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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, (1003)
"Small room but wonderful view and comfortable bed. "
United States
Jessica
The price is ￥13,558
￥17,458 total
includes taxes & fees
Jan 4 - Jan 5, 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 ￥16,421
￥18,309 total
includes taxes & fees
Jan 11 - Jan 12, 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 ￥24,122
￥28,638 total
includes taxes & fees
Jan 4 - Jan 5, 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
Exterior
Holiday Inn Express Hotel & Suites Medford-Central Point by IHG

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

Holiday Inn Express Hotel & Suites Medford-Central Point by IHG
2.5 star property
25 km from Historic Downtown District
9.0 out of 10, Wonderful, (1001)
"Clean room, check-in was quick "
United States
Karen
The price is ￥15,794
￥17,769 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Holiday Inn Express Hotel & Suites Medford-Central Point by IHG
Lobby lounge
Springhill Suites By Marriott Medford Airport

Springhill Suites By Marriott Medford Airport

Springhill Suites By Marriott Medford Airport
3.0 star property
23.3 km from Historic Downtown District
9.6 out of 10, Exceptional, (1019)
"Excellent place to stay with the family. Respectful and friendly staff."
United States
Ravi
The price is ￥17,157
￥19,301 total
includes taxes & fees
Jan 23 - Jan 24, 2026
Springhill Suites By Marriott Medford Airport
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, (1617)
"Great place to stay. The room was very nice and staff were great."
United States
Dane
Stratford 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, (1171)
"Very friendly staff in a gorgeous setting! "
United States
Patrick
The price is ￥14,563
￥17,122 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Callahan's Mountain Lodge
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, (1209)
"Beautiful room and friendly staff. "
United States
Jackie
The price is ￥9,971
￥11,118 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Flagship Inn of Ashland
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)
"We took advantage of the jacuzzi and the daily breakfast bar."
United States
Kirsten
The price is ￥12,646
￥12,836 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Comfort Inn & Suites Ashland
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, (1478)
"What a great place to stay"
United States
christine
The price is ￥14,248
￥17,635 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Ashland Hills Hotel & Suites
View from property
Fairfield Inn & Suites by Marriott Medford

Fairfield Inn & Suites by Marriott Medford

Fairfield Inn & Suites by Marriott Medford
2.5 star property
16.8 km from Historic Downtown District
9.4 out of 10, Exceptional, (505)
"Staff was friendly and room was clean. "
United States
David
The price is ￥18,560
￥20,881 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Fairfield Inn & Suites by Marriott Medford
Full-size fridge, stovetop, coffee/tea maker, toaster
My Place Hotel-Medford OR

My Place Hotel-Medford OR

My Place Hotel-Medford OR
3.0 star property
23.6 km from Historic Downtown District
9.2 out of 10, Wonderful, (1523)
"Staff was friendly and welcoming and we got a good nights sleep in a clean room."
United States
Jaselyn
The price is ￥13,771
￥15,492 total
includes taxes & fees
Jan 13 - Jan 14, 2026
My Place Hotel-Medford OR
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 ￥14,628
￥17,967 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Lithia Springs Resort
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, (1001)
"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 ￥16,264
￥18,133 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Holiday Inn Express & Suites Ashland by IHG
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, (1003)
"Really beautiful area, and so close to downtown. Very clean, large rooms. "
United States
Quinn
Plaza Inn & Suites at Ashland Creek
Indoor pool
Rogue Regency Inn Medford Airport

Rogue Regency Inn Medford Airport

Rogue Regency Inn Medford Airport
3.0 star property
21.9 km from Historic Downtown District
8.8 out of 10, Excellent, (2745)
"Tremendously friendly, great service, beautiful rooms and superb food. Love this hotel. "
United States
Ken
The price is ￥13,335
￥15,002 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Rogue Regency Inn Medford Airport
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, (1000)
"Staff was incredibly friendly, kept the room clean and assisted us with food recommendations."
United States
Isaac
The price is ￥17,045
￥19,006 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Best Western Windsor Inn
In-room safe, desk, soundproofing, iron/ironing board
Comfort Inn Medford North

Comfort Inn Medford North

Comfort Inn Medford North
2.5 star property
21.8 km from Historic Downtown District
8.4 out of 10, Very Good, (1007)
"I am checked in at Comfort Inn South."
United States
Patricia
The price is ￥10,867
￥12,445 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Comfort Inn Medford North
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 ￥9,686
￥10,799 total
includes taxes & fees
Jan 1 - Jan 2, 2026
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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Where to stay in Historic Downtown District

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

Siskiyou-Hargadine Historic District

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

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.

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.

Top Historic Downtown District Hotel Reviews

Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

10/10 Excellent
"Staff, good room, great mattresses. "
Nancy 1-night trip
Posted 2 days ago
Compass by Margaritaville in Medford

Frequently asked questions

What is Historic Downtown District like?
Travelers to Ashland's Historic Downtown District neighborhood will be sure to enjoy a stay in this neighborhood. Be sure to check out 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 favorite option in the neighborhood 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 accommodations to choose from.
If I need to cancel my hotel reservation in Historic Downtown District, will I receive a refund?
Yes! You'll find that most hotel bookings are fully refundable provided that you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If your reservation is non-refundable, it might still be possible to cancel it and be given a refund within 24 hours of booking. Enter your dates, click on "Search", then use the "fully refundable" filter to review the top deals on offer in Historic Downtown District.
Where can I learn more about changing or cancelling my trip to Historic Downtown District?
To find more details about picking new dates or cancelling your trip to Historic Downtown District, go to https://www.expedia.com/service/.
What is there to do in this Ashland neighborhood?
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 neighborhood, 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.