Historic Railroad District, OR

Ashland

Road trip food!! I loved the burrito bowl (cafe inside!) and some of their grocery items. ✌️ The only downside was the trip from and back to the freeway... left, right, left, right. Way too many turns! We probably lost 20 minutes driving.
Road trip food!! I loved the burrito bowl (cafe inside!) and some of their grocery items. ✌️ The only downside was the trip from and back to the freeway... left, right, left, right. Way too many turns! We probably lost 20 minutes driving.

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
Looks more like a little square in Nottingham Hill than Oregon. Lovely town with festive holiday lights at night.

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 entertainment choices in this family-friendly area.

Lithia Park

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 entertainment choices and acclaimed theater scene.

Southern Oregon University

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

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

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 Ashland Library and Oregon Cabaret Theatre are ...
9.6/10 Exceptional! (97 reviews)
Couldn't be better. Excellent place to stay.

Reviewed on 2026/1/19

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The Peerless Hotel by WanderLodges
Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
2300 Biddle Rd Medford OR
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! (2,786 reviews)
Very friendly staff and comfortable room. We also enjoyed the breakfast.

Reviewed on 2026/1/20

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Rogue Regency Inn and Suites
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
Stay at this hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular ...
9.2/10 Wonderful! (1,637 reviews)
Great location in Ashland with a Safeway across the street.

Reviewed on 2026/1/16

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Stratford Inn
Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
The price is NT$2,470 per night from Feb 6 to Feb 7
NT$2,470
NT$3,229 total
Feb 6 - Feb 7
includes taxes & fees
Book a stay at this spa hotel in Ashland. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the breakfast and the helpful staff in our ...
9.2/10 Wonderful! (1,003 reviews)
Wonderful staff, great views, the rooms was clean with spa quality toiletries.

Reviewed on 2026/1/15

Ashland Springs Hotel
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
The price is NT$2,668 per night from Jan 22 to Jan 23
NT$2,668
NT$3,291 total
Jan 22 - Jan 23
includes taxes & fees
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 helpful ...
8.8/10 Excellent! (1,473 reviews)
No free breakfast was disappointing. The room was very nice and clean though.

Reviewed on 2026/1/18

Ashland Hills Hotel & Suites
Motel 6 Medford, OR - North

Motel 6 Medford, OR - North

2 out of 5
2400 Biddle Rd Medford OR
Fully refundableReserve now, pay when you stay
The price is NT$1,153 per night from Jan 27 to Jan 28
NT$1,153
NT$1,298 total
Jan 27 - Jan 28
includes taxes & fees
Stay at this motel in Medford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.2/10 Good! (1,085 reviews)
Nice staff

Reviewed on 2026/1/11

Motel 6 Medford, OR - North
See all 702 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

Ashland is all about the Shakespeare down to the poppy #Red

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 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