Historic Railroad District Travel Guide

Ashland

Photo by Inna Blair

Popular places to visit


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! (91 reviews)
Very nice and quiet

Reviewed on 1 Nov 2025

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 ₹8,375 per night from 13 Nov to 14 Nov
₹8,375
per night
13 Nov - 14 Nov
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! (2,574 reviews)
Friendly check in staff

Reviewed on 5 Nov 2025

Rogue Regency Inn and Suites
Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 out of 5
1193 Siskiyou Blvd, Ashland, OR
The price is ₹4,788 per night from 9 Nov to 10 Nov
₹4,788
per night
9 Nov - 10 Nov
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! (1,127 reviews)
Easy check in, convenient location.

Reviewed on 1 Nov 2025

Flagship Inn of Ashland
My Place Hotel-Medford OR

My Place Hotel-Medford OR

3 out of 5
580 Airport Rd, Medford, OR
The price is ₹7,691 per night from 28 Nov to 29 Nov
₹7,691
per night
28 Nov - 29 Nov
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! (1,517 reviews)
The room was perfect. Has a small kitchen with a full size fridge. We have our two dogs only cost 28.13. Comfortable beds nice size TV. Dog area. Large clean bathrooms nice pillows and towels. I like it, we were impressed. Good parking. Everything you need large rooms.

Reviewed on 2 Nov 2025

My Place Hotel-Medford OR
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St, Ashland, OR
The price is ₹8,408 per night from 16 Nov to 17 Nov
₹8,408
per night
16 Nov - 17 Nov
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! (1,495 reviews)
Staff was friendly, property and room was clean. Restaurant staff was great, food was so so.

Reviewed on 2 Nov 2025

Ashland Hills Hotel & Suites
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd, Ashland, OR
The price is ₹7,980 per night from 1 Dec to 2 Dec
₹7,980
per night
1 Dec - 2 Dec
Stay at this hotel in Ashland. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the pool in their reviews. Popular ...
9.2/10 Wonderful! (1,574 reviews)
This was our first time staying here despite coming to Ashland for decades, and we don't feel like we have been missing out on much. The best feature here is the walking distance (in nice weather) to downtown. It was noisy in all ways: thin walls, street traffic, loud guests, etc. We would not stay ...

Reviewed on 3 Nov 2025

Stratford Inn
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