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Surrounded by breathtaking scenery, majestic mountains, rushing rivers, rolling foothills and dramatic landscapes, Ashland is a gorgeous little city with an arts scene as vibrant as its setting. Ashland hosts festivals for all seasons, with Christmas celebrations and the Oregon Shakespeare Festival in winter, a film festival in the spring, classical music festival in summer and wine tasting celebrations in the autumn.
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Most Popular Hotels
as Ranked by TripAdvisor™ Travelers
3-Star Hotels - Save up to 44%
The Winchester Inn
The Winchester Inn
Traveler Rating:5.0 of 5 stars
Latest review: "Beautiful Victorian Inn exceeds expectations in every category"
I've been staying at the Winchester Inn for my annual trip to the Oregon Shakespeare Festival for about 10 years. (And for about 8 years before that I...
Check Rates    Average price*: $293
Country Willows Bed and Breakfast Inn
Country Willows Bed and Breakfast Inn
Traveler Rating:4.5 of 5 stars
Latest review: "Surprising Find in Ashland"
We came to Ashland for the Shakespeare and some whitewater rafting and hoped the place to stay would be adequate, but Country Willows would be a fantastic...
Check Rates    Average price*: $172
The Village Suites at Ashland Hills
The Village Suites at Ashland Hills
Traveler Rating:4.5 of 5 stars
Latest review: "Good Value"
I chose this hotel based on Tripadvisor reviews and was not dissapointed! Staff was friendly and welcoming and very helpful. Our room was spacious, very...
Check Rates    Average price*: $116
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Arden Forest Inn
Traveler Rating:5.0 of 5 stars
Latest review: "The Arden Forest Inn is a great place to enhance your OSF experience"
We have been OSF members for 20 years and for a decade we have thoroughly enjoyed our annual stay at the Arden Forest Inn. The rooms are impeccably clean...
Average price*: $140
Ashland Mountain House
Traveler Rating:4.5 of 5 stars
Latest review: "Ashland Mountain's Brick House..."
is an absolute delight! and one of the selections you can decide on as your room of choice.Innkeeper John is immediately at the ready to greet you and...
Average price*: $150
Iris Inn
Iris Inn
Traveler Rating:4.5 of 5 stars
Latest review: "Iris Inn is one of our favorite bed and breakfasts"
The Iris Inn, run by Vicki and Greg, is one of our favorite b&bs, and we've stayed at many. Introduced to it by friends, we've stayed there for four...
Check Rates    Average price*: $180
A Cowslip's Belle-Bed & Breakfast
Traveler Rating:4.5 of 5 stars
Latest review: "Above Average All the Time..."
Ashland is a special place and Cowslip's Belle B&B makes our twice-yearly trips like coming home. Long-time owners Jon & Carmen are wonderful hosts & great...
Check Rates    Average price*: $236
A Midsummer's Dream Bed and Breakfast
Traveler Rating:4.0 of 5 stars
Latest review: "Great Place in Ashland"
A Midsummer's Dream B and B is just perfect for a weekend in Ashland. The owner, Lisa, is friendly and very helpful. We were greeted by homemade cookies...
Average price*: $180
Plaza Inn & Suites at Ashland Creek
Plaza Inn & Suites at Ashland Creek
Traveler Rating:4.0 of 5 stars
Latest review: "Great location and room for a great price"
We stayed for the first time at the Plaza Inn and Suites last week for our 10 year wedding anniversary. We are on a VERY limited budget and were able to...
Check Rates    Average price*: $189
Romeo Inn
Traveler Rating:4.5 of 5 stars
Latest review: "Home Away from Home"
It's spring, a reminder that summer trips are just around the corner. I am looking forward to our annual stay at the Romeo Inn. It's like being at home...
Average price*: $122
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