3.5 Star Hotel

Winchester Inn

35 South 2nd Street, Ashland, OR, United States View Map

$152 nightly

includes all fees

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Winchester Inn1/100
Winchester Inn photo 2
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Winchester Inn

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About

Historic Charm Winchester Inn in Ashland offers a historic setting with a beautiful garden, tennis court, and free WiFi. The property features a family-friendly restaurant, bar, and outdoor seating area. Comfortable Accommodations Rooms include air-conditioning, private bathrooms, and modern amenities such as mini-bars and flat-screen TVs. Additional facilities include a concierge service, bicycle parking, and free on-site private parking. Dining Experience Guests can enjoy a variety of breakfast options including American, full English/Irish, and à la carte. The restaurant serves dinner with French, American, and local cuisines, accommodating vegetarian, gluten-free, and dairy-free diets. Prime Location Located 24 mi from Rogue Valley International-Medford Airport, the inn is near Oregon Cabaret Theater (2-minute walk), Ashland Library (984 feet), and Oregon Shakespeare Festival (4-minute walk). An ice-skating rink is also nearby.

468 Reviews

9.3Exceptional
Cleanliness
9.7
Staff
9.8
Location
9.9

What Guests Say

  • “Breakfast is a not your ordinary meal and not to be missed.”
  • “Loved it. Can¿t wait to return.”
Show 50 Verified Reviews

Top Amenities

  • Restaurant
  • Free Internet Access
  • Free Parking
  • Accessible Rooms / Facilities
  • Non-Smoking Rooms
Show All Amenities

Room Options

Our Best Price. GUARANTEED.

Exclusively for Priceline members Details

Suite with Garden View1/1

Suite with Garden View

399 sqft • 1 Queen, 1 Sofabed

  • Air conditioning
  • Alarm clock
  • Bath or Shower
  • Bathrobe(s)
Queen Room1/3

Queen Room

356 sqft • 1 Queen

  • Air conditioning
  • Alarm clock
  • Bath or Shower
  • Bathrobe(s)
Family Suite1/4

Family Suite

851 sqft • 1 King or 1 Queen or 1 Sofabed

  • Additional bathroom
  • Air conditioning
  • Alarm clock
  • Bath or Shower
Deluxe King Studio1/4

Deluxe King Studio

453 sqft • 1 King

  • Air conditioning
  • Alarm clock
  • Bath or Shower
  • Bathrobe(s)
King Room with Balcony1/4

King Room with Balcony

420 sqft • 1 King

  • Air conditioning
  • Alarm clock
  • Balcony
  • Bath or Shower
Suite with Mountain View1/4

Suite with Mountain View

506 sqft • 1 King or 1 Sofabed

  • Air conditioning
  • Alarm clock
  • Bath or Shower
  • Bathrobe(s)

Room Details and Photos

Room Amenities

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    What Guests Loved

    9.3
    Exceptional

    Based on 468 reviews

    Location

    9.9

    Cleanliness

    9.7

    Staff

    9.8

    Overall Quality

    9.5

    Pros +

    • Everything but what was listed below
    • It was perfectly located for our stay which included going to the theater, shopping and hiking.
    • Location can¿t be beat! Easy walk into town. Rooms are beautiful, fantastic breakfast.

    Cons -

    • 6 yr old screaming above us every morning for 1-2hrs. When brought to staffs attention there was no comps or . However they are kid friendly. I totally get that they are kid friendly. But screaming from 6:30am until 7:30
    • The TV cable provider was terrible with a useless guide and poor reception on most stations.
    • Only complaint was the bed was so high a small footstool would have been a welcome addition.
    Business Traveler (17)Solo Traveler (42)Traveling as Couple (199)Family with Young Children (42)Senior Traveler (2)Group Traveler (15)Total (382)
    6ChristopherPosted on: 5-24-2025

    Everything but what was listed below

    6 yr old screaming above us every morning for 1-2hrs. When brought to staffs attention there was no comps or . However they are kid friendly. I totally get that they are kid friendly. But screaming from 6:30am until 7:30

    9PatriciaPosted on: 6-1-2022

    It was perfectly located for our stay which included going to the theater, shopping and hiking.

    The TV cable provider was terrible with a useless guide and poor reception on most stations.

    10Verified Hotel GuestPosted on: 3-1-2022

    Location can¿t be beat! Easy walk into town. Rooms are beautiful, fantastic breakfast.

    Only complaint was the bed was so high a small footstool would have been a welcome addition.

    8KathleenPosted on: 8-22-2021

    Lovely! Free Breakfast was great, special almond muffin for GF folks.

    Difficult for those with some handicap. Stairs, hill, no help with bags. Staffing minimal, they need another person so they can stop multitasking and be available to answer phone, help guests. I suggest asking about stairs or mobility when people reserve.

    10Verified Hotel GuestPosted on: 5-31-2020

    GreT staff, very good restaurant and bar!!

