Historic Downtown District Hotels, Ashland

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Check prices for these dates

Tonight
29 Dec - 30 Dec
Tomorrow
30 Dec - 31 Dec
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

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Our top choices for Historic Downtown District hotels

Garden
Ashland Springs Hotel

Ashland Springs Hotel

Ashland Springs Hotel
3.0 star property
Historic Downtown District
9.2 out of 10, Wonderful, (1002)
"Small room but wonderful view and comfortable bed. "
United States
Jessica
The price is AU$167
includes taxes & fees
4 Jan - 5 Jan 2026
Ashland Springs Hotel
Lobby
The Bard's Inn, BW Signature Collection by Best Western

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

The Bard's Inn, BW Signature Collection by Best Western
2.5 star property
Historic Downtown District
8.6 out of 10, Excellent, (1001)
"The Bards Inn is lovely with each room themed after a Shakespe Play. Location is excellent just at the top of Main St. I can highly recommend this hotel"
United States
Suzanne
The price is AU$174
includes taxes & fees
11 Jan - 12 Jan 2026
The Bard's Inn, BW Signature Collection by Best Western
Bar (on property)
Winchester Inn

Winchester Inn

Winchester Inn
3.5 star property
Historic Downtown District
9.8 out of 10, Exceptional, (264)
"Beautiful B&B. This will now be our favorite stop in Ashland. "
United States
Willy
The price is AU$268
includes taxes & fees
1 Jan - 2 Jan 2026
Winchester Inn
Front of property
McCall House Boutique Inn

McCall House Boutique Inn

McCall House Boutique Inn
4.0 star property
Historic Downtown District
9.2 out of 10, Wonderful, (580)
"The room was very clean, meals were excellent. Staff was excellent."
United States
Renae
McCall House Boutique Inn
Free daily on-the-go breakfast
Flagship Inn of Ashland

Flagship Inn of Ashland

Flagship Inn of Ashland
2.5 star property
1.9 km from Historic Downtown District
8.8 out of 10, Excellent, (1207)
"Beautiful room and friendly staff. "
United States
Jackie
The price is AU$107
includes taxes & fees
11 Jan - 12 Jan 2026
Flagship Inn of Ashland
Exterior detail
Stratford Inn

Stratford Inn

Stratford Inn
2.5 star property
Siskiyou-Hargadine Historic District, 0.7 km from Historic Downtown District
9.4 out of 10, Exceptional, (1627)
"Great place to stay. The room was very nice and staff were great."
United States
Dane
The price is AU$134
includes taxes & fees
31 Dec - 1 Jan 2026
Stratford Inn
Exterior
Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG
2.5 star property
4.3 km from Historic Downtown District
9.2 out of 10, Wonderful, (1000)
"Friendly staff, easy, check-in, close parking, clean rooms, quiet. Good breakfast. Hot cakes, bacon, sausage, eggs, cinnamon rolls, yogurt everything you could want."
United States
Tiea
The price is AU$173
includes taxes & fees
10 Jan - 11 Jan 2026
Holiday Inn Express & Suites Ashland by IHG
Lobby sitting area
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites
3.0 star property
4.3 km from Historic Downtown District
8.8 out of 10, Excellent, (1500)
"What a great place to stay"
United States
christine
The price is AU$165
includes taxes & fees
1 Jan - 2 Jan 2026
Ashland Hills Hotel & Suites
Glamp Cottage Trailer | Living area
Paschal Winery

Paschal Winery

Paschal Winery
4.5 star property
8.1 km from Historic Downtown District
9.6 out of 10, Exceptional, (15)
"Very nice and hassle free check in "
United States
Matthew
The price is AU$311
includes taxes & fees
11 Jan - 12 Jan 2026
Paschal Winery
Exterior
Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland
2.5 star property
3.9 km from Historic Downtown District
8.8 out of 10, Excellent, (1012)
"Staff was excellent and very nice and room was clean and location is good Town is very cool 👍"
United States
Thomas
The price is AU$122
includes taxes & fees
25 Jan - 26 Jan 2026
Comfort Inn & Suites Ashland
Standard Room, 1 King Bed (Newly Redone)
Relax Inn At Ashland

Relax Inn At Ashland

Relax Inn At Ashland
1.5 star property
4.3 km from Historic Downtown District
6.8 out of 10, (499)
"Great family owned experience "
United States
Aliesje
The price is AU$106
includes taxes & fees
31 Dec - 1 Jan 2026
Relax Inn At Ashland
Front of property
Lithia Springs Resort

Lithia Springs Resort

Lithia Springs Resort
3.0 star property
3.6 km from Historic Downtown District
9.4 out of 10, Exceptional, (1000)
"Great stay, the room was great, very clean and bright. The breakfast buffet was awesome, also!"
United States
Denis
The price is AU$172
includes taxes & fees
4 Jan - 5 Jan 2026
Lithia Springs Resort
Outdoor dining
Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek
3.0 star property
0.4 km from Historic Downtown District
8.8 out of 10, Excellent, (1001)
"Nice stay again in Ashland amazing location for food and shopping! Love the local vibe. Comfortable bed and simple breakfast to start the day off right! "
United States
Brian
Plaza Inn & Suites at Ashland Creek
Hobart Peak | Terrace/patio
Green Springs Inn

