Ashland, OR

Travel Guide

Ashland
Photo by Lily S
Photo by Jacqueline Sawatzky
Photo by Shannon Willitts
Photo by Shannon Willitts

Where to stay in Ashland

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Historic Downtown District

5/5(133 area reviews)

If you're spending some time in Historic Downtown District, Allen Elizabethan Theatre and Oregon Shakespeare Festival are top sights worth seeing.

Historic Downtown District
Road trip food!! I loved the burrito bowl

Historic Railroad District

4.5/5(7 area reviews)

Historic Railroad District might not have many top sights, but Oregon Cabaret Theatre and Allen Elizabethan Theatre are two attractions nearby that you can check out.

Historic Railroad District
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Siskiyou-Hargadine Historic District

4.5/5(12 area reviews)

While visiting Siskiyou-Hargadine Historic District, you might make a stop by sights like Lithia Park and Ashland Library.

Siskiyou-Hargadine Historic District
Walked across the street from the ER and imagine this was the view from a physician parking lot

Skidmore Academy Historic District

5/5(1 area review)

Skidmore Academy Historic District might not have many top sights, but Allen Elizabethan Theatre and Oregon Shakespeare Festival are two attractions nearby that you can check out.

Skidmore Academy Historic District
Comfort Inn & Suites Ashland
Comfort Inn & Suites Ashland
2.5 out of 5
434 S. Valley View Rd., Ashland, OR
The price is AED 369 per night from Jun 2 to Jun 3
AED 369
AED 374 total
includes taxes & fees
2 Jun - 3 Jun
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.4/10 Very Good! (1,000 reviews)
"It hard to find the entrance. And there is indoor pool here."

Reviewed on 19 May 2025

Comfort Inn & Suites Ashland
Ashland Hills Hotel & Suites
Ashland Hills Hotel & Suites
3 out of 5
2525 Ashland St, Ashland, OR
The price is AED 511 per night from May 26 to May 27
AED 511
AED 606 total
includes taxes & fees
26 May - 27 May
Stay at this 3-star ski hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in ...
9/10 Wonderful! (1,433 reviews)
"Very nice rooms. Spacious with hardwood floors. Nice courtyard view. Very comfortable and restful stay."

Reviewed on 17 May 2025

Ashland Hills Hotel & Suites
Stratford Inn
Stratford Inn
2.5 out of 5
555 Siskiyou Blvd, Ashland, OR
The price is AED 349 per night from May 27 to May 28
AED 349
AED 389 total
includes taxes & fees
27 May - 28 May
Book a stay at this business-friendly hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool ...
9.2/10 Wonderful! (1,548 reviews)
"Clean, good location, reasonable price"

Reviewed on 22 May 2025

Stratford Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
A Cowslip's Belle Inn
A Cowslip's Belle Inn
3 out of 5
159 N Main St, Ashland, OR
Stay at this 3-star business-friendly apartment in Ashland. Enjoy free WiFi, free parking, and an in-room coffeemaker. Popular attractions Allen Elizabethan ...
9.6/10 Exceptional! (32 reviews)
"Our room was thoughtfully appointed, clean and comfortable. Cow Slip Bell is a quiet oasis, but conveniently located near the OSF theaters and restaurants. Instructions for parking and checking in were clear and the owner Steve was very helpful. I look forward to staying here again."

Reviewed on 19 May 2025

A Cowslip's Belle Inn
Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.
Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.
Ashland
Stay at this vacation home in Ashland. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Tashi Choling Buddhist Center and Emigrant ...
10/10 Exceptional! (17 reviews)
Do yourself a favor and stay here!!!
"We had the most WONDERFUL experience staying here! The location is beautiful, and the craftsmanship of the home is gorgeous. It was great for our family and we highly enjoyed watching the deer and birds off the deck."

Reviewed on 14 May 2025

Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.
BLOSSOM VIEW COTTAGES  -  Charming Home near OSF Plaza and Downtown
BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown
Ashland
Stay at this vacation home in Ashland. Enjoy a garden, laundry facilities, and patios. Popular attractions Ashland Library and Allen Elizabethan Theatre are ...
Our best stay in Ashland
"The cottage was clean, comfortable, and very well situated in town. The kitchen was well equipped, allowing us to cook most of our meals there. It's in a quiet neighborhood where you can walk to anything you might want."

Reviewed on 21 April 2025

BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Reviews of Ashland

4.6
Top Destination
5 - Excellent
599
5 - Excellent 65%
4 - Good
278
4 - Good 30%
3 - Okay
36
3 - Okay 4%
2 - Disappointing
5
2 - Disappointing 1%
1 - Terrible
1
1 - Terrible 0%

5/5 - Excellent

Verified traveler

I thought Ashland was a quite nice community

5/5 - Excellent

Verified traveler

Lovely town.

5/5 - Excellent

Verified traveler

Ashland is a favorite place to visit for me. Being there during covid shutdown was weird. Will be back when restrictions lifted and performances come back in 2021.

5/5 - Excellent

Verified traveler

Very cute little fosb

4/5 - Good

Verified traveler

My husband and I live in California and we were traveling to Bonney Lake, WA. We are having a home built in Washington. Ashland was the best stop to stay overnight and onto Washington the next day.

5/5 - Excellent

RB

In normal times, Ashland is a charming town and we have been to the Shakespeare festival frequently. Once Covid19 passes, we would definitely like to return.