    10RichardPosted on: 1-3-2018

    This hotel was amazing, I will be a loyal guest from here on out.

    10BonitaPosted on: 2-24-2026

    Lovely property and gracious staff. Extra touches such as cookies in the room, ice in ice bucket, phone call to relay room was ready for early check in. Complimentary breakfast was fabulous!

    9KatherinePosted on: 2-19-2026

    Wonderful staff—helpful and cheerful. Bar dinner was fabulous! And most importantly, comfy bed. This is the 3rd or 4th time we’ve stayed here.

    10KarenPosted on: 2-7-2026

    Beautiful vintage hotel with huge rooms, comfortable beds, amenities and Alchemy bar with Happy Hour and restaurant. Fresh baked cookies in room upon arrival as well as fresh flowers.

    10KevinPosted on: 2-5-2026

    Exceptional high-end accommodation in all respects. Their restaurant inside the Victorian home is top rated in Ashland. Excellent complementary breakfast to order,

    NA

    8MartinPosted on: 1-24-2026

    Charming location with well appointed rooms. Huge breakfast.

    Pillows were a bit soft for our liking.

    8NancyPosted on: 1-22-2026

    Great historic inn with period furnishings. Great location to walk downtown. Breakfast is amazing!!!!!

    Carpet needs replacing. No staff around after 5:00 p.m., at least in winter.

    10EleanorPosted on: 1-20-2026

    The room was spacious. We had a room with a king bed and an extra single bed, and a large sitting area. Bathroom was spacious and clean with robes for lounging. The breakfast that was included was fabulous. We have stayed here many times. The bar was great and we also had dinner here one night which was a highlight for us. The staff is also extremely friendly and helpful.

    We don't have any complaints.

    9AlexaPosted on: 1-20-2026

    Winchester is well appointed, great...

    The breakfast was disappointing. My meal arrived cold.

    5annaPosted on: 1-19-2026

    Great location. Friendly staff and good breakfast!

    It’s very old. Creaky floor, full carpet and small room.

    10amadaPosted on: 1-19-2026

    The location was good and the property itself was beautiful. Our bed was very comfortable and our room was oversized and very clean. The breakfast was amazing.

    6WendyPosted on: 1-19-2026

    My husband had a recorded walnut allergy, and the staff delivered cookies with walnuts. Luckily, I noticed before he ate one. This could have been horrible. They did not offer us anything to replace it. Very disappointing and could have had serious consequences! Also, the bathroom door did not shut.

    I got these backwards. See above for dislike. What we enjoyed was the location. The breakfast was deliciius

    10KristyPosted on: 1-17-2026

    I've stayed at the Winchester many times in the past. This trip was much like the others. The room was sparkling clean. The Breakfast was the best breakfast you could get, which is included in the room price. A fabulous choice on the menu. In the room there are great little things waiting for you like, home made cookies, which are amazing; a variety of teas; coffee and a bottle of wine (which you pay for). We couldn't ask for anything more on top of the beautiful grounds and the antique environment, you might expect a horse & carriage to come pick you up.

    I liked everything, I must admit!

    10MatthewPosted on: 1-13-2026

    Location is excellent, right in the middle of town. Able to walk to most things. The breakfast is outstanding.

    We liked everything

    10KyraPosted on: 1-10-2026

    Outstanding breakfast, lovely grounds, loved the fireplace in our room. Off season it’s a great deal and wonderful place to stay. Wouldn’t be able to experience this place in high season.

    Only complaint we had was the plethora of placards in the room. Putting all the instructions, menus etc would have been been much nicer in a nice book. Would be nice if could encourage other guests not to slam their doors. You wouldn’t think you’d need to tell people to be considerate but seems it’s needed.

    Amenities & Policies

    Amenities

    Food & Drinks

    • Restaurant

    Media & Technology

    • Free Internet Access

    Transportation

    • Free Parking
    • Accessible parking

    Health & Safety

    • Health Services
    • Daily disinfection

    Accessibility

    • Handicapped Rooms/Facilities
    • Facilities for disabled guests available

    Kid Friendly

    • Family Friendly

    General

    • No Smoking Rooms/Facilities
    • Themed dinner nights

    Guest policies

    Check-inAfter 4:00 PM
    Check-outBefore 11:00 AM
    InternetFree Wi-Fi is available.
    ParkingFree parking is available.
    Children & Extra BedsChildren of all ages are welcome. Children of age 9 and above can stay with extra bed, subject to additional charges. Children of age 0 to 2 stay free with cot. Children of age 0 to 8 stay free with extra bed.
    PetsPets are not allowed.
    Room RatesAll rates displayed are for two guests unless otherwise noted.

    Important info

    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. Managed by a private host A damage deposit of USD 250.0 is required at checkin. This will be collected by credit card. You should be reimbursed on checkout via credit card, subject to an inspection of the property.

    Location

    Winchester Inn

    35 South 2nd Street, Ashland, OR

    Discover the AreaAshland

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