 5 stars
brownsugar51   1 contribution
bay area
Aug 21, 2009 | Trip type: Couples

I have always loved England and many aspects of it's history. We were quite pleased to see all of the English touches in our suite. The decor, plush towels, amazing feather bed and pillows. We loved the architecture of the buildings as well as the beautiful gardens. It's the small things that really matter. Kind and friendly people. Fresh ground... more

Check Rates and Availability
mm/dd/yyyy mm/dd/yyyy
Check Rates
Opens one window for each offer. Please disable pop-up blockers.
Write Your Own Hotel Review

Been to The Winchester Inn? Share your experiences!

Write a Review
Add Photos
Add Videos
Travelers Who Viewed This Property Also Viewed
$95*
Check Rates ABS:HotelCheckRates-d95891?src=Hotel_Review&fromServlet=Hotel_Review&Action=QC_AlsoViewed
$154*
Check Rates ABS:HotelCheckRates-d246965?src=Hotel_Review&fromServlet=Hotel_Review&Action=QC_AlsoViewed
Location: Ashland, OR
$140*
*Average price

Do You Own The Winchester Inn?

TripAdvisor has free and easy resources to help you enhance your listing and promote your property.

  • Start Here - Visit Your Owners' Center
  • Add Photo
  • Add Video

The Winchester Inn Address

35 South Second St., Ashland, OR 97520
Ashland B&Bs / Inns The Winchester Inn
5.0/5.0
54