Historic Railroad District Travel Guide

Ashland

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 lively festivals and entertainment choices.

Southern Oregon University

Lithia Park

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

Lithia Park

Allen Elizabethan Theatre

You can enjoy a show at Allen Elizabethan Theatre during your trip to Ashland. Wander around the area's picturesque gardens or experience its entertainment choices.

Allen Elizabethan 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

฿1,141
per traveller
Ashland Puzzling Adventure
Ashland Team Trivia Hunt: New 2024 Mobile Game App!

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

฿1,371
per adult
Ashland Team Trivia Hunt: New 2024 Mobile Game App!
Klamath River- Irongate "Kucascas" Dam Scenic Float

Klamath River- Irongate "Kucascas" Dam Scenic Float

฿6,400
per adult
Klamath River- Irongate "Kucascas" Dam Scenic Float
See all activities in Ashland

Top hotels in Historic Railroad District

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 Wi-Fi, free parking and a fireplace in reception. Popular attractions Ashland Library and Oregon Cabaret Theatre are ...
9.6/10 Exceptional! (76 reviews)
Peerless for the Ashland Shakespeare Festival
"This is a terrific hotel concept. Stayed here three times. And I will again. The rooms are quiet, cosy, and utterly charming. The staff are on call and they answer all questions and take care of any issues quickly. Try this place. I'm a hard core hotel critic and I love the Peerless."

Reviewed on 6 Jul 2025

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The Peerless Hotel by WanderLodges
Hanna's House by WanderLodges
Hanna's House by WanderLodges
4 out of 5
39 4th St, Ashland, OR
The price is ฿4,050 per night from 11 Aug to 12 Aug
฿4,050
฿7,033 total
11 Aug - 12 Aug
includes taxes & fees
Stay at this 4-star business-friendly holiday home in Ashland. Enjoy free Wi-Fi, 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
Rogue Regency Inn and Suites
Rogue Regency Inn and Suites
3 out of 5
2300 Biddle Rd, Medford, OR
The price is ฿3,504 per night from 1 Aug to 2 Aug
฿3,504
฿3,942 total
1 Aug - 2 Aug
includes taxes & fees
Stay at this business-friendly hotel in Medford. Enjoy free breakfast, free Wi-Fi and a free airport shuttle. Our guests praise the breakfast and the pool in ...
8.8/10 Excellent! (2,098 reviews)
Rogue Regency is the best
"Josh at the front desk was fantastic as always, kind and helpful. Jesus gave us a ride to the airport and he is so wonderful and such an awesome member of the staff. Love being able to leave our car at the hotel."

Reviewed on 10 Jul 2025

Rogue Regency Inn and Suites
Quality Inn & Suites Medford Airport
Quality Inn & Suites Medford Airport
2.5 out of 5
1950 Biddle Rd, Medford, OR
The price is ฿3,033 per night from 10 Aug to 11 Aug
฿3,033
฿3,429 total
10 Aug - 11 Aug
includes taxes & fees
Stay at this spa hotel in Medford. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. ...
8.4/10 Very Good! (1,001 reviews)
"Great quality and facility for the price. Liked it"

Reviewed on 8 Jul 2025

Quality Inn & Suites Medford Airport
Ashland Hills Hotel & Suites
Ashland Hills Hotel & Suites
3 out of 5
2525 Ashland St, Ashland, OR
The price is ฿4,230 per night from 3 Aug to 4 Aug
฿4,230
฿5,041 total
3 Aug - 4 Aug
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! (1,440 reviews)
"It’s easy on and off the highway. Definitely recommend for those that want to steer clear of the downtown but still have the amenities of a nice hotel."

Reviewed on 9 Jul 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 ฿3,345 per night from 10 Aug to 11 Aug
฿3,345
฿3,395 total
10 Aug - 11 Aug
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! (1,020 reviews)
"Great."

Reviewed on 11 Jul 2025

Comfort Inn & Suites Ashland
See all 660 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