Historic Railroad District Travel Guide

Ashland

A rusted metal bridge in a forested area.
A wooden railway bridge with graffiti, surrounded by greenery.
A wooden log cabin with two red-framed windows.
The exterior of Ashland Food Cooperative with a sign reading "Do You Have Your Bags Today?" and a dog and bike free zone sign.


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
The price is ₹14,854 per night from 20 Jul to 21 Jul
₹14,854
₹21,719 total
20 Jul - 21 Jul
includes taxes & fees
Stay at this hotel in Ashland. Enjoy free Wi-Fi, free parking and a fireplace in reception. Popular attractions Oregon Shakespeare Festival and Ashland Library ...
9.6/10 Exceptional! (109 reviews)
"We loved our stay at The Peerless. The room was beautiful and comfortable and the hotel’s lobby, back room, and patio are lovely for hanging out in. The in-room coffee needs filters and a suggestion of amount for those of us who are coffee making impaired. We would stay here again!"

Reviewed on 27 Jun 2026

The Peerless Hotel by WanderLodges
Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
2399 S Pacific Hwy Medford OR
The price is ₹17,757 per night from 1 Jul to 2 Jul
₹17,757
₹21,110 total
1 Jul - 2 Jul
includes taxes & fees
Stay at this golf hotel in Medford. Enjoy free breakfast, free parking and a casino. Our guests praise the breakfast and the pool in their reviews. Popular attractions ...
9.6/10 Exceptional! (1,007 reviews)
"Couldn't recommend this place highly enough. Everything from the check-in to breakfast was perfect."

Reviewed on 27 Jun 2026

Compass by Margaritaville in Medford
Rogue Regency Inn Medford Airport

Rogue Regency Inn Medford Airport

3 out of 5
2300 Biddle Rd Medford OR
The price is ₹10,535 per night from 30 Jun to 1 Jul
₹10,535
₹12,324 total
30 Jun - 1 Jul
includes taxes & fees
Stay at this business-friendly hotel in Medford. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
8.8/10 Excellent! (3,140 reviews)
"The free breakfast is just okay, at least the eggs were warm. There was no TV service, when I called down they pretended not to know anything, but at breakfast next day everyone was complaining about it. Of course they wouldn’t reduce the rate! Not staying there anymore."

Reviewed on 29 Jun 2026

Rogue Regency Inn Medford Airport
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
The price is ₹11,810 per night from 19 Jul to 20 Jul
₹11,810
₹14,112 total
19 Jul - 20 Jul
includes taxes & fees
Stay at this business-friendly hotel in Ashland. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the helpful staff ...
8.8/10 Excellent! (1,500 reviews)
"There was trash on the floor by the curtains when we arrived. There was only one small bar of soap to be used between two sinks and a shower. The ironing board was broken and unusable. No one came to take out the trash or replace the coffee mugs and coffee pods. Not what I expect when paying $300 ..."

Reviewed on 29 Jun 2026

Ashland Hills Hotel & Suites
Prospero's Flagship Inn

Prospero's Flagship Inn

2.5 out of 5
1193 Siskiyou Blvd Ashland OR
The price is ₹8,700 per night from 6 Jul to 7 Jul
₹8,700
₹9,700 total
6 Jul - 7 Jul
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 ...
8.6/10 Excellent! (1,376 reviews)
"Condition of the property was appalling. Filthy carpet in room, worn and torn outdoor carpet in outer hallway. Sheers in room were torn and threadbare. Window in room filthy. Black mold in pool. No answer when phoning front desk repeatedly late at night. Phone line crackly and barely working. Breakfast ..."

Reviewed on 28 Jun 2026

Prospero's Flagship Inn
My Place Hotel-Medford OR

My Place Hotel-Medford OR

3 out of 5
580 Airport Rd Medford OR
The price is ₹8,200 per night from 26 Jul to 27 Jul
₹8,200
₹9,225 total
26 Jul - 27 Jul
includes taxes & fees
Stay at this 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 clean rooms ...
9.2/10 Wonderful! (1,577 reviews)
"When we went to our room after check in there was a gentleman in our room claiming to be head of housekeeping. He had no uniform or name tag like the rest of the employees. When we went down stairs to ask staff at the front desk. He wouldn’t look us in the eyes and he wouldn’t respond except for ..."

Reviewed on 29 Jun 2026

My Place Hotel-Medford OR
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.

Where to stay in Historic Railroad District

Find the best Historic Railroad District areas for the activities you enjoy most.

Historic Downtown District

While visiting Historic Downtown District, you might make a stop by sights like Allen Elizabethan Theatre and Angus Bowmer Theatre.

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.

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 Angus Bowmer Theatre.



Historic Railroad District Travel Guide