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Winchester Inn

35 South 2nd Street
Rated 9.4 in 391 reviews

Winchester Inn, located in Ashland, United States, provides guests with a charming and comfortable stay highlighted by its unique boutique hotel character. Nestled in the heart of Ashland's vibrant downtown area, the inn is within walking distance of numerous attractions including the renowned Oregon Shakespeare Festival, making it an ideal base for theater enthusiasts and cultural tourists alike.

The Winchester Inn offers a blend of Victorian elegance and modern conveniences, reflected in the carefully appointed guest rooms and suites. Each room is individually decorated, exuding its own personality while offering amenities such as plush bedding and complimentary Wi-Fi, which together enhance the stay for guests seeking both comfort and connectivity.

Guests can enjoy a delightful culinary experience at the on-site restaurant, featuring locally sourced ingredients that showcase the flavors of the region. The award-winning breakfast is particularly noted for its variety and quality, providing a satisfying start to a day of exploration or relaxation in Ashland.

In addition to its prime location and well-appointed accommodations, the Winchester Inn is celebrated for its personal touch and attention to detail, with a staff that is dedicated to offering personalized service. This intimate atmosphere is further enhanced by the lovely gardens that surround the property, offering a serene backdrop for unwinding after a busy day.

The Winchester Inn manages to capture the essence of Ashland's charm and creativity, making it a preferred choice for visitors seeking a memorable and engaging stay in this picturesque Oregon town.

Climate and Weather

January
 8°
 -3°
 7°
 3
Sun hours / day
 19
Rain free days
February
 10°
 -2°
 7°
 4
Sun hours / day
 18
Rain free days
March
 14°
 1°
 7°
 5
Sun hours / day
 18
Rain free days
April
 18°
 5°
 8°
 7
Sun hours / day
 19
Rain free days
May
 23°
 10°
 13°
 9
Sun hours / day
 19
Rain free days
June
 28°
 15°
 18°
 10
Sun hours / day
 19
Rain free days
July
 31°
 18°
 22°
 11
Sun hours / day
 21
Rain free days
August
 30°
 17°
 22°
 10
Sun hours / day
 22
Rain free days
September
 26°
 14°
 20°
 8
Sun hours / day
 21
Rain free days
October
 19°
 8°
 15°
 6
Sun hours / day
 21
Rain free days
November
 12°
 3°
 10°
 4
Sun hours / day
 19
Rain free days
December
 8°
 -1°
 8°
 3
Sun hours / day
 18
Rain free days
Lithia Park
Lithia Park
Park in Ashland, Jackson County, Oregon, United States
260m / 280yd
Ashland Downtown Historic District
Ashland Downtown Historic District
Historic district in Oregon, USA
0m / 0yd
Garfield Park
Park in Jackson County, Oregon, United States of America
1.3km / 0.81mi
Calle Guanajuato
Park in Ashland, Oregon, United States of America
410m / 450yd
Ashland Masonic Lodge Building
Ashland Masonic Lodge Building
United States historic place
400m / 440yd
IOOF Building
IOOF Building
Historic building in Ashland, Oregon, USA
450m / 490yd
Bluebird Park
Park in Jackson County, Oregon, United States of America
480m / 0.3mi
Ashland Springs Hotel
Ashland Springs Hotel
Hotel in Ashland, Oregon, USA
120m / 130yd
First Baptist Church
First Baptist Church
Historic church in Ashland, Oregon, USA
70m / 70yd
Trinity Episcopal Church
Trinity Episcopal Church
Historic church in Ashland, Oregon, USA
140m / 150yd
Liberty Street Park
Park in the United States of America
1.7km / 1.1mi
Railroad Park
Park in Jackson County, Oregon, United States of America
0.7km / 0.43mi
Triangle Park
Park in Jackson County, Oregon, United States of America
0.8km / 0.52mi
Glenwood Park
Park in Jackson County, Oregon, United States of America
1.4km / 0.85mi
North Mountain Park Nature Center
Park in Jackson County, Oregon, United States of America
1.3km / 0.83mi
North Mountain Park
Park in Jackson County, Oregon, United States of America
1.2km / 0.73mi
ScienceWorks
ScienceWorks
Museum in Ashland, Oregon, USA
1.9km / 1.2mi
Scenic Park
Park in Jackson County, Oregon, United States of America
1.7km / 1mi
Hald/Strawberry Park
Park in Jackson County, Oregon, United States of America
1.2km / 0.74mi
Garden Way Park
Park in Jackson County, Oregon, United States of America
2.5km / 1.5mi
Sherwood Park
Park in Jackson County, Oregon, United States of America
2.7km / 1.7mi
Clay Street Park
Park in Jackson County, Oregon, United States of America
2.9km / 1.8mi
Emigrant Lake County Park
Park in Jackson County, Oregon, United States of America
8.5km / 5.3mi
Talent Tiny Park
Miniature city park consisting of a pollinator garden in Talent, Oregon, United States
8.3km / 5.1mi
Hooper Springs County Wayside
Park in Jackson County, Oregon, United States of America
16.1km / 10mi
Jefferson School Park
Park in Jackson County, Oregon, United States of America
17.8km / 11.1mi
South Oakdale Historic District
South Oakdale Historic District
Historic district in Medford, Oregon, USA
18.7km / 11.6mi
Pear Blossom Park
Park in Medford, Oregon, United States
19.8km / 12.3mi
Jacksonville Historic District
Jacksonville Historic District
Historic district in Oregon, USA
24.9km / 15.5mi
Lilly Glen County Campground
Park in Jackson County, Oregon, United States of America
24.8km / 15.4mi
Grizzly County Campground
Park in Jackson County, Oregon, United States of America
24.6km / 15.3mi
Howard Prairie County Resort
Park in Jackson County, Oregon, United States of America
25.1km / 15.6mi
Agate Lake County Park
24.4km / 15.2mi
Howard Prairie County Recreation Area
Park in Jackson County, Oregon, United States of America
25.3km / 15.7mi
Jackson County Sports Park
Park in Jackson County, Oregon, United States of America
25.7km / 16mi
Willow Point County Campground
Park in Jackson County, Oregon, United States of America
25.8km / 16mi
Asperkaha County Campground
Park in Jackson County, Oregon, United States of America
27km / 16.8mi
Sugar Pine County Group Campground
Park in Jackson County, Oregon, United States of America
27.4km / 17.1mi
Medford Oregon Temple
Medford Oregon Temple
Temple of the LDS Church
26.9km / 16.7mi
Klum Landing County Campground
Park in Jackson County, Oregon, United States of America
27.7km / 17.2mi

