Historic Downtown District, OR

Ashland

Landmark building in Ashland Oregon.
Historic Downtown District
Historic Downtown District
Historic Downtown District
Historic Downtown District

Popular places to visit

Oregon Shakespeare Festival

Oregon Shakespeare Festival

4.5/5(268 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
USA, Oregon, Mt Ashland. Fresh snow on evergreens.

Mount Ashland Ski Area

4/5(71 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
A pretty male Wood Duck standing under the shade of a tree on the shoreline of a pond in a city park.

Lithia Park

4.5/5(484 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

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 acclaimed theater scene.

Allen Elizabethan Theatre

Thomas Theatre

4.5/5(82 reviews)

You can get tickets for a performance at Thomas Theatre on your trip to Ashland. Experience the area's lively festivals and entertainment choices.

Thomas Theatre

Historic Downtown District Hotel Deals

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
The price is ₩158,049 per night from Apr 6 to Apr 7
₩158,049
₩199,827 total
Apr 6 - Apr 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! (1,000 reviews)
Excellent location. Beautiful area. Close to an amazing park.

Reviewed on Apr 1, 2026

Ashland Springs Hotel
The Bard's Inn, BW Signature Collection by Best Western

The Bard's Inn, BW Signature Collection by Best Western

2.5 out of 5
132 N Main Street Ashland OR
The price is ₩143,710 per night from Apr 19 to Apr 20
₩143,710
₩160,236 total
Apr 19 - Apr 20
includes taxes & fees
Stay at this hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (1,005 reviews)
This is our favorite place to stay in Ashland. The location makes downtown restaurants, theaters and shops easily within walking distance. It is safe, has ample parking, the breakfast is very good and is always clean. I can highly recommend this place!

Reviewed on Apr 1, 2026

The Bard's Inn, BW Signature Collection by Best Western
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St. Ashland OR
The price is ₩343,946 per night from Apr 5 to Apr 6
₩343,946
₩404,072 total
Apr 5 - Apr 6
includes taxes & fees
Stay at this inn in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Oregon ...
9.6/10 Exceptional! (271 reviews)
Loved it! So cute!

Reviewed on Mar 31, 2026

Winchester Inn
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St Ashland OR
The price is ₩362,793 per night from Apr 5 to Apr 6
₩362,793
₩404,514 total
Apr 5 - Apr 6
includes taxes & fees
Stay at this B&B in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (593 reviews)
It has a great location, easy to walk to center of town. The breakfasts were very fresh and warm. They had 3 or 4 different EV chargers behind the lovely historic house.

Reviewed on Mar 31, 2026

McCall House Boutique Inn
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
The price is ₩149,745 per night from Apr 5 to Apr 6
₩149,745
₩166,973 total
Apr 5 - Apr 6
includes taxes & fees
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 ...
9.4/10 Exceptional! (1,735 reviews)
loved the hottub and glad that they stayed open late so that we can enjoy after a long drive.

Reviewed on Apr 2, 2026

Stratford Inn
Rogue Regency Inn Medford Airport

Rogue Regency Inn Medford Airport

3 out of 5
2300 Biddle Rd Medford OR
The price is ₩142,729 per night from Apr 8 to Apr 9
₩142,729
₩168,122 total
Apr 8 - Apr 9
includes taxes & fees
Book a stay at this business-friendly hotel in Medford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
8.8/10 Excellent! (2,912 reviews)
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Reviewed on Apr 2, 2026

Rogue Regency Inn Medford Airport
See all 699 properties in Historic Downtown 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.

Historic Downtown District, OR