Green Springs Inn

Green Springs Inn
2.0 star property
22.1 km from Historic Downtown District
9.4 out of 10, Exceptional, (109)
"Beautiful surroundings and hassle free check in. "
United States
Lynnesa
The price is AU$171
includes taxes & fees
11 Jan - 12 Jan 2026
Green Springs Inn
Garden
Ashland Commons Hostel

Ashland Commons Hostel

Ashland Commons Hostel
2.0 star property
0.8 km from Historic Downtown District
9.4 out of 10, Exceptional, (53)
"Nice hostel and clean rooms"
United States
EASWARAMOORTHI
The price is AU$117
includes taxes & fees
30 Dec - 31 Dec
Ashland Commons Hostel
Exterior
Best Western Windsor Inn

Best Western Windsor Inn

Best Western Windsor Inn
2.5 star property
4.3 km from Historic Downtown District
9.0 out of 10, Wonderful, (1001)
"Staff was incredibly friendly, kept the room clean and assisted us with food recommendations."
United States
Isaac
The price is AU$181
includes taxes & fees
11 Jan - 12 Jan 2026
Best Western Windsor Inn
Panoramic Room, 1 King Bed, Jetted Tub, Mountain View | Terrace/patio
Callahan's Mountain Lodge

Callahan's Mountain Lodge

Callahan's Mountain Lodge
3.0 star property
16.5 km from Historic Downtown District
8.8 out of 10, Excellent, (1173)
"Very friendly staff in a gorgeous setting! "
United States
Patrick
The price is AU$168
includes taxes & fees
6 Jan - 7 Jan 2026
Callahan's Mountain Lodge
Exterior
Resort at Eagle Point

Resort at Eagle Point

Resort at Eagle Point
3.5 star property
30.1 km from Historic Downtown District
9.4 out of 10, Exceptional, (265)
"Great place to stay! "
United States
Jeneen
The price is AU$167
includes taxes & fees
30 Dec - 31 Dec
Resort at Eagle Point
32-inch flat-screen TV with cable channels, TV
Wine Country Inn

Wine Country Inn

Wine Country Inn
3.0 star property
24.4 km from Historic Downtown District
9.4 out of 10, Exceptional, (1003)
"Courteous staff, very clean room, great breakfast assortment. Perfect location."
United States
Jeanne
The price is AU$164
includes taxes & fees
1 Jan - 2 Jan 2026
Wine Country Inn
Seasonal outdoor pool
Timbers INN and Suites

Timbers INN and Suites

Timbers INN and Suites
2.0 star property
2.3 km from Historic Downtown District
8.6 out of 10, Excellent, (1000)
"Courteous staff. Room was clean, and nice and hot for the winter cold outside. Plus, it's right next door to a great little pizza place!"
United States
Kevin
The price is AU$103
includes taxes & fees
30 Dec - 31 Dec
Timbers INN and 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.
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Our guide on where to stay in Historic Downtown District

Find the best Historic Downtown District areas for the activities you enjoy most.

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.

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.

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.

Top Historic Downtown District Hotel Reviews

Holiday Inn Express Hotel & Suites Medford-Central Point by IHG

Holiday Inn Express Hotel & Suites Medford-Central Point by IHG

10/10 Excellent
"Our room was as clean as one with many rooms to clean could make it. All of the staff were very friendly, and the breakfast was great. Premises seemed pretty safe as well. Would stay again."
Matt Allen 2-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Medford-Central Point by IHG

Frequently asked questions

What is Historic Downtown District like?
Travellers to Ashland's Historic Downtown District neighbourhood will be sure to enjoy a stay here. Make sure that you visit Allen Elizabethan Theatre and Oregon Shakespeare Festival as part of your Historic Downtown District travel plans.
What's the best accommodation in Historic Downtown District?
Based on Expedia customer reviews, Winchester Inn is the highest ranked property in Historic Downtown District. This inn offers free breakfast and a restaurant. Another favourite option in the neighbourhood is Ashland Springs Hotel.
How many hotels should I expect to find in the Historic Downtown District area?
If you're searching for places to stay in Ashland, Expedia has something to meet your needs with 29 Historic Downtown District hotels and other accommodation options to choose from.
If I need to cancel my hotel reservation in Historic Downtown District, will I receive a refund?
Yes, the majority of hotel room reservations are fully refundable as long as you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If your reservation is non-refundable, it may still be possible to cancel it and get a refund within a 24-hour period of booking. Enter dates in and click on "Search", then you can filter by "fully refundable" to get the best deals in Historic Downtown District.
What is there to do in this Ashland neighbourhood?
Historic Downtown District's sights and attractions like Allen Elizabethan Theatre, Angus Bowmer Theatre and Thomas Theatre offer insight into the local culture. As you're discovering the neighbourhood, Oregon Shakespeare Festival and Oregon Cabaret Theatre are some other places worth a visit. A few places to visit in the area around Historic Downtown District include Ashland Library, Lithia Park and Ashland Creek. While you're out sightseeing, North Mountain Park and ScienceWorks Hands-On Museum are a couple of additional sights to visit in Ashland.