The Winchester Inn

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United States
Ashland, OR
The Winchester Inn

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Local Ingredients, Global Cuisine, Craft Cocktails, Boutique Wines, Luxury Accommodations, Affordable Excellence
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A small boutique Inn with award wining restaurant and wine bar that provides innovative cuisine and a selection of wines focusing on Southern Oregon and the Northwest. 2012 has been a busy year for us as we won both Top Chef at the 6th Annual Ashland Culinary Festival as well as Best Chef from Pamela Lanier's B&B guide. Alchemy Restaurant and Bar is located at the Winchester Inn.

11/02/2026

We're back for another year! The Wi******er Inn presents The 39th Annual Dickens Feast! 🎁❄️ Travel back in time to the era of Charles Dickens for a delicious 5 course meal accompanied by live, classic carolers. The night concludes with a visit and personal gift from Santa himself. Join us for one of 9 select nights in December. Tickets are $150 per person, seating begins at 6pm for the 6:15pm event. Call (541) 488-1113 or email [email protected] for tickets.

10/26/2026

Come one, come all to Chateaubriand's Halloween Costume Contest! After the parade, make your way over to our newly built Parisian Terraces for a ghostly good time. Eat, drink & be SCARY!
There are 3 places and 3 prizes to take.
🥉3rd Place: Dinner for 2 at Chateaubriand 36
🥈2nd Place: An overnight stay at The Wi******er Inn
🥇1st: $300 in cold hard CASH!
MUST BE PRESENT AT TIME OF JUDGING TO WIN!
Entertainment provided by Room Service & The Beat Farm. Festivities begin at 5pm. Be there or be scared! 👻

07/08/2026

We're honored to be on the nominee list for USA Today's Reader's Choice #1 B&B once again. 🥂🎉This is our third year in a row to be nominated. In 2024, we had the privilege of winning #1. Last year, we landed at #7. We know that this year, we can make it all the way back to the top. You can vote once a day, every day, for the length of the contest. It takes ten seconds and it makes a real difference. Every single vote counts. https://10best.usatoday.com/awards/winchester-inn-ashland-oregon/ We thank you for all your support and love! ⭐

07/06/2026

You can bring the whole family to enjoy Ashland when you stay in our Duet Suite. 👪Located in its own cottage on property, the two bedroom suite rooms up to 5. Both the king bedroom and queen bedroom have their own ensuite bathrooms with sparkling, tiled walk in showers. This cottage is an ADA Certified Unit. Unique amenities of this room include a microwave, a larger than our standard miniature fridge, kitchenette and hide a bed in the spacious living room. Visit our website winchesterinn.com or call us at 541-488-1113 for bookings and availability!

07/04/2026

Happy 250th Birthday, America! 🎆🇺🇸 We wish everyone a safe and fun Fourth of July.
From our family to yours, Innkeepers & Management of The Wi******er Inn

07/02/2026

Southern Oregon is such a gorgeous and green place to explore. 🌳🌲There are dozens of trails that start all over the valley to get scenic views of Ashland. The Pacific Crest Trail cuts right through the town, giving hikers a bit of respite on their journey. Summer always brings new travelers equipped with huge packs and hiking poles to see the sights. Maybe The PCT isn’t quite your speed. At our Front Desk, we love to recommend ashlandtrails.com. Local Guide Jim has put together an index of all the local hikes by difficulty, accessibility, you name it. There’s even a book copy you can pick up at The Northwest Nature Shop!

06/30/2026

Vive la France! 🇫🇷 Join us at our sister restaurant, Chateaubriand 36, for a Bastille Day Celebration for the ages! Starting from 1pm, enjoy 6 hours of food, fun and music. $40 All Inclusive Food with a cash bar. For more information, call (541) 708-6585.

06/20/2026

Bring your dad out to a dinner that's sure to impress this Father's Day. Our Smashburger has been a local favorite for years. The two crispy edged patties are served on our house made Biroche buns with a drizzle of secret sauce. During Happy Hour at Alchemy, get a b**r, burger and fries all for $20.
Don’t live near home? Send him a gift card so that he can enjoy Alchemy or The Wi******er anytime he’d like.
Gift cards can be purchased online at winchesterinn.com or at our front desk. To view the Alchemy menu, visit alchemyashland.com.

06/18/2026

We have a handful of rooms with cozy window seats offering different views of the property. Our Garden Room is named for its view of our picturesque tiered garden. You can enjoy the sunshine of Ashland both outdoors and indoors right from your room. Book a room with a view today at winchesterinn.com or call us at (541) 488-1113

06/12/2026

Not many people realize that for such a large tourist destination, Ashland is a relatively small town! Some wonder how we can fit so much to see and do in one area. Most of the hustle is located downtown, including curious boutiques, plenty of food offerings and of course, The Oregon Shakespeare Festival⭐. Luckily, our inn is situated in the heart of it all. Only 0.2 miles from the theaters and 0.5 miles from Lithia Park & The Downtown Plaza, you can park your car at the inn when you arrive and not worry about getting back in until it’s time to go home. For more information and recommendations on Ashland, contact us at (541) 488-1113 or via email at [email protected]. You can also visit ashlandchamber.com for listings of businesses and attractions.

Address

35 S 2nd Street
Ashland, OR
97520

Telephone

+15414881113

Website

http://www.winchesterinn.com/

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