Historic Railroad District Travel Guide

Tourist Guide

Photo by Inna Blair
Photo by Inna Blair

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

Activities

Salem Puzzling Adventure

Ashland Puzzling Adventure

AU$53
per traveller
Ashland Puzzling Adventure
See all activities in Ashland

Our pick of the best Historic Railroad District Hotel Deals

The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges

2 out of 5
243 4th St, Ashland, OR
Stay at this hotel in Ashland. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Ashland Library and Oregon Cabaret Theatre are ...
9.4/10 Exceptional! (81 reviews)
Unique 21st anniversary stay!
"It was very clean and romantic as advertised. Loved the quiet space and tubs. Unique and luxurious hotel experience."

Reviewed on 30 Jul. 2025

Get rates
The Peerless Hotel by WanderLodges
Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
2300 Biddle Rd, Medford, OR
The price is AU$186 per night from 12 Aug to 13 Aug
AU$186
12 Aug - 13 Aug
includes taxes & fees
Book a stay at this business-friendly hotel in Medford. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
8.8/10 Excellent! (2,241 reviews)
"Rooms clean, everything was do convenient, restaurant and the airport was just down the road, quick and easy to get to."

Reviewed on 10 Aug. 2025

Rogue Regency Inn and Suites
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St, Ashland, OR
The price is AU$231 per night from 11 Aug to 12 Aug
AU$231
11 Aug - 12 Aug
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! (1,463 reviews)
"This was a clean, well maintained hotel with a friendly helpful staff. The breakfasts were delicious! It was in a great location so that we could visit the Oregon Shakespeare festival and other downtown restaurants. The pool and hot tub were wonderful!"

Reviewed on 5 Aug. 2025

Ashland Hills Hotel & Suites
Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 out of 5
1193 Siskiyou Blvd, Ashland, OR
The price is AU$143 per night from 11 Aug to 12 Aug
AU$143
11 Aug - 12 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! (1,008 reviews)
"Bed comfort was great! Great rest after a long day of driving!"

Reviewed on 9 Aug. 2025

Flagship Inn of Ashland
La Quinta Inn & Suites by Wyndham Central Point - Medford

La Quinta Inn & Suites by Wyndham Central Point - Medford

3 out of 5
1777 La Rue Dr, Central Point, OR
The price is AU$185 per night from 17 Aug to 18 Aug
AU$185
17 Aug - 18 Aug
includes taxes & fees
Stay at this 3-star business-friendly hotel in Central Point. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
7.2/10 Good! (1,006 reviews)
"I enjoyed my room, it was very quiet and clean. It was a pleasant surprise, since the exterior landscaping is neglected."

Reviewed on 10 Aug. 2025

La Quinta Inn & Suites by Wyndham Central Point - Medford
Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

2.5 out of 5
434 S. Valley View Rd., Ashland, OR
The price is AU$169 per night from 2 Sept to 3 Sept
AU$169
2 Sept - 3 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 ...
8.6/10 Excellent! (1,004 reviews)
"Swimming pool and hot tub were not available due to repairs. We were not aware of this problem until we arrived"

Reviewed on 9 Aug. 2025

Comfort Inn & Suites Ashland
See all 657 properties in Historic Railroad District
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.

Other neighbourhoods around Historic Railroad District

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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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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

Historic Railroad District Travel Guide

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