Built in 1886 and renovated in 1983, the Winchester Inn is a historic boutique hotel located in downtown Ashland, Oregon. It provides a luxury lodging experience that blends Victorian charm with modern amenities, suitable for romantic getaways or vacations. The inn's prime location makes it ideal for experiencing Ashland's vibrant arts and culture scene, with key attractions just a short walk away.
Should you book Winchester Inn?
A luxury lodging experience in a historic building with modern amenities, close to Ashland's main attractions.
Best for
- Couples seeking a romantic getaway
- Arts and culture enthusiasts
- Walkable access to downtown
- Luxury historic stay
Maybe not ideal for
- Those seeking a resort experience
- Budget travellers
Historic Victorian Charm
Originally constructed in 1886, this family-run hotel offers a luxury lodging experience. Rooms and suites feature elegant decor, 600 thread count sateen sheets, and fine toiletries.
Downtown Ashland Location
Conveniently located within walking distance of the Oregon Shakespeare Festival and the Oregon Cabaret Theater. Explore local shops and restaurants easily from this central spot.
On-site Dining
Alchemy Restaurant and Bar offers fine dining with craft cocktails and locally-sourced seasonal ingredients. Chateaubriand 36 is a French-inspired steakhouse.
Comfortable Accommodations
Guest rooms and suites are equipped with private bathrooms, flat-screen TVs, mini-bars, and air-conditioning. Suites offer extra space and luxury amenities.
Rooms & rates
What you'll enjoy
Gallery
Amenities & facilities
Most popular facilities
- Non-smoking rooms
- Free Wifi
- Free parking
- Facilities for disabled guests
- 2 restaurants
- Family rooms
- Tea/Coffee Maker in All Rooms
- Bar
Great for your stay
- 2 restaurants
- Parking
- Private bathroom
- Air conditioning
- View
- Free Wifi
- Free parking
- Non-smoking rooms
Private bathroom
- Toilet paper
- Towels
- Bath or shower
- Toilet
- Free toiletries
- Bathrobe
- Hairdryer
- Shower
Bedroom
- Linens
- Wardrobe or closet
- Alarm clock
- Extra long beds (> 80 inches)
View
- View
Outdoors
- Outdoor furniture
- Garden
Location
35 South 2nd Street, Ashland, OR 97520, United States, Ashland, Oregon
Winchester Inn is located in Ashland, Oregon.
5 sights nearby, all within 0.5 mi; the closest is Trinity Episcopal Church at 500 ft.
Things to do nearby
- Trinity Episcopal Churchplace of worship500 ft
- Calle Guanajuatopark0.3 mi
- Bluebird Parkpark0.3 mi
- Japanese Gardengarden0.4 mi
- Lithia Parkhistoric site0.5 mi
Straight-line distances from the property · data © OpenStreetMap contributors
What guests say
9.4 / 10 · Wonderful on Booking.com, from 409 guest reviews
Winchester Inn earns strong praise across nearly all reviews for its attentive, professional staff, excellent breakfast, and prime location near Ashland's theatres, with charming historic rooms and thoughtful touches adding to the appeal. However, recurring concerns include bed comfort issues, unexpected surcharges at breakfast, and the absence of an elevator that limits accessibility. The on-site dinner experience received at least one notably poor report, suggesting the restaurant is inconsistent.
Reviews scoring 9–10: 28 · average 9.8
They wrote about: breakfast, room, staff
Reviews scoring 7–9: 2 · average 8
They wrote about: location, staff, room
No reviews in the selected score range.
Good to know
House rules
- Check-in
From 4:00 PM
Guests are required to show a photo ID and credit card at check-in.
You need to let the property know what time you'll be arriving in advance.
- Check-out
Until 11:00 AM
- Cancellation/ prepayment
Cancellation and prepayment policies vary according to accommodation type. Enter your stay dates and check the conditions of your selected option.
- Refundable damage deposit
A damage deposit of US$250 is required on arrival. This will be collected by credit card. You should be reimbursed on check-out. Your deposit will be refunded in full by credit card, subject to an inspection of the property.
- Pets
Pets are not allowed.
Frequently asked questions
What is the location of Winchester Inn?
The hotel is situated in downtown Ashland, Oregon, within walking distance of local theaters and the library. It is also a short distance from parks and historic sites.
Are there restaurants on-site?
Yes, the Winchester Inn has two restaurants: Alchemy Restaurant and Bar, a fine dining establishment, and Chateaubriand 36, a French-inspired steakhouse.
What parking is available?
The inn offers private parking for guests, which is complimentary.
What are the room amenities?
Rooms are equipped with air-conditioning, private bathrooms, mini-bars, flat-screen TVs, tea/coffee making facilities, and a refrigerator. Some rooms have garden views.
Does the inn offer breakfast?
Yes, the property offers exceptional breakfast, with gourmet breakfast included for guests staying in the suites.
Is Wi-Fi available?
Yes, complimentary high-speed wireless internet access is available for guests.
Are family rooms available?
Yes, the hotel offers family rooms, and specific suites are suitable for families with sofa beds.
Can I golf nearby?
Yes, a golf course is available within 2 miles (approximately 3.2 km) of the hotel, available at an additional charge.
Is there a spa on-site?
The hotel does not feature an on-site spa.