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 lively festivals 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

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 entertainment choices.

Allen Elizabethan Theatre

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

Historic Railroad District Hotel Deals

The Peerless Hotel by WanderLodges
The Peerless Hotel by WanderLodges
2 out of 5
243 4th St, Ashland, OR
Stay at this hotel in Ashland. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Oregon Shakespeare Festival and Ashland Library ...
9.4/10 Exceptional! (71 reviews)
Uniquely charming
"Great historic hotel. If you're looking for modern amenities this is not it. But antiques, charm and a unique experience this is it. Don't expect anyone to carry your luggage or have a lot of bathroom space. Just small, quaint and memorable"

Reviewed on 2025/7/2

Get rates
The Peerless Hotel by WanderLodges
Hanna's House by WanderLodges
Hanna's House by WanderLodges
4 out of 5
39 4th St, Ashland, OR
The price is NT$4,204 per night from Jul 28 to Jul 29
NT$4,204
NT$6,973 total
Jul 28 - Jul 29
includes taxes & fees
Stay at this 4-star business-friendly vacation home in Ashland. Enjoy free WiFi, free parking, and a garden. Popular attractions Oregon Shakespeare Festival ...
"If I were single I could live here. It's that comfortable. The freestanding apartment is ideally located and finished to a very high standard. Amazingly well designed and laid out. Full kitchen, living room, bedroom, and bath. Many, many conveniences. Cafe table in garden outside. We parked once ..."

Reviewed on 2024/9/19

Hanna's House by WanderLodges
232 4th Street
232 4th Street
3 out of 5
232 4th Street, Ashland, OR
Stay at this 3-star apartment in Ashland. Enjoy free parking. Popular attractions Oregon Shakespeare Festival and Ashland Library are located nearby.
Great location
"Great location with easy access to downtown Ashland. We were able to walk nearly everywhere we wanted to go and enjoyed the neighborhood shops. Overall the neighborhood was quiet and the accommodations were what we wanted."

Reviewed on 2024/3/30

Get rates
232 4th Street
Rogue Regency Inn and Suites
Rogue Regency Inn and Suites
3 out of 5
2300 Biddle Rd, Medford, OR
The price is NT$3,124 per night from Aug 1 to Aug 2
NT$3,124
NT$3,514 total
Aug 1 - Aug 2
includes taxes & fees
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 ...
8.8/10 Excellent! (2,084 reviews)
"Older hotel but still nice. Larger rooms than many hotels I’ve stayed at. The breakfast was either not very good or there was no food when we went."

Reviewed on 2025/7/7

Rogue Regency Inn and Suites
Quality Inn & Suites Medford Airport
Quality Inn & Suites Medford Airport
2.5 out of 5
1950 Biddle Rd, Medford, OR
The price is NT$2,581 per night from Aug 5 to Aug 6
NT$2,581
NT$2,919 total
Aug 5 - Aug 6
includes taxes & fees
Book a stay at this spa hotel in Medford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.4/10 Very Good! (1,012 reviews)
"It’s Quality Inn, which is t one of the larger, more prominent chains, but it was a great, clean, easy to navigate room and checked all the boxes a hotel should. Would definitely stay here again."

Reviewed on 2025/7/6

Quality Inn & Suites 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 NT$2,746 per night from Aug 3 to Aug 4
NT$2,746
NT$2,787 total
Aug 3 - Aug 4
includes taxes & fees
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (1,006 reviews)
"this is a very nice motel. Friendly, clean, comfortable, good free breakfast. Good price. Close to town. We will stay again."

Reviewed on 2025/7/5

Comfort Inn & Suites Ashland
See all 662 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 Angus Bowmer Theatre 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 Lithia Park and Ashland Library.

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