Historic Downtown District Travel Guide

Ashland

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

Popular places to visit


Top hotels in Historic Downtown District

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 2.879.499 ₫ per night from 1 Nov to 2 Nov
2.879.499 ₫
3.210.642 ₫ total
1 Nov - 2 Nov
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! (1,023 reviews)
"My favorite place to stay in Ashland. Clean and nice rooms, affordable, PERFECT location and great staff!"

Reviewed on 29 Sept 2025

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

Ashland Springs Hotel

3 out of 5
212 E Main St, Ashland, OR
The price is 6.932.353 ₫ per night from 8 Oct to 9 Oct
6.932.353 ₫
7.861.649 ₫ total
8 Oct - 9 Oct
includes taxes & fees
Stay at this 3-star 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 ...
9.2/10 Wonderful! (1,011 reviews)
"Second time staying at Ashland Springs. Came to the Oregon Shakespeare Festival for the weekend. Easy parking. Close to restaurants and shopping, very walkable. Great staff. Will be back again next year for sure!"

Reviewed on 28 Sept 2025

Ashland Springs Hotel
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St, Ashland, OR
The price is 4.511.021 ₫ per night from 1 Nov to 2 Nov
4.511.021 ₫
5.029.789 ₫ total
1 Nov - 2 Nov
includes taxes & fees
Stay at this 4-star 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. ...
9.8/10 Exceptional! (270 reviews)
Comfy, cozy and convenient
"Wonderful place in a very convenient location within easy walking distance of OSF and a range of food, drink and shopping. Very comfortable and cozy, with a friendly, helpful staff."

Reviewed on 30 Aug 2025

McCall House Boutique Inn
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St., Ashland, OR
The price is 5.159.906 ₫ per night from 27 Oct to 28 Oct
5.159.906 ₫
6.084.275 ₫ total
27 Oct - 28 Oct
includes taxes & fees
Stay at this 3.5-star inn in Ashland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular attractions ...
9.6/10 Exceptional! (253 reviews)
"Super comfortable room, great location to Main Street, excellent check in with friendly staff, would definitely stay here again!"

Reviewed on 16 Sept 2025

Winchester Inn
Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
2300 Biddle Rd, Medford, OR
The price is 2.852.820 ₫ per night from 5 Oct to 6 Oct
2.852.820 ₫
3.209.423 ₫ total
5 Oct - 6 Oct
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! (2,459 reviews)
"Decent. The older place, a bit worn but clean and on par for the price. Would stay again. They do have an on site restaurant, bar and pool."

Reviewed on 30 Sept 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 2.872.631 ₫ per night from 6 Oct to 7 Oct
2.872.631 ₫
3.467.233 ₫ total
6 Oct - 7 Oct
includes taxes & fees
Stay at this 3-star ski hotel in Ashland. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in ...
8.8/10 Excellent! (1,457 reviews)

Reviewed on 1 Oct 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, Oregon Cabaret Theatre and Allen Elizabethan Theatre 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 Allen Elizabethan Theatre and Oregon Shakespeare Festival.

Skidmore Academy Historic District