Ashland Hotel Guide. Hotels in Historic Downtown District, Ashland, United States of America

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Our top choices for Historic Downtown District hotels

Ashland Springs Hotel

Ashland Springs Hotel
3.0 star property
Historic Downtown District
9.2 out of 10, Wonderful, (1001)
"Small room but wonderful view and comfortable bed. "
United States
Jessica
The price is €96
includes taxes & fees
4 Jan - 5 Jan 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 star property
Historic Downtown District
8.6 out of 10, Excellent, (1002)
"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 €100
includes taxes & fees
2 Jan - 3 Jan 2026
The Bard's Inn, BW Signature Collection by Best Western

Winchester Inn

Winchester Inn
3.5 star property
Historic Downtown District
9.8 out of 10, Exceptional, (261)
"Super comfortable room, great location to Main Street, excellent check in with friendly staff, would definitely stay here again!"
United States
Laura
The price is €181
includes taxes & fees
4 Jan - 5 Jan 2026
Winchester 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

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, (1199)
"Beautiful room and friendly staff. "
United States
Jackie
The price is €71
includes taxes & fees
22 Dec - 23 Dec
Flagship Inn of Ashland

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, (1615)
"Great staff, clean, cute place. "
United States
Lynette
The price is €77
includes taxes & fees
24 Dec - 25 Dec
Stratford Inn

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 €192
includes taxes & fees
28 Dec - 29 Dec
Paschal Winery

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, (1508)
"What a great place to stay"
United States
christine
The price is €95
includes taxes & fees
1 Jan - 2 Jan 2026
Ashland Hills Hotel & Suites

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, (1001)
"Very nice property with nice decor. Room much nicer than competitors I’ve stayed with . Extremely clean, super staff. Will stay here again!"
United States
Christopher
The price is €99
includes taxes & fees
2 Jan - 3 Jan 2026
Holiday Inn Express & Suites Ashland by IHG

Relax Inn At Ashland

Relax Inn At Ashland
1.5 star property
4.3 km from Historic Downtown District
6.8 out of 10, (496)
"Great family owned experience "
United States
Aliesje
The price is €69
includes taxes & fees
22 Dec - 23 Dec
Relax Inn At 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, (1002)
"Staff was excellent and very nice and room was clean and location is good Town is very cool 👍"
United States
Thomas
The price is €72
includes taxes & fees
4 Jan - 5 Jan 2026
Comfort Inn & Suites Ashland

Lithia Springs Resort

Lithia Springs Resort
3.0 star property
3.6 km from Historic Downtown District
9.4 out of 10, Exceptional, (1003)
"This is an exceptional resort. It is a good value in beautiful surroundings. Friendly staff and a great breakfast for an additional $5. "
United States
Christine
The price is €98
includes taxes & fees
30 Dec - 31 Dec
Lithia Springs Resort

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, (1000)
"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

Wine Country Inn

Wine Country Inn
3.0 star property
24.4 km from Historic Downtown District
9.4 out of 10, Exceptional, (1000)
"Very friendly staff. Clean and comfortable. Only complaint is the walls are very thin. Loved this cute little town! "
United States
Jody
The price is €101
includes taxes & fees
1 Jan - 2 Jan 2026
Wine Country Inn

Green Springs Inn

Green Springs Inn
2.0 star property
22.1 km from Historic Downtown District
9.4 out of 10, Exceptional, (108)
"Beautiful surroundings and hassle free check in. "
United States
Lynnesa
The price is €104
includes taxes & fees
22 Dec - 23 Dec
Green Springs Inn

Ashland Commons Hostel

Ashland Commons Hostel
2.0 star property
0.8 km from Historic Downtown District
9.4 out of 10, Exceptional, (52)
"Nice hostel and clean rooms"
United States
EASWARAMOORTHI
The price is €63
includes taxes & fees
23 Dec - 24 Dec
Ashland Commons Hostel

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 €175
includes taxes & fees
22 Dec - 23 Dec
Resort at Eagle Point

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, (1002)
"Staff was incredibly friendly, kept the room clean and assisted us with food recommendations."
United States
Isaac
The price is €104
includes taxes & fees
2 Jan - 3 Jan 2026
Best Western Windsor Inn

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, (1168)
"Beautiful place to stay "
United States
Daniel
The price is €102
includes taxes & fees
19 Jan - 20 Jan 2026
Callahan's Mountain Lodge

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, (1001)
"Room very good and vintage 70s style. "
United States
James P
The price is €59
includes taxes & fees
24 Dec - 25 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.

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, Thomas Theatre and Oregon Shakespeare Festival 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 Thomas Theatre and Oregon Shakespeare Festival.

Top Historic Downtown District Hotel Reviews

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 Thomas 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. Other favourite options in the area include McCall House Boutique Inn and 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 30 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 Lithia Park are some other places worth a visit. A few places to visit in the area around Historic Downtown District include Oregon Cabaret Theatre, Ashland Library 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.