Winchester Inn

35 S. 2nd St., Ashland, OR 97520 US near Exit 14 on I-5 (~2.4mi)

View Map Reservations: +1-800-219-2797

3.5 Star Property In Ashland (Historic Downtown District)

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Excellent

5.0/5

Based on 276 guest reviews

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Free breakfast
Free WiFi
Smoke-free property
Free newspapers in lobby
Free self parking
Free cooked-to-order breakfast

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03/18/2026 - 03/19/2026

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7 bookings in the last 48 hours

Standard prices by room type for the next 60 days

Rates shown are nightly rates before taxes and do not necessarily reflect all discounts available. The chart provides the cheapest public rates available by room type.

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Winchester Inn

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Property Description

The Winchester Inn offers affordable excellence with an attention to detail and comfort; while the restaurant and wine bar offer innovative cuisine, award wining wine lists, and attentive service in a warm cozy atmosphere.This traditional Victorian stately home is in perfect harmony with its surroundings, situated in the midst of an English country garden. As guests approach the main building pansies line the path that leads to the front entrance, the gardens are encompassed by a herbaceous border whilst colorful tulips are scattered throughout the grounds. The interior is no less stunning, the rooms are a tribute to comfort and subtlety, with soft, warm shades and opulent furniture. Dinner may be taken in the popular restaurant, whilst in the summer, food is served outdoors. Wherever guests dine, the sumptuous flavors and textures are of the highest standards. The new wine bar provides a nice tasting of local wineries and a special nightly wine flight. The quaint gazebo is a perfect site for small weddings and receptions. Sporting activities available nearby include fishing, golf, ballooning or skiing while the more artistic guest may wish to visit the Ashland Shakespeare Festival or the Britt Music Festival, information on which may be obtained from the inn.