Historic Downtown District

Ashland

Historic Downtown District
Photo by Shannon Willitts
Photo by Shannon Willitts
Photo by Shannon Willitts
Photo by Shannon Willitts

Popular places to visit

Things to do


Top hotels in Historic Downtown District

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
The price is €96 per night from 4 Jan to 5 Jan
€96
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this spa hotel in Ashland. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the breakfast and the helpful staff in their reviews. ...
9.2/10 Wonderful! (1,006 reviews)
Love this hotel! I am bummed they started charging for breakfast but it is delicious.

Reviewed on 15 Dec 2025

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
Fully refundableReserve now, pay when you stay
The price is €100 per night from 2 Jan to 3 Jan
€100
2 Jan - 3 Jan 2026
includes taxes & fees
Stay at this hotel in Ashland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. Popular ...
8.6/10 Excellent! (1,010 reviews)
Ok

Reviewed on 15 Dec 2025

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 €181 per night from 4 Jan to 5 Jan
€181
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this inn in Ashland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular attractions Oregon ...
9.6/10 Exceptional! (261 reviews)
Beautiful room with comfortable bed. Nice quality bedding.

Reviewed on 26 Oct 2025

Winchester Inn
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St Ashland OR
Stay at this B&B in Ashland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. Popular ...
9.8/10 Exceptional! (279 reviews)
We had a wonderful stay. Beautiful home with lovely decor. Staff were very attentive and friendly.

Reviewed on 15 Dec 2025

McCall House Boutique Inn
Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
2300 Biddle Rd Medford OR
The price is €82 per night from 11 Jan to 12 Jan
€82
11 Jan - 12 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Medford. Enjoy free breakfast, free Wi-Fi and a free airport shuttle. Our guests praise the breakfast and the pool in ...
8.8/10 Excellent! (2,698 reviews)
Staff

Reviewed on 14 Dec 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 €95 per night from 1 Jan to 2 Jan
€95
1 Jan - 2 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Ashland. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the helpful staff ...
8.8/10 Excellent! (1,496 reviews)
Great

Reviewed on 10 Dec 2025

Ashland Hills Hotel & Suites
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 neighbourhoods around Historic Downtown District

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Historic Railroad District

While Historic Railroad District isn't home to many top sights, Thomas Theatre and Oregon Shakespeare Festival are some notable places to visit nearby.

Historic Railroad District
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Siskiyou-Hargadine Historic District

If you're spending some time in Siskiyou-Hargadine Historic District, Lithia Park and Ashland Library are top sights worth seeing.

Siskiyou-Hargadine Historic District
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Skidmore Academy Historic District

While Skidmore Academy Historic District may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Thomas Theatre and Oregon Shakespeare Festival.

Skidmore Academy Historic District


Historic Downtown District

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