Ashland Travel Guide

Tourist 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

While visiting Historic Downtown District, you might make a stop by sights like Allen Elizabethan Theatre and Oregon Shakespeare Festival.

Historic Downtown District
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Historic Railroad District

While Historic Railroad District isn't home to many top sights, Oregon Cabaret Theatre and Allen Elizabethan Theatre are some notable places to visit nearby.

Historic Railroad District
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Siskiyou-Hargadine Historic District

If you're spending some time in Siskiyou-Hargadine Historic District, Lithia Park and Ashland Library are top sights worth seeing.

Siskiyou-Hargadine Historic District
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Skidmore Academy Historic District

While Skidmore Academy Historic District may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Allen Elizabethan Theatre and Oregon Shakespeare Festival.

Skidmore Academy Historic District
Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 out of 5
1193 Siskiyou Blvd, Ashland, OR
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 staff ...
8.8/10 Excellent! (1,002 reviews)
"Rooms are nice size and very clean. It's very quiet and fairly close to town. Beds are good, pillows also good. Staff was very friendly and helpful. We'd stay here again. The price was right."

Reviewed on 22 Aug 2025

Flagship Inn of Ashland
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St, Ashland, OR
The price is Rp1.969.708 per night from 3 Sept to 4 Sept
Rp1.969.708
Rp2.358.991 total
3 Sept - 4 Sept
includes taxes & fees
Stay at this 3-star ski hotel in Ashland. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in ...
8.8/10 Excellent! (1,450 reviews)
"Absolutely beautiful view"

Reviewed on 20 Aug 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 Rp1.712.277 per night from 21 Sept to 22 Sept
Rp1.712.277
Rp1.737.961 total
21 Sept - 22 Sept
includes taxes & fees
Stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
8.6/10 Excellent! (1,000 reviews)
"Great!"

Reviewed on 20 Aug 2025

Comfort Inn & Suites 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 Wi-Fi, free parking and an in-room coffee maker. Popular attractions Allen Elizabethan ...
9.6/10 Exceptional! (35 reviews)
"What a wonderful place to stay! The owners were very cordial and offered suggestion about places to go. We particularly loved to Koi pond right off our deck."

Reviewed on 28 Jul 2025

A Cowslip's Belle Inn
Grandview of Ashland

Grandview of Ashland

3 out of 5
821 Grandview Dr, Ashland, OR
Stay at this 3-star holiday home in Ashland. Enjoy free Wi-Fi, free parking and a sauna. Popular attractions Oregon Shakespeare Festival and Thomas Theatre are ...
10/10 Exceptional! (1 review)
"I absolutely fell in love with this property it was so beautiful from the moment we drove up the hill to see this gorgeous house at the top. The yard and garden was a surprise. I wasn’t expecting to have such a peaceful place to stay the pictures don’t even do it justice. I would definitely Want ..."

Reviewed on 15 Apr 2025

Grandview of Ashland
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 holiday home in Ashland. Enjoy free Wi-Fi, free parking and a garden. Popular attractions Ashland Library and North Mountain Park are located ...
10/10 Exceptional! (5 reviews)
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 2 May 2025

Barclay Klum 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

Things to do

Cities near Ashland