Historic Downtown District, OR

Ashland

Landmark building in Ashland Oregon.
Landmark building in Ashland Oregon.
Ashland is all about the Shakespeare down to the poppy #Red
We had a corner queen on the 8th floor and this is a close look at the neoclassical gothic architecture from our bedroom window
I always check out the local chamber of commerce when I land in a town I haven’t been to before. Ashland Oregon Chamber of Commerce is unique in that it’s beside this amazing bronze Shakespeare statue.

Popular places to visit

Ashland is probably best known for the Tony Award-winning Oregon Shakespeare Festival, which I highly recommend checking out if you're in to Shakespeare plays. The statue in the photo is actually a guy in a Shakespearean costume collecting contributions toward a permanent statue of the Bard in Ashland. #WeekendGetaway

Oregon Shakespeare Festival

4.5/5(265 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(70 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(481 reviews)

Explore the great outdoors at Lithia Park, a lovely green space in Ashland. Discover the top-notch restaurants and acclaimed theater scene 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

Thomas Theatre

4.5/5(81 reviews)

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

Thomas 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 lively festivals.

Allen Elizabethan Theatre

Things to do

Salem Puzzling Adventure

Ashland Puzzling Adventure

￥5,526
per traveler
Ashland Puzzling Adventure
See all activities in Ashland

Historic Downtown District Hotel Deals

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
The price is ￥13,274 per night from Feb 16 to Feb 17
￥13,274
￥17,091 total
Feb 16 - Feb 17
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! (1,019 reviews)
This place is beautiful!

Reviewed on Feb 9, 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 ￥15,119 per night from Feb 16 to Feb 17
￥15,119
￥16,858 total
Feb 16 - Feb 17
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! (1,001 reviews)
Nice beds, clean room.

Reviewed on Feb 11, 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 ￥27,498 per night from Feb 15 to Feb 16
￥27,498
￥32,496 total
Feb 15 - Feb 16
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! (270 reviews)
The room is fantastic!! Highly recommend!

Reviewed on Jan 15, 2026

Winchester Inn
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St Ashland OR
The price is ￥22,604 per night from Feb 16 to Feb 17
￥22,604
￥25,204 total
Feb 16 - Feb 17
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 ...
9.8/10 Exceptional! (284 reviews)
Great place, quite and very helpful and friendly staff

Reviewed on Feb 4, 2026

McCall House Boutique Inn
Spacious 2 bedroom historic home with two king beds and kitchenette.

Spacious 2 bedroom historic home with two king beds and kitchenette.

Ashland OR
The price is ￥24,432 per night from Feb 15 to Feb 16
￥24,432
￥53,311 total
Feb 15 - Feb 16
includes taxes & fees
Stay at this apartment in Ashland. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Allen Elizabethan Theatre and Angus Bowmer ...
10/10 Exceptional! (3 reviews)
Excellent location
Great location, nice place to stay. Could use a frying pan.

Reviewed on Apr 22, 2025

Spacious 2 bedroom historic home with two king beds and kitchenette.
Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
2300 Biddle Rd Medford OR
Book a stay at this business-friendly hotel in Medford. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
8.8/10 Excellent! (2,829 reviews)
Clean and very helpful

Reviewed on Feb 11, 2026

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Rogue Regency Inn and Suites
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.

Other neighborhoods around Historic Downtown District

Mosby Creek Covered Bridge in Cottage Grove, Oregon, United States

Historic Railroad District

4.5/5(7 area reviews)

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

Historic Railroad District
Street scene in downtown Ashland Oregon state.

Siskiyou-Hargadine Historic District

4.5/5(12 area reviews)

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

Siskiyou-Hargadine Historic District
Aerial view of Ashland, Oregon

Skidmore Academy Historic District

5/5(1 area review)

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

Skidmore Academy Historic District

Historic Downtown District, OR