Ashland, OR

Travel Guide

Ashland
Photo by Lily S
Photo by Lily S
Photo by Jacqueline Sawatzky
Photo by Jacqueline Sawatzky
Photo by Shannon Willitts
Photo by Shannon Willitts
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
Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 out of 5
1193 Siskiyou Blvd, Ashland, OR
The price is ₩104,100 per night from Sep 1 to Sep 2
₩104,100
₩116,071 total
Sep 1 - Sep 2
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! (1,016 reviews)
"It was quiet, nicely appointed, loved the Kuerig coffee appliance."

Reviewed on Aug 19, 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 ₩167,851 per night from Sep 1 to Sep 2
₩167,851
₩201,024 total
Sep 1 - Sep 2
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! (1,464 reviews)
Short stay.
"The property was retro but clean. They probably need to do some updates to the rooms and maybe have designated rooms for dogs. Our room smelled like dog and had a musty odor."

Reviewed on Aug 18, 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 ₩153,152 per night from Sep 7 to Sep 8
₩153,152
₩155,449 total
Sep 7 - Sep 8
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! (1,008 reviews)
"I loved that the working people were very kind to my older Vizsla medical Service dog. I have owned her for 11years—she is now 12. She has been my first & only service dog, and the best! The man who tried to kill me on September 28, 2012 is now dead…so my life in California has returned where I grew ..."

Reviewed on Aug 17, 2025

Comfort Inn & Suites Ashland
See all 743 properties in 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! (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 Jul 28, 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 ...
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 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
See all properties in 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.

Popular places to visit

Ashland is probably best known for the Tony Award-winning Oregon Shakespeare Festival, which I highly recommend checking out if you're in to Shakespeare plays. The statue in the photo is actually a guy in a Shakespearean costume collecting contributions toward a permanent statue of the Bard in Ashland. #WeekendGetaway

Oregon Shakespeare Festival

You can make plans for a show at Oregon Shakespeare Festival during your trip to Ashland. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants.

Oregon Shakespeare Festival
Being the tallest peak in the Siskiyou Mountains, Mt. Ashland offers excellent panoramic views, year round. The ski resort is relatively small, but the runs are steep and a few have cornice drops and chutes. It's a half hour drive from the town of Ashland in good weather. This photo was taken pre-season near the peak after a short yet strenuous ascent. #WeekendGetaway

Mount Ashland Ski Area

Hit the slopes in Ashland with a visit to Mount Ashland Ski Area. Discover the top-notch restaurants and entertainment choices in this walkable area.

Mount Ashland Ski Area

Southern Oregon University

Enjoy the collegiate vibe at Southern Oregon University as part of your travels around Ashland. Experience the area's acclaimed theater scene and lively festivals.

Southern Oregon University

Lithia Park

Explore the great outdoors at Lithia Park, a lovely green space in Ashland. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Lithia Park

Oregon Cabaret Theatre

You can make plans for a show at Oregon Cabaret Theatre during your trip to Ashland. Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants.

Oregon Cabaret Theatre

Howard Prairie Lake

Commune with nature and explore the great outdoors at Howard Prairie Lake during your travels in Ashland. While in this family-friendly area, you can savor the top-notch restaurants.

Howard Prairie Lake