Historic Railroad District, OR

Ashland

Photo by Inna Blair
Photo by Inna Blair

Popular places to visit

Ashland is probably best known for the Tony Award-winning Oregon Shakespeare Festival, which I highly recommend checking out if you're in to Shakespeare plays. The statue in the photo is actually a guy in a Shakespearean costume collecting contributions toward a permanent statue of the Bard in Ashland. #WeekendGetaway

Oregon Shakespeare Festival

4.5/5(265 reviews)

You can make plans for a show at Oregon Shakespeare Festival during your trip to Ashland. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants.

Oregon Shakespeare Festival
Being the tallest peak in the Siskiyou Mountains, Mt. Ashland offers excellent panoramic views, year round. The ski resort is relatively small, but the runs are steep and a few have cornice drops and chutes. It's a half hour drive from the town of Ashland in good weather. This photo was taken pre-season near the peak after a short yet strenuous ascent. #WeekendGetaway

Mount Ashland Ski Area

4/5(70 reviews)

Hit the slopes in Ashland with a visit to Mount Ashland Ski Area. Discover the top-notch restaurants and entertainment choices in this walkable area.

Mount Ashland Ski Area

Southern Oregon University

4.5/5(146 reviews)

Enjoy the collegiate vibe at Southern Oregon University as part of your travels around Ashland. Experience the area's acclaimed theater scene and entertainment choices.

Southern Oregon University

Lithia Park

4.5/5(481 reviews)

Explore the great outdoors at Lithia Park, a lovely green space in Ashland. Discover the top-notch restaurants and acclaimed theater scene in this family-friendly area.

Lithia Park

Howard Prairie Lake

Commune with nature and explore the great outdoors at Howard Prairie Lake during your travels in Ashland. While in this family-friendly area, you can savor the top-notch restaurants.

Howard Prairie Lake

Oregon Cabaret Theatre

4.5/5(47 reviews)

You can make plans for a show at Oregon Cabaret Theatre during your trip to Ashland. Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants.

Oregon Cabaret Theatre

Historic Railroad District Hotel Deals

The Peerless Hotel by WanderLodges
The Peerless Hotel by WanderLodges
2 out of 5
243 4th St, Ashland, OR
The price is SAR 591 per night from Mar 24 to Mar 25
SAR 591
SAR 857 total
includes taxes & fees
24 Mar - 25 Mar
Stay at this hotel in Ashland. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Ashland Library and Oregon Cabaret Theatre are ...
9.4/10 Exceptional! (61 reviews)
"This place was very clean and quiet. Absolutely the perfect romantic get away. Very conveniently located to really good restaurants."

Reviewed on 15 February 2025

The Peerless Hotel by WanderLodges
In the historic railroad district, walking distance to all the best of Ashland!
In the historic railroad district, walking distance to all the best of Ashland!
Ashland
Stay at this vacation home in Ashland. Enjoy a garden, tennis courts, and patios. Popular attractions Ashland Library and Oregon Cabaret Theatre are located ...
10/10 Exceptional! (168 reviews)
Nothing better in Ashland
"This small cozy house was perfect for our group over the Thanksgiving Holiday. Great kitchen with every item we needed. Cannot beat the location. We will be back."

Reviewed on 4 December 2024

Get rates
In the historic railroad district, walking distance to all the best of Ashland!
Rogue Regency Inn and Suites
Rogue Regency Inn and Suites
3 out of 5
2300 Biddle Rd, Medford, OR
Fully refundableReserve now, pay when you stay
The price is SAR 383 per night from Mar 13 to Mar 14
SAR 383
SAR 430 total
includes taxes & fees
13 Mar - 14 Mar
Book a stay at this business-friendly hotel in Medford. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
9/10 Wonderful! (1,796 reviews)
"Great place to stay with a great price for a weekend get away."

Reviewed on 9 March 2025

Rogue Regency Inn and Suites
Stratford Inn
Stratford Inn
2.5 out of 5
555 Siskiyou Blvd, Ashland, OR
The price is SAR 375 per night from Mar 19 to Mar 20
SAR 375
SAR 418 total
includes taxes & fees
19 Mar - 20 Mar
Book a stay at this business-friendly hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool ...
9.2/10 Wonderful! (1,525 reviews)
"The staff were exceptionally kind, friendly and helpful! They were the biggest contributor to our experience. Started and ended our stay with smiles. Excellent security."

Reviewed on 9 March 2025

Stratford Inn
Ashland Springs Hotel
Ashland Springs Hotel
3 out of 5
212 E Main St, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is SAR 545 per night from Mar 13 to Mar 14
SAR 545
SAR 627 total
includes taxes & fees
13 Mar - 14 Mar
Stay at this 3-star spa hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,003 reviews)
"Lovely accommodation and staff."

Reviewed on 11 March 2025

Ashland Springs Hotel
Ashland Hills Hotel & Suites
Ashland Hills Hotel & Suites
3 out of 5
2525 Ashland St, Ashland, OR
The price is SAR 442 per night from Mar 13 to Mar 14
SAR 442
SAR 530 total
includes taxes & fees
13 Mar - 14 Mar
Stay at this 3-star ski hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in ...
9/10 Wonderful! (1,443 reviews)
"Overall, for the price, this was a good place to stay. It seemed like many of the units are rented out long term for housing, so that gave it a feel of a "cheap motel." My key was deactivated on the second night and the guy at the front desk did not check my ID, just asked me to verify my name."

Reviewed on 6 March 2025

Ashland Hills Hotel & Suites
See all 637 properties in Historic Railroad District
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 neighborhoods around Historic Railroad District

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Historic Downtown District

5/5(133 area reviews)

If you're spending some time in Historic Downtown District, Allen Elizabethan Theatre and Oregon Shakespeare Festival are top sights worth seeing.

Historic Downtown District
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Siskiyou-Hargadine Historic District

4.5/5(12 area reviews)

While visiting Siskiyou-Hargadine Historic District, you might make a stop by sights like Ashland Library and Lithia Park.

Siskiyou-Hargadine Historic District
Walked across the street from the ER and imagine this was the view from a physician parking lot

Skidmore Academy Historic District

5/5(1 area review)

Skidmore Academy Historic District might not have many top sights, but Allen Elizabethan Theatre and Oregon Shakespeare Festival are two attractions nearby that you can check out.

Skidmore Academy Historic District

Historic Railroad District, OR

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