Historic Railroad District Travel Guide
Ashland
Visit Historic Railroad District
Top hotels in Historic Railroad District
The Peerless Hotel by WanderLodges
243 4th St Ashland OR
The price is ₹15,018 per night from 5 Oct to 6 Oct
₹15,018
₹21,960 total
5 Oct - 6 Oct
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
Compass by Margaritaville in Medford
2399 S Pacific Hwy Medford OR
The price is ₹14,518 per night from 12 Oct to 13 Oct
₹14,518
₹17,477 total
12 Oct - 13 Oct
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 ...
Red Lion Hotel Rogue Regency Medford Airport
2300 Biddle Rd Medford OR
The price is ₹8,812 per night from 16 Sept to 17 Sept
₹8,812
₹10,389 total
16 Sept - 17 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. ...
Best Western Windsor Inn
2520 Ashland St Ashland OR
The price is ₹10,739 per night from 21 Sept to 22 Sept
₹10,739
₹11,974 total
21 Sept - 22 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! (1,003 reviews)
"This was a charming place and we enjoyed the room a lot. However, we were in one of the rooms that could be conjoined with the room next to ours. Whoever was staying next to us showed up at midnight and was up until at least 5am and we could hear their entire conversation through the walls or door ..."
Reviewed on 11 Sept 2026
Ashland Hills Hotel & Suites
2525 Ashland St Ashland OR
The price is ₹12,494 per night from 21 Sept to 22 Sept
₹12,494
₹14,885 total
21 Sept - 22 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! (1,532 reviews)
"Very cool retro vibe. Half the property was painted, other half was not so looked a bit weird. Distance protocol signs indicating 6 feet of separation were still up in the pool area which was odd. Staff was not fully trained up and not super friendly or helpful. Would only stay for the crazy large ..."
Reviewed on 11 Sept 2026
Prospero's Flagship Inn
1193 Siskiyou Blvd Ashland OR
Fully refundableReserve now, pay when you stay
The price is ₹5,275 per night from 13 Sept to 14 Sept
₹5,275
₹5,882 total
13 Sept - 14 Sept
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! (1,444 reviews)
"The property was an excellent price. It was clean and well taken care of. The only problem I had was coming from a long trip from California, we got there an hour early. They wanted to charge us for wanting to check-in early, so we pretty much waited in the car until 3 PM. This is the only property ..."
Reviewed on 11 Sept 2026
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.
Photo by Shannon Willitts
Open Photo by Shannon Willitts
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.
