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 ₹16,907 per night from 30 Jun to 1 Jul
₹16,907
₹20,154 total
30 Jun - 1 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! (1,006 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! (3,138 reviews)
"All of the staff was incredibly helpful and friendly. The room was clean! Breakfast was very nice and hot . We had a large pickup truck and found enough room to park it as well. We will definitely return!"

Reviewed on 28 Jun 2026

Rogue Regency Inn Medford Airport
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
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 ...
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 ₹8,270 per night from 29 Jun to 30 Jun
₹8,270
₹9,221 total
29 Jun - 30 Jun
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! (1,375 reviews)
"The room was clean, but small. The shower was really small. The staff were friendly. We did not like the breakfast. The blow dryer was broken."

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! (1,575 reviews)
"Actually really clean for the price. It’s definitely not anything fancy but it was ok for what we needed. Front desk staff appearance was a little off putting as some of the receptionists didn’t appear to be well groomed and had an odor. There is zero kitchen equipment which was a downer but wal ..."

Reviewed on 28 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, Ashland Library and Lithia Park 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