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 ₹14,980 per night from 16 Aug to 17 Aug
₹14,980
₹21,905 total
16 Aug - 17 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 ₹14,984 per night from 19 Aug to 20 Aug
₹14,984
₹18,000 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 ...
9.6/10 Exceptional! (1,067 reviews)
"Was very loud on our floor, kids running up and down the hall and dogs barking. We dont recommend this place if youre looking for somewhere quiet."

Reviewed on 10 Aug 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 ₹9,254 per night from 6 Sept to 7 Sept
₹9,254
₹10,887 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. ...
8.8/10 Excellent! (3,211 reviews)
"This spot is underrated! A classic timeless cabin with all the amenities. The rooms are HUGE actually suites! The staff was nice, place was clean, breakfast was well maintained, and easy parking. All wins!"

Reviewed on 10 Aug 2026

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 ₹10,763 per night from 10 Sept to 11 Sept
₹10,763
₹10,925 total
10 Sept - 11 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 ...
8.8/10 Excellent! (1,028 reviews)
"The staff were just Wonderful! Jordan and Troy were so incredibly welcoming, friendly and helpful! Room was clean, peaceful and spacious. Bathroom was very clean."

Reviewed on 9 Aug 2026

Comfort Inn & Suites Ashland
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
The price is ₹12,308 per night from 7 Sept to 8 Sept
₹12,308
₹14,676 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 ...
8.8/10 Excellent! (1,525 reviews)
"convenient location"

Reviewed on 10 Aug 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 ₹9,483 per night from 16 Aug to 17 Aug
₹9,483
₹10,573 total
16 Aug - 17 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 ...
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