What to do in Ashland and near Winchester Inn

Lithia Park
Lithia Park
Park in Ashland, Jackson County, Oregon, United States
260m / 280yd
Ashland Downtown Historic District
Ashland Downtown Historic District
Historic district in Oregon, USA
0m / 0yd
Garfield Park
Park in Jackson County, Oregon, United States of America
1.3km / 0.81mi
Calle Guanajuato
Park in Ashland, Oregon, United States of America
410m / 450yd
Ashland Masonic Lodge Building
Ashland Masonic Lodge Building
United States historic place
400m / 440yd
IOOF Building
IOOF Building
Historic building in Ashland, Oregon, USA
450m / 490yd
Bluebird Park
Park in Jackson County, Oregon, United States of America
480m / 0.3mi
Ashland Springs Hotel
Ashland Springs Hotel
Hotel in Ashland, Oregon, USA
120m / 130yd
First Baptist Church
First Baptist Church
Historic church in Ashland, Oregon, USA
70m / 70yd
Trinity Episcopal Church
Trinity Episcopal Church
Historic church in Ashland, Oregon, USA
140m / 150yd
Liberty Street Park
Park in the United States of America
1.7km / 1.1mi
Railroad Park
Park in Jackson County, Oregon, United States of America
0.7km / 0.43mi
Triangle Park
Park in Jackson County, Oregon, United States of America
0.8km / 0.52mi
Glenwood Park
Park in Jackson County, Oregon, United States of America
1.4km / 0.85mi
North Mountain Park Nature Center
Park in Jackson County, Oregon, United States of America
1.3km / 0.83mi
North Mountain Park
Park in Jackson County, Oregon, United States of America
1.2km / 0.73mi
ScienceWorks
ScienceWorks
Museum in Ashland, Oregon, USA
1.9km / 1.2mi
Scenic Park
Park in Jackson County, Oregon, United States of America
1.7km / 1mi
Hald/Strawberry Park
Park in Jackson County, Oregon, United States of America
1.2km / 0.74mi
Garden Way Park
Park in Jackson County, Oregon, United States of America
2.5km / 1.5mi
Sherwood Park
Park in Jackson County, Oregon, United States of America
2.7km / 1.7mi
Clay Street Park
Park in Jackson County, Oregon, United States of America
2.9km / 1.8mi
Emigrant Lake County Park
Park in Jackson County, Oregon, United States of America
8.5km / 5.3mi
Talent Tiny Park
Miniature city park consisting of a pollinator garden in Talent, Oregon, United States
8.3km / 5.1mi
Hooper Springs County Wayside
Park in Jackson County, Oregon, United States of America
16.1km / 10mi
Jefferson School Park
Park in Jackson County, Oregon, United States of America
17.8km / 11.1mi
South Oakdale Historic District
South Oakdale Historic District
Historic district in Medford, Oregon, USA
18.7km / 11.6mi
Pear Blossom Park
Park in Medford, Oregon, United States
19.8km / 12.3mi
Jacksonville Historic District
Jacksonville Historic District
Historic district in Oregon, USA
24.9km / 15.5mi
Lilly Glen County Campground
Park in Jackson County, Oregon, United States of America
24.8km / 15.4mi

About Ashland

Ashland, located in southern Oregon, offers a variety of activities and attractions that cater to different interests. One of the highlights of the city is the Oregon Shakespeare Festival, which presents a range of plays throughout the year, showcasing both classic and contemporary works. The festival has become a cultural cornerstone for the community and attracts theater enthusiasts from all over.

For those who appreciate the outdoors, Lithia Park provides a beautiful setting for leisurely strolls, picnics, and enjoying nature. The park features walking paths, ponds, and well-maintained gardens, making it a serene place to relax. Nearby, the Ashland Creek adds to the park's charm with its soothing sounds and picturesque views.

Art lovers can explore the numerous galleries and studios in the area, which often feature local artists' work. The city's commitment to the arts is evident in its vibrant art scene, with various exhibitions and events throughout the year.

Another interesting aspect of Ashland is its focus on wellness and holistic practices. The town is home to several spas, wellness centers, and health-focused businesses that promote relaxation and rejuvenation.

For those interested in history, the Ashland Historic District offers a glimpse into the city’s past through its preserved buildings and charming architecture. Walking through the district can provide a sense of the local heritage and community spirit.

Lastly, Ashland boasts a number of local wineries and breweries that invite visitors to sample regional wines and craft beers. The surrounding landscape provides an ideal backdrop for wine tasting and enjoying the local beverage culture.

In summary, Ashland's blend of performing arts, natural beauty, wellness options, historical charm, and local culinary experiences makes it a unique destination worth exploring.




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