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 entertainment choices and acclaimed theatre scene.

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

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! (90 reviews)
"A lovely spot to stay! Our room was beautifully furnished and cozy with a historic charm. The outdoor balcony was a great way to wake up with a cup of coffee. Within walking distance of the theaters and downtown."

Reviewed on 8 Oct 2025

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The Peerless Hotel by WanderLodges
Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
2300 Biddle Rd, Medford, OR
Fully refundableReserve now, pay when you stay
The price is ₹9,579 per night from 15 Oct to 16 Oct
₹9,579
₹10,776 total
15 Oct - 16 Oct
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! (2,486 reviews)
"Just love this motel and staff ... definitely my number one"

Reviewed on 7 Oct 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 ₹9,954 per night from 20 Oct to 21 Oct
₹9,954
₹11,985 total
20 Oct - 21 Oct
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! (1,467 reviews)
"Very friendly staff."

Reviewed on 6 Oct 2025

Ashland Hills Hotel & Suites
My Place Hotel-Medford OR

My Place Hotel-Medford OR

3 out of 5
580 Airport Rd, Medford, OR
The price is ₹7,047 per night from 3 Nov to 4 Nov
₹7,047
₹7,928 total
3 Nov - 4 Nov
includes taxes & fees
Stay at this 3-star business-friendly hotel in Medford. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the ...
9/10 Wonderful! (1,481 reviews)
"The staff were great, location to airport was perfect, room was clean and welcoming, and their taxi service to the airport was the icing on the cake!!"

Reviewed on 7 Oct 2025

My Place Hotel-Medford OR
Quality Inn & Suites Medford Airport

Quality Inn & Suites Medford Airport

2.5 out of 5
1950 Biddle Rd, Medford, OR
The price is ₹6,936 per night from 11 Nov to 12 Nov
₹6,936
₹7,842 total
11 Nov - 12 Nov
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! (1,013 reviews)
Nice place and convenient to the airport
"Shuttle was very accommodating and easy to find."

Reviewed on 10 Oct 2025

Quality Inn & Suites Medford Airport
Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 out of 5
1193 Siskiyou Blvd, Ashland, OR
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 ...
8.6/10 Excellent! (1,079 reviews)
"great room, amazing staff! would stay here again!"

Reviewed on 9 Oct 2025

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Flagship Inn of Ashland
See all 666 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