Winchester Inn

Name: Winchester Inn
Address: 35 South 2nd Street, Ashland, 97520, US

9.3Excellent659 reviewsSee rooms

Hotel

35 South 2nd Street · Ashland

Facilities at a glance

Free Wi-Fi
Parking
Breakfast
Daily housekeeping
Family rooms
Accessible

About this place

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!

Choose your room

Pick check-in and check-out to see live room prices.

43 room types

Choose your room
Room type	Guests	Show prices
Triple Room with Bath 33 m²Twin beds, King bed	Sleeps 3	Show prices
Two-Bedroom Suite 84 m²King bed, Queen bed, Sofa bed	Sleeps 4	Show prices
Suite with Garden View 37 m²Sofa bed, Queen bed	Sleeps 2	Show prices
Queen Suite 37 m²Sofa bed, Queen bed	Sleeps 2	Show prices
Deluxe King Suite 42 m²King bed	Sleeps 2	Show prices
Double Room with Garden View 33 m²Queen bed	Sleeps 2	Show prices
King Room 33 m²King bed	Sleeps 2	Show prices
Standard Queen Room 28 m²Queen bed	Sleeps 2	Show prices
Family Suite 79 m²Queen bed, Sofa bed, King bed	Sleeps 6	Show prices
Comfort Triple Room with Shower 33 m²Twin beds, King bed	Sleeps 3	Show prices
Queen Room 33 m²Queen bed	Sleeps 2	Show prices
Queen Studio 37 m²Sofa bed, Queen bed	Sleeps 2	Show prices
Superior King Suite 84 m²King bed	Sleeps 2	Show prices
King Room 33 m²King bed	Sleeps 2	Show prices
Double Room, 1 Queen Bed (Marjorie Roy) 33 m²Queen bed	Sleeps 2	Show prices
Double Room, 1 King Bed (Enders) 37 m²King bed	Sleeps 2	Show prices
King Suite 42 m²King bed, Sofa bed	Sleeps 2	Show prices
King Room with Balcony 39 m²King bed	Sleeps 2	Show prices
Suite with Mountain View 47 m²King bed, Sofa bed	Sleeps 4	Show prices
King Suite 42 m²King bed	Sleeps 2	Show prices
Deluxe King Suite 46 m²King bed, Sofa bed	Sleeps 2	Show prices
King Room 37 m²King bed, Sofa bed	Sleeps 3	Show prices
Queen Room 33 m²Sofa bed, Queen bed	Sleeps 3	Show prices
Double Room, 1 King Bed (Andrew G) 37 m²King bed	Sleeps 2	Show prices
Suite, 1 Bedroom (Silverdale) 42 m²Queen bed, Single bed	Sleeps 2	Show prices
Double Room, 1 Queen Bed (Patio) 33 m²Queen bed	Sleeps 2	Show prices
Double Room, 1 King Bed (Sunset) 37 m²King bed	Sleeps 2	Show prices
Double Room, 1 King Bed (Peter Benjamin) 37 m²King bed	Sleeps 2	Show prices
Suite, 1 King Bed with Sofa bed (Robert Gordon) 46 m²King bed, Sofa bed	Sleeps 2	Show prices
Suite, 1 Queen Bed with Sofa bed (Brighton) 42 m²Queen bed, Sofa bed	Sleeps 2	Show prices

Choose your room
Room type	Guests	Show prices
Double Room, 1 Bedroom (Sylvan) 33 m²Queen bed, Sofa bed	Sleeps 2	Show prices
Suite, 1 Queen Bed with Sofa bed (Courtyard) 42 m²Queen bed, Sofa bed	Sleeps 2	Show prices
Double Room, 1 Queen Bed (Catharine M) 28 m²Queen bed	Sleeps 2	Show prices
Double Room, 1 King Bed (Eastlake) 33 m²King bed	Sleeps 2	Show prices
Double Room (Queen Anne) 33 m²Queen bed, Twin beds	Sleeps 2	Show prices
Suite, 1 King Bed (Hargadine) 84 m²King bed	Sleeps 2	Show prices
Suite, 2 Bedrooms (Duet Suite) 65 m²King bed, Queen bed, Sofa bed	Sleeps 4	Show prices
Double Room, 1 Bedroom (Garden) 33 m²Queen bed	Sleeps 2	Show prices
Suite, 1 King Bed (Fordyce) 42 m²King bed	Sleeps 2	Show prices
Suite, 1 King Bed (Eleanor Rose) 46 m²King bed	Sleeps 2	Show prices
Suite, 1 King Bed (Barbara Howard) 46 m²King bed	Sleeps 2	Show prices
Family Room 33 m²King bed, Sofa bed	Sleeps 3	Show prices
Deluxe King Studio 42 m²King bed	Sleeps 2	Show prices

What this place offers

Internet

Free Wi-Fi

Parking

Food & drink

Restaurant
Bar
Breakfast

Services

Concierge
Laundry
Daily housekeeping

Family

Family rooms

Accessibility

Accessible

Outdoor

Garden

General

Non-smoking rooms

Activities

Tennis court

Location

Address
35 South 2nd Street, Ashland, 97520, United States
0.4 km from the center of Ashland

Questions about this stay

Quick answers from the information this property gives us.

