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.

Things to do


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 ฿5,065 per night from 10 Aug to 11 Aug
฿5,065
฿7,454 total
10 Aug - 11 Aug
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! (111 reviews)
"My wife and I stayed in the anniversary suite. We loved the tubs and all of the decor was fantastic"

Reviewed on 9 Aug 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 ฿5,203 per night from 19 Aug to 20 Aug
฿5,203
฿6,250 total
19 Aug - 20 Aug
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 ...
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 ฿3,214 per night from 6 Sept to 7 Sept
฿3,214
฿3,781 total
6 Sept - 7 Sept
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. ...
Rogue Regency Inn Medford Airport
Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

2.5 out of 5
434 S. Valley View Rd. Ashland OR
The price is ฿3,766 per night from 8 Sept to 9 Sept
฿3,766
฿3,822 total
8 Sept - 9 Sept
includes taxes & fees
Stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
Comfort Inn & Suites Ashland
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
The price is ฿4,274 per night from 7 Sept to 8 Sept
฿4,274
฿5,096 total
7 Sept - 8 Sept
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 ...
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 ฿2,946 per night from 10 Aug to 11 Aug
฿2,946
฿3,285 total
10 Aug - 11 Aug
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! (1,414 reviews)
"Good value for the money! Clean and well maintained."

Reviewed on 9 Aug 2026

Prospero's Flagship 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.

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 Thomas 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 Thomas Theatre.



Historic Railroad District Travel Guide