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 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 acclaimed theatre scene 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

£26
per traveller
Ashland Puzzling Adventure
Ashland Team Trivia Hunt: New 2024 Mobile Game App!

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

£31
per adult
Ashland Team Trivia Hunt: New 2024 Mobile Game App!
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 ...
9.4/10 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 £90 per night from 13 Aug to 14 Aug
£90
13 Aug - 14 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! (2,230 reviews)
Great experience!
"Inviting staff, quick and easy check in and clean room. Very enjoyable experience!"

Reviewed on 7 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 £115 per night from 10 Aug to 11 Aug
£115
10 Aug - 11 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! (1,463 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 £76 per night from 10 Aug to 11 Aug
£76
10 Aug - 11 Aug
includes taxes & fees
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)
"Good locations d price. Made reservation one day before check I"

Reviewed on 7 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 £90 per night from 10 Aug to 11 Aug
£90
10 Aug - 11 Aug
includes taxes & fees
Stay at this 3-star business-friendly hotel in Central Point. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the ...
7.2/10 Good! (1,010 reviews)
"I understand that is about to be renovated It is showing age"

Reviewed on 7 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 £75 per night from 7 Sept to 8 Sept
£75
7 Sept - 8 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! (1,017 reviews)
"Thank you!"

Reviewed on 6 Aug 2025

Comfort Inn & Suites Ashland
See all 655 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

Default Image

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
Default Image

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
Default Image

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

Choose two or more items and save on your trip: