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! (94 reviews)
Very charming hotel, the common areas were cute and clean with free coffee and tea. My husband and I stayed in the anniversary sweet for two nights. We had an excellent stay! Checked in right at 4:00pm and self check in was a breeze. Our room was super spacious and very clean. The bathtubs were my ...

Reviewed on 7 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
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! (2,599 reviews)
Wonderful food in the pub Beds were great

Reviewed on 11 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
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! (1,151 reviews)
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Reviewed on 15 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 ₹7,698 per night from 29 Nov to 30 Nov
₹7,698
₹8,661 total
29 Nov - 30 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! (1,494 reviews)
Room was nice.

Reviewed on 15 Nov 2025

My Place Hotel-Medford OR
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
The price is ₹8,408 per night from 15 Dec to 16 Dec
₹8,408
₹10,261 total
15 Dec - 16 Dec
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! (1,495 reviews)
Great room location to courtyard to take family pup out side. Quiet. Comfy bed

Reviewed on 10 Nov 2025

Ashland Hills Hotel & Suites
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd, Ashland, OR
Fully refundable
The price is ₹7,980 per night from 15 Dec to 16 Dec
₹7,980
₹8,898 total
15 Dec - 16 Dec
includes taxes & fees
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! (1,577 reviews)
We loved our stay. The room was huge! 2 queen beds, kitchenette, nook. The mattress was perfect and my wife had her best sleep in years. All of the staff were helpful with the woman taking care of the breakfast room a true highlight. We highly recommend this hotel. It is older, but managed with exceptional ...

Reviewed on 13 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