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 lively festivals 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

Allen Elizabethan Theatre

You can enjoy a show at Allen Elizabethan Theatre during your stay in Ashland. Wander around the area's picturesque gardens or experience its acclaimed theater scene.

Allen Elizabethan 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 449 per night from Apr 30 to May 1
SAR 449
SAR 707 total
includes taxes & fees
30 Apr - 1 May
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! (64 reviews)
A wonderful stay
"This is a charming old historic hotel, filled with beautiful antiques. It’s clean and comfortable, and the location is so convenient. There was easy parking on the street, but we really enjoyed walking to most things."

Reviewed on 22 April 2025

The Peerless Hotel by WanderLodges
Rogue Regency Inn and Suites
Rogue Regency Inn and Suites
3 out of 5
2300 Biddle Rd, Medford, OR
The price is SAR 405 per night from Apr 28 to Apr 29
SAR 405
SAR 456 total
includes taxes & fees
28 Apr - 29 Apr
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! (1,894 reviews)
"quiet"

Reviewed on 26 April 2025

Rogue Regency Inn and Suites
Ashland Hills Hotel & Suites
Ashland Hills Hotel & Suites
3 out of 5
2525 Ashland St, Ashland, OR
The price is SAR 436 per night from May 11 to May 12
SAR 436
SAR 523 total
includes taxes & fees
11 May - 12 May
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 ...
8.8/10 Excellent! (1,436 reviews)
Spotless
"Beautifully maintained mid century modern resort. Pool was not yet open when I visited. Easy parking and electric chargers. Dog friendly with fenced in excercise area at the back. Large, well maintained bedrooms with terrace or balcony. Great staff that are well trained and friendly."

Reviewed on 24 April 2025

Ashland Hills Hotel & Suites
Springhill Suites By Marriott Medford Airport
Springhill Suites By Marriott Medford Airport
3 out of 5
3519 HEATHROW WAY, Medford, OR
The price is SAR 435 per night from May 4 to May 5
SAR 435
SAR 490 total
includes taxes & fees
4 May - 5 May
Stay at this 3-star business-friendly hotel in Medford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9.4/10 Exceptional! (819 reviews)
"good"

Reviewed on 26 April 2025

Springhill Suites By Marriott Medford Airport
Stratford Inn
Stratford Inn
2.5 out of 5
555 Siskiyou Blvd, Ashland, OR
The price is SAR 413 per night from Apr 28 to Apr 29
SAR 413
SAR 460 total
includes taxes & fees
28 Apr - 29 Apr
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! (1,540 reviews)
"Friendly front desk. Spacious room with kitchenette."

Reviewed on 25 April 2025

Stratford Inn
Holiday Inn Express Hotel & Suites Medford-Central Point by IHG
Holiday Inn Express Hotel & Suites Medford-Central Point by IHG
2.5 out of 5
285 Peninger Rd, Central Point, OR
The price is SAR 334 per night from May 4 to May 5
SAR 334
SAR 376 total
includes taxes & fees
4 May - 5 May
Book a stay at this business-friendly hotel in Central Point. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,005 reviews)
"Good overall experience, only downside was the massive truck stop right next door"

Reviewed on 27 April 2025

Holiday Inn Express Hotel & Suites Medford-Central Point by IHG
See all 649 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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