The Winchester Inn, located near the renowned Oregon Shakespeare Festival in Ashland, provides a superb lodging experience for travelers. Rated an impressive 9.4/10 from 387 reviews, the inn offers a variety of room types, including Comfort Triple Rooms, Two-Bedroom Suites, and King and Queen Suites, all equipped with modern amenities.
Guests can enjoy on-site dining at two restaurants and a complimentary gourmet breakfast served daily.
One potential drawback is the inn’s proximity to the Shakespeare Festival, which could be a concern for those seeking a more peaceful retreat. However, the inn’s convenient location, just 984 feet from the festival and 1.6 miles from Southern Oregon University, makes it an ideal base for exploring Ashland’s rich cultural attractions.
The Winchester Inn is well-suited for travelers looking to enjoy the vibrant arts and entertainment scene of Ashland, as well as those seeking a comfortable and well-appointed home base for their stay in the area.
About Your Stay

- The Winchester Inn is a highly-rated 9.4/10 hotel located in Ashland, Oregon, near the renowned Oregon Shakespeare Festival.
- The inn offers a variety of well-appointed room types, including Comfort Triple Rooms, Two-Bedroom Suites, and King and Queen Suites.
- Guests can enjoy on-site dining at two restaurants, Alchemy Restaurant and Bar and Chateaubriand 36, as well as a complimentary gourmet breakfast.
- The inn’s central location provides easy access to Ashland’s cultural attractions, including Southern Oregon University and Lithia Park.
- The Winchester Inn has received consistently positive guest reviews, with high ratings for its staff, facilities, cleanliness, and comfort.
Overview

The Winchester Inn, a charming boutique hotel, is nestled in the heart of Ashland, Oregon, just a stone’s throw from the renowned Oregon Shakespeare Festival.
Located at 35 South 2nd Street, this highly-rated accommodation offers easy access to the city’s cultural attractions.
With an impressive rating of 9.4/10 from 387 reviews, the inn boasts an excellent location, which has been praised by guests.
Situated just 984 feet from the Oregon Shakespeare Festival and within 1.6 miles of Southern Oregon University, the Winchester Inn provides the perfect base for exploring the vibrant city of Ashland.
The hotel’s proximity to the Rogue Valley Airport, just 15 miles away, further enhances its convenience for travelers.
Accommodations

A variety of well-appointed room types cater to the diverse needs of guests at the Winchester Inn.
Accommodations range from cozy Comfort Triple Rooms to spacious Two-Bedroom Suites, as well as Queen Studios and an array of King and Queen Suites.
All rooms feature air conditioning, flat-screen TVs, 600 thread count sheets, and down feather beds, along with private bathrooms stocked with Egyptian cotton towels, bathrobes, and complimentary toiletries.
Some rooms even offer balconies or patios, providing a private outdoor space to enjoy the charming Ashland surroundings.
Whether traveling solo, as a couple, or with family, the Winchester Inn has the perfect room to suit every guest’s needs.
Dining and Amenities

Guests at the Winchester Inn can enjoy a range of dining options and amenities on-site.
The hotel features two on-site restaurants: Alchemy Restaurant and Bar, which offers American, French, and local cuisine, and Chateaubriand 36, a French steakhouse.
Complimentary 2-course gourmet breakfasts are served daily, with options including Full English/Irish, American, and Breakfast to go.
Other amenities include free parking, free Wi-Fi, non-smoking rooms, facilities for disabled guests, family rooms, a bar, and coffee makers in all rooms.
The hotel also adheres to enhanced safety and sanitation protocols to ensure a safe and comfortable stay.
Guest Reviews
According to guest reviews, the Winchester Inn has received exceptional ratings, with an overall score of 9.4 out of 10 from 387 reviews.
Guests have praised the hotel’s staff (9.8), facilities (9.5), cleanliness (9.7), and comfort (9.7).
Common highlights include:
- Excellent gourmet breakfast options
- Comfortable and well-appointed rooms
- Friendly and attentive staff
- Ideal location for exploring Ashland
The Winchester Inn’s high ratings and positive feedback from guests demonstrate its commitment to providing an exceptional hospitality experience.
Policies

