Historic Downtown District

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.
See properties

Things to do

An Audio Tour Through the Heart of Ashland, Oregon

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

P615
per adult
The Cultural Heart of Ashland: A Self-Guided Audio Tour
See all activities in Ashland

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 P10,354 per night from Aug 9 to Aug 10
P10,354
P11,545 total
Aug 9 - Aug 10
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! (1,002 reviews)
"Clean rooms, easy parking, walkable to downtown, helpful friendly staff."

Reviewed on Aug 3, 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 P11,519 per night from Aug 24 to Aug 25
P11,519
P13,828 total
Aug 24 - Aug 25
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! (1,009 reviews)
"Historic hotel, not really upgraded that much in the past 50 years. Breakfast is basic, with a voucher system that seems like a pointless hassle. The main advantage is superb location."

Reviewed on Aug 3, 2026

Ashland Springs Hotel
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St. Ashland OR
The price is P11,009 per night from Aug 10 to Aug 11
P11,009
P13,379 total
Aug 10 - Aug 11
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! (282 reviews)
"We had a wonderful time at the Winchester Inn! It’s an absolutely charming inn with a great location. Rooms and staff and breakfast were all fabulous. We will be back!"

Reviewed on Aug 2, 2026

Winchester Inn
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St Ashland OR
The price is P16,872 per night from Aug 9 to Aug 10
P16,872
P18,812 total
Aug 9 - Aug 10
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! (602 reviews)
"Staff was great!"

Reviewed on Jul 27, 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
The price is P10,421 per night from Aug 10 to Aug 11
P10,421
P12,459 total
Aug 10 - Aug 11
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 ...
9.6/10 Exceptional! (1,044 reviews)
"Staff was amazing, the property was fresh and bright, amenities were better than most facilities in the class. Will stay again"

Reviewed on Aug 3, 2026

Compass by Margaritaville in Medford
Rogue Regency Inn Medford Airport

Rogue Regency Inn Medford Airport

3 out of 5
2300 Biddle Rd Medford OR
Fully refundableReserve now, pay when you stay
The price is P6,010 per night from Aug 5 to Aug 6
P6,010
P7,067 total
Aug 5 - Aug 6
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! (3,186 reviews)
"Dated hotel… room had a musty smell. There was one person working reception and answering the phone with a long line of people waiting to check in. It was ok. Breakfast was ok, nothing special, nothing terrible."

Reviewed on Aug 3, 2026

Rogue Regency Inn Medford Airport
See all 697 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 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 rusted metal bridge in a forested area.

Historic Railroad District

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

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