Ashland

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

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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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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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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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
The price is RM379 per night from 20 Aug to 21 Aug
RM379
RM423 total
20 Aug - 21 Aug
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! (1,014 reviews)
"Good sleep"

Reviewed on 17 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 RM509 per night from 1 Sept to 2 Sept
RM509
RM610 total
1 Sept - 2 Sept
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! (1,461 reviews)
"Beautiful grounds surrounding the property. Little dissapointed spa is gone but got over that quickly."

Reviewed on 15 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 RM465 per night from 7 Sept to 8 Sept
RM465
RM472 total
7 Sept - 8 Sept
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 ...
8.4/10 Very Good! (1,005 reviews)
"Pool/Hot tub out of order"

Reviewed on 16 Aug 2025

Comfort Inn & Suites Ashland
See all 744 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 28 Jul 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 2 May 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 19 Sep 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

Oregon Shakespeare Festival

Oregon Shakespeare Festival

You can get tickets for a performance 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
Mount Ashland Ski Area

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

Walk around the campus at Southern Oregon University during your visit to Ashland. Experience the area's acclaimed theatre 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 get tickets for a performance at Oregon Cabaret Theatre during your stay in 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 savour the top-notch restaurants.

Howard Prairie Lake

Things to do

Salem Puzzling Adventure

Ashland Puzzling Adventure

RM150
per traveller
Ashland Puzzling Adventure
See all activities in Ashland