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 ₹11,958 per night from 30 Aug to 31 Aug
₹11,958
₹18,553 total
30 Aug - 31 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! (112 reviews)
"The place was cute. Room was really nice and bed was comfy. Close to downtown. Would stay there again."

Reviewed on 13 Aug 2026

The Peerless Hotel by WanderLodges
Rogue Regency Inn Medford Airport

Rogue Regency Inn Medford Airport

3 out of 5
2300 Biddle Rd Medford OR
Fully refundableReserve now, pay when you stay
The price is ₹11,354 per night from 8 Sept to 9 Sept
₹11,354
₹13,251 total
8 Sept - 9 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
Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
2399 S Pacific Hwy Medford OR
The price is ₹15,392 per night from 6 Sept to 7 Sept
₹15,392
₹18,463 total
6 Sept - 7 Sept
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! (1,076 reviews)
"I needed a hotel for one night on a road trip and randomly found this property. It was absolutely bizarre to feel like you were in the Florida Keys on a tropical vacation when you were in fact in Medford, OR., but I was not angry about it. The pool was fantastic, the bar/restaurant service was top-notch ..."

Reviewed on 28 Aug 2026

Compass by Margaritaville in Medford
Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

2.5 out of 5
434 S. Valley View Rd. Ashland OR
The price is ₹10,070 per night from 28 Sept to 29 Sept
₹10,070
₹10,221 total
28 Sept - 29 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
Best Western Windsor Inn

Best Western Windsor Inn

2.5 out of 5
2520 Ashland St Ashland OR
The price is ₹10,750 per night from 7 Sept to 8 Sept
₹10,750
₹11,986 total
7 Sept - 8 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 ...
9/10 Wonderful! (1,001 reviews)
"Our first stay. We found the property well-located for activities in downtown Ashland with adequate safe parking. The staff was available without being intrusive. Ryan was particularly helpful. Our room was quiet, clean and furnished as advertised, no surprises. One of the most organized and comfortable ..."

Reviewed on 28 Aug 2026

Best Western Windsor Inn
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
The price is ₹9,946 per night from 1 Sept to 2 Sept
₹9,946
₹12,045 total
1 Sept - 2 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 ...
8.8/10 Excellent! (1,531 reviews)
"This was a very nice stop. Close to many things."

Reviewed on 28 Aug 2026

Ashland Hills Hotel & Suites
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 Oregon Shakespeare Festival.

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 Oregon Shakespeare Festival.



Historic Railroad District Travel Guide