Historic Railroad District Travel Guide

Ashland

Mosby Creek Covered Bridge in Cottage Grove, Oregon, United States
Mosby Creek Covered Bridge in Cottage Grove, Oregon, United States
Wooden train bridge or trestle in lush forest area
Fort Vancouver National Historic Site
Road trip food!! I loved the burrito bowl (cafe inside!) and some of their grocery items. ✌️

The only downside was the trip from and back to the freeway... left, right, left, right. Way too many turns! We probably lost 20 minutes driving.

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! (99 reviews)
This historic hotel was everything we hoped for. Was very low key in a quiet neighborhood. The twin soaking tubs were perfect. It really felt like a trip back in time. We will definitely be back!

Reviewed on 22 Jan 2026

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! (2,813 reviews)
Accommodating staff

Reviewed on 2 Feb 2026

Rogue Regency Inn and Suites
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
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! (1,669 reviews)
Great location and easily walkable to anything and everything downtown!

Reviewed on 1 Feb 2026

Stratford Inn
Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
The price is ₹7,860 per night from 11 Feb to 12 Feb
₹7,860
₹10,120 total
11 Feb - 12 Feb
includes taxes & fees
Stay at this spa hotel in Ashland. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the breakfast and the helpful staff in their reviews. ...
9.2/10 Wonderful! (1,000 reviews)
We upgraded and that was not wise. The rooms are extremely small. The upgrade was not worth the $ as we viewed 3 rooms before choosing one. The Hotel is a classic, historical center of quaint Ashland. Good staffstaff

Reviewed on 27 Jan 2026

Ashland Springs Hotel
Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
2399 S Pacific Hwy Medford OR
The price is ₹13,730 per night from 17 Feb to 18 Feb
₹13,730
₹16,529 total
17 Feb - 18 Feb
includes taxes & fees
Stay at this golf hotel in Medford. Enjoy free breakfast, free parking and a 24-hour fitness centre. Our guests praise the breakfast and the pool in their reviews. ...
9.6/10 Exceptional! (1,003 reviews)
Best Front desk EVER!

Reviewed on 2 Feb 2026

Compass by Margaritaville in Medford
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
The price is ₹8,575 per night from 6 Feb to 7 Feb
₹8,575
₹10,464 total
6 Feb - 7 Feb
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! (1,466 reviews)
Front desk staff were very helpful and gave us a nice room with direct access to the lawn for our four-legged companion. Room was clean though the light over the round coffee table gave everything a greenish hue. I suggest you change that to a better modern one.

Reviewed on 29 Jan 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.

Other neighbourhoods around Historic Railroad District

Landmark building in Ashland Oregon.

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
Street scene in downtown Ashland Oregon state.

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
Aerial view of Ashland, Oregon

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