Historic Downtown District, OR

Ashland

A historic building with a classical facade, a person standing on the steps, and a wheelchair-accessible sign.
A display window with a large red flower and a sign reading "Oregon Shakespeare Festival Welcome Center".
A building corner with ornate architectural details and arched windows overlooking a cityscape.
A detailed bronze sculpture of a group of people, some with raised hands, against a tiled wall.
A street with a 'NO PARKING' sign, a 'VARNS' sign, and a 'JEWEL BOX' storefront.

Stay near popular Historic Downtown District attractions

Oregon Shakespeare Festival

9.2/10 (620 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.
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Things to do

An Audio Tour Through the Heart of Ashland, Oregon

The Cultural Heart of Ashland: A Self-Guided Audio Tour

￥1,567
per adult
The Cultural Heart of Ashland: A Self-Guided Audio Tour
See all activities in Ashland

Historic Downtown District Hotel Deals

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 ￥18,230 per night from Nov 19 to Nov 20
￥18,230
￥20,327 total
Nov 19 - Nov 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 ...
8.4/10 Very Good! (1,007 reviews)
"Location is very convenient to nice walks, restaurants and shops."

Reviewed on Oct 20, 2026

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 ￥14,833 per night from Nov 19 to Nov 20
￥14,833
￥19,001 total
Nov 19 - Nov 20
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! (1,004 reviews)
"Location is perfect for Ashland."

Reviewed on Oct 19, 2026

Ashland Springs Hotel
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St. Ashland OR
The price is ￥21,108 per night from Nov 9 to Nov 10
￥21,108
￥26,058 total
Nov 9 - Nov 10
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! (291 reviews)
"Amazing breakfasts, friendly staff, best location"

Reviewed on Oct 10, 2026

Winchester Inn
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St Ashland OR
The price is ￥24,745 per night from Nov 1 to Nov 2
￥24,745
￥27,590 total
Nov 1 - Nov 2
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! (618 reviews)
"Our favorite hotel In Ashland. It is probably the most beautiful building in Ashland and the rooms and the amenities are first class. We recommend this place to everyone."

Reviewed on Oct 13, 2026

McCall House Boutique Inn
Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
2399 S Pacific Hwy Medford OR
Fully refundableReserve now, pay when you stay
The price is ￥19,948 per night from Nov 8 to Nov 9
￥19,948
￥24,337 total
Nov 8 - Nov 9
includes taxes & fees
Book a stay at this golf hotel in Medford. Enjoy free breakfast, free parking, and a casino. Our guests praise the breakfast and the pool in our reviews. Popular ...
Compass by Margaritaville in Medford
Red Lion Hotel Rogue Regency Medford Airport

Red Lion Hotel Rogue Regency Medford Airport

3 out of 5
2300 Biddle Rd Medford OR
The price is ￥14,641 per night from Oct 21 to Oct 22
￥14,641
￥17,261 total
Oct 21 - Oct 22
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 ...
Red Lion Hotel Rogue Regency Medford Airport
See all 674 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.

Where to stay in Historic Downtown District

Find the best Historic Downtown District areas and neighborhoods for the activities you enjoy most.
A rusted metal bridge in a forested area.

Historic Railroad District

Historic Railroad District might not have many top sights, but Oregon Cabaret Theatre and Allen Elizabethan Theatre are two attractions nearby that you can check out.

A tree-lined street with a mountain backdrop.

Siskiyou-Hargadine Historic District

While visiting Siskiyou-Hargadine Historic District, you might make a stop by sights like Lithia Park and Ashland Library.

A town with buildings and trees in autumn colors, surrounded by mountains.

Skidmore Academy Historic District

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.

Historic Downtown District, OR