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 8 Jul to 9 Jul
₹17,757
₹21,110 total
8 Jul - 9 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! (1,009 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 ₹9,785 per night from 5 Jul to 6 Jul
₹9,785
₹11,481 total
5 Jul - 6 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! (3,143 reviews)
"From the time you walk in the carpet is so dated and stained the room we got the bed was broken the room just did not feel comfortable please find another place to stay"

Reviewed on 30 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 ₹12,678 per night from 12 Jul to 13 Jul
₹12,678
₹15,081 total
12 Jul - 13 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! (1,502 reviews)
"Lots of pillows and a comfy bed. Really enjoyed our stay. Room was a lot bigger than expected"

Reviewed on 30 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 ₹8,805 per night from 6 Jul to 7 Jul
₹8,805
₹9,818 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! (1,377 reviews)
"We entered the room and the carpet looked like a crime scene. Big stains of unknown origin. Here's a screengrab of the video. There were picture holders on the walls with no pictures. The towels had threads hanging from them. Tried to switch rooms but nothing on the ground floor available, was dealing ..."

Reviewed on 29 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 ₹8,212 per night from 26 Jul to 27 Jul
₹8,212
₹9,239 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! (1,580 reviews)
"Well, if you are frequent traveler and plan on spending substantial money on their establishment, like I did with choice at 160 nights a year for 11 years I would highly recommend that you go to choice. I would even recommend Motel 6 and Travel Lodge long before I suggest you get horrible service ..."

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