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
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St, Ashland, OR
The price is ₩191,177 per night from Aug 17 to Aug 18
₩191,177
₩226,983 total
Aug 17 - Aug 18
includes taxes & fees
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 ...
8.8/10 Excellent! (1,470 reviews)
Stunning, clean, pet friendly
"Amazing mid century modern venue, spotless clean, and pet friendly (at a price per pet). Lovely pool and restaurant, well trained staff at front desk and electric level 1 charging options. There’s a fenced in pet area out back with views of the beautiful hills. Landscaping is beautiful and a short ..."

Reviewed on Jul 20, 2025

Ashland Hills Hotel & Suites
Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

2.5 out of 5
434 S. Valley View Rd., Ashland, OR
The price is ₩142,295 per night from Aug 17 to Aug 18
₩142,295
₩144,429 total
Aug 17 - Aug 18
includes taxes & fees
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 ...
8.6/10 Excellent! (1,011 reviews)
"Great place to stay! Only a short drive into downtown Ashland. Great breakfast."

Reviewed on Jul 19, 2025

Comfort Inn & Suites Ashland
Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 out of 5
1193 Siskiyou Blvd, Ashland, OR
The price is ₩124,384 per night from Aug 10 to Aug 11
₩124,384
₩138,689 total
Aug 10 - Aug 11
includes taxes & fees
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,008 reviews)
"Great stay!"

Reviewed on Jul 19, 2025

Flagship Inn of Ashland
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! (33 reviews)
"Terrific communication with owners, lovely property and close to downtown shops, theatre, etc. Highly recommend!"

Reviewed on May 26, 2025

A Cowslip's Belle Inn
Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges

4 out of 5
1023 E Main St, Ashland, OR
Stay at this 4-star vacation home in Ashland. Enjoy free WiFi, free parking, and a garden. Popular attractions Ashland Library and North Mountain Park are located ...
Beautiful Home Away From Home
"Hannah was such a good communicator and so helpful for my husband and I… We were in Ashland to visit friends and it was such a great place to be. So centrally located but also spacious and clean and beautiful… We would stay there anytime and hope to stay there again"

Reviewed on May 2, 2025

Barclay Klum House by WanderLodges
Hanna's House by WanderLodges

Hanna's House by WanderLodges

4 out of 5
39 4th St, Ashland, OR
Stay at this 4-star business-friendly vacation home in Ashland. Enjoy free WiFi, free parking, and a garden. Popular attractions Ashland Library and Oregon Cabaret ...
"If I were single I could live here. It's that comfortable. The freestanding apartment is ideally located and finished to a very high standard. Amazingly well designed and laid out. Full kitchen, living room, bedroom, and bath. Many, many conveniences. Cafe table in garden outside. We parked once ..."

Reviewed on Sep 19, 2024

Hanna's House by WanderLodges
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.