The hotel’s check-in and check-out times, along with its cancellation policy and child policy, provide clear guidelines for guests.
Check-in is available from 4:00 PM, and guests must check out by 11:00 AM.
The cancellation policy varies by accommodation type, and a refundable damage deposit of $250 is required at check-in.
Children of all ages are welcome, and extra beds are available for children aged 9 and above at an additional charge.
The hotel also enforces enhanced safety and sanitation protocols in response to COVID-19.
Pets, however, are not allowed on the premises.
Location
The Winchester Inn is conveniently located at 35 South 2nd Street in Ashland, Oregon 97520, just 984 feet from the renowned Oregon Shakespeare Festival and 1.6 miles from Southern Oregon University.
The hotel’s strategic position offers guests easy access to the area’s top attractions:
- Just 15 miles from Rogue Valley Airport, making it a seamless choice for travelers.
- Situated in the heart of Ashland, with a variety of dining, shopping, and entertainment options within walking distance.
- Close proximity to Southern Oregon University, catering to both leisure and business travelers.
- Surrounded by the natural beauty of the Rogue Valley, providing a picturesque setting for a memorable stay.
Facilities

Featuring a range of well-appointed accommodations, the Winchester Inn caters to the diverse preferences of its guests. The hotel offers various room types, including Comfort Triple Rooms, Two-Bedroom Suites, Queen Studios, and an assortment of King and Queen Suites, as well as Family Rooms. All accommodations are outfitted with modern amenities such as air conditioning, flat-screen TVs, 600 thread count sheets, and down feather beds. Private bathrooms are equipped with Egyptian cotton towels, bathrobes, and free toiletries, while some rooms feature balconies or patios. The hotel also provides free parking, free Wi-Fi, and facilities for disabled guests, ensuring a comfortable stay for all.
| Room Type | Amenities |
|---|---|
| Comfort Triple Room | Air conditioning, flat-screen TV, 600 thread count sheets, down feather beds |
| Two-Bedroom Suite | Private bathrooms with Egyptian cotton towels, bathrobes, free toiletries |
| Queen Studio | Some rooms feature balconies or patios |
| King and Queen Suites | Free parking, free Wi-Fi, facilities for disabled guests |
Nearby Attractions

Situated just 984 feet from the renowned Oregon Shakespeare Festival, the Winchester Inn provides an ideal base for visitors to explore the vibrant cultural offerings of Ashland.
Along With the renowned theater, the area boasts several other notable attractions within easy reach:
- Southern Oregon University, just 1.6 miles away, home to the Schneider Museum of Art and a thriving performing arts scene.
- Rogue Valley International-Medford Airport, located 15 miles from the hotel, offering convenient access for travelers.
- The stunning natural beauty of Lithia Park, a short walk from the hotel, featuring Japanese gardens, hiking trails, and a picturesque creek.
- The charming downtown Ashland, brimming with boutiques, galleries, and a bustling culinary scene, all within walking distance of the Winchester Inn.
Booking Your Stay

Tucked away in the heart of Ashland, Oregon, stands the Winchester Inn, a boutique hotel that exudes a refined elegance. As seasoned travelers, we found this hotel to be a true gem, offering a range of upscale amenities that cater to the discerning guest.
The hotel’s convenient location, just steps away from the renowned Oregon Shakespeare Festival and Southern Oregon University, makes it an ideal base for those seeking to enjoy the city’s cultural offerings. With a focus on personalized service and attention to detail, the Winchester Inn provides a rejuvenating experience that sets it apart from the ordinary.
From the exceptional dining options to the inviting ambiance of the guest rooms, every aspect of the Winchester Inn is designed to exceed expectations. Whether you’re planning a romantic getaway or a business trip, this boutique hotel is sure to leave a lasting impression.
To book your stay at the Winchester Inn, simply click the button below, which will take you to our trusted partner, Booking.com. With their competitive prices and user-friendly platform, you can easily secure your reservation and embark on a truly memorable journey.