What are the check-in and check-out times?
Check-in from 16:00. Check-out by 11:00.
Is Wi-Fi included?
Yes, this property lists free Wi-Fi.
Is parking available?
Yes, this property lists parking. Check the room offer for any fee.
Can I add breakfast?
Breakfast is available with selected room offers.

Guest reviews

9.3659 reviews

Reviews from guests who stayed at this hotel, shared by our hotel supplier. Score based on the latest 200 reviews.

Cleanliness8.5

Service10.0

Location10.0

Room quality9.5

Amenities9.5

Value for money9.4

Food and drink10.0

Nora
United States · Couple · November 2026
8.0
“The staff was really friendly. The breakfast that is included was delicious!”
+The room was clean. There were eclairs and fresh flowers on a table when we arrived.
David
United States · Couple · October 2026
10.0
“Perfect”
+Historical with lots of love infused Breakfast was amazing Room was very nice but a little drafty Bar area was epic Chef’ menu to die for… the pastries were the best I ever had
−Our stay was too short
Diane
United States · Couple · October 2026
10.0
+This was a gift for my son and his wife. They commented that their stay was lovely and the staff and facilities were very comfortable and convenient 💕
Ada
United States · Solo · October 2026
10.0
“Decided to stop putting off seeing places. Booked the hotel, a play and were off for a 3 day road trip. Love Ashland w”
+Beautiful Historical home and the garden was lovely. Close to the theater and downtown. We didn’t eat there but it smelled amazing.
Lawrence
United States · Solo · October 2026
10.0
“I came to Ashland to be with friends for their wedding. The hotel was fantastic.”
+Wonderful staff. Great room. Perfect location. A. feal boutique hotel.
−Not much to say about that
Doris
United States · Couple · October 2026
9.0
“A comfortable and gracious old place with a great location and breakfast!”
+The breakfast at the Winchester B&B is always excellant! It is a big part of why we stay there. The staff is friendly and helpful and the food is delicious. We've eaten at the on site restaurant before and also enjoyed that. Our room was comfortable and we slept well in our big bed. Watching the sun come up was lovely! The shower was good; lots of hot water and good water pressure.
−The Winchester B&B is a graceful old place. It has charm but it is worn in places. The carpet on the stairs is dirty, the room smelled musty and the furniture looked worn. We never quite figured out the heater but it wasn't that cold so not a big issue. Despite the quirks we'll probably keep coming back here as we like it overall and it kind of feels like home in Ashland now.
Nuray
United States · Couple · October 2026
9.0
“Charming hotel in a great location.”
+Lovely property, very close to the OSF, maybe a 7 minute walk. Close to restaurants and other shops downtown. The staff was helpful! The room was huge, with a separate sitting area, the bathroom had a large whirlpool tub and a walk in shower! Breakfast was always delicious and our severs were so friendly!
−Some stains on the floors and some of the decorative pillows. But honestly not a huge deal. I would recommend bringing some disposable slippers! The stairs were a little daunting as we were in and out of our room several times a days! But overall very minor issues!
Paul
United States · Couple · September 2026
2.0
−I found the staff to be less than forthwright, and even deceiving in the information they provided. If you choose to stay here becareful of what the staff tells you.
Giuseppa
United States · Solo · September 2026
10.0
+Staff, breakfast
Colleen
United States · Solo · September 2026
10.0
“Wil definitely stay again. Service was impeccable.”
+Gorgeous and well maintained

Good to know

Check-in & check-out
Check-in from 16:00 · check-out until 11:00
Pets
Pets are not allowed

Facilities at a glance

About this place

Choose your room

43 room types

Triple Room with Bath

Two-Bedroom Suite

Suite with Garden View

Queen Suite

Deluxe King Suite

Double Room with Garden View

King Room

Standard Queen Room

Family Suite

Comfort Triple Room with Shower

Queen Room

Queen Studio

Superior King Suite

King Room

Double Room, 1 Queen Bed (Marjorie Roy)

Double Room, 1 King Bed (Enders)

King Suite

King Room with Balcony

Suite with Mountain View

King Suite

Deluxe King Suite

King Room

Queen Room

Double Room, 1 King Bed (Andrew G)

Suite, 1 Bedroom (Silverdale)

Double Room, 1 Queen Bed (Patio)

Double Room, 1 King Bed (Sunset)

Double Room, 1 King Bed (Peter Benjamin)

Suite, 1 King Bed with Sofa bed (Robert Gordon)

Suite, 1 Queen Bed with Sofa bed (Brighton)

Double Room, 1 Bedroom (Sylvan)

Suite, 1 Queen Bed with Sofa bed (Courtyard)

Double Room, 1 Queen Bed (Catharine M)

Double Room, 1 King Bed (Eastlake)

Double Room (Queen Anne)

Suite, 1 King Bed (Hargadine)

Suite, 2 Bedrooms (Duet Suite)

Double Room, 1 Bedroom (Garden)

Suite, 1 King Bed (Fordyce)

Suite, 1 King Bed (Eleanor Rose)

Suite, 1 King Bed (Barbara Howard)

Family Room

Deluxe King Studio

What this place offers

Internet

Parking

Food & drink

Services

Family

Accessibility

Outdoor

General

Activities

Location

Address

Questions about this stay

What are the check-in and check-out times?

Is Wi-Fi included?

Is parking available?

Can I add breakfast?

Guest reviews

Good to know

Check-in & check-out

Pets

Guest reviews