Historic Downtown District Hotels near Ashland

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Dec 17 - Dec 18
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Dec 18 - Dec 19
This weekend
Dec 19 - Dec 21
Next weekend
Dec 26 - Dec 28

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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, (1006)
"Small room but wonderful view and comfortable bed. "
United States
Jessica
The price is P5,653
P7,190 total
includes taxes & fees
Dec 18 - Dec 19
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, (1010)
"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 P6,171
P6,880 total
includes taxes & fees
Jan 2 - Jan 3, 2026
The Bard's Inn, BW Signature Collection by Best Western
Front of property
Winchester Inn

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 P10,511
P12,425 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, (579)
"The room was very clean, meals were excellent. Staff was excellent."
United States
Renae
McCall House Boutique Inn
Exterior
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, (108)
"Beautiful surroundings and hassle free check in. "
United States
Lynnesa
The price is P5,553
P7,127 total
includes taxes & fees
Dec 18 - Dec 19
Green Springs Inn
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 P11,333
P12,069 total
includes taxes & fees
Dec 28 - Dec 29
Resort at Eagle Point
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, (1003)
"Friendly staff and very clean"
United States
Noel
The price is P6,405
P7,142 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Best Western Windsor Inn
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
9.0 out of 10, Wonderful, (1499)
"A very great stay with our two dogs！"
United States
Yaolin
The price is P5,293
P6,564 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Ashland Hills Hotel & Suites
Interior detail
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, (495)
"Great family owned experience "
United States
Aliesje
The price is P3,438
P3,833 total
includes taxes & fees
Dec 23 - Dec 24
Relax Inn At Ashland
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, (1006)
"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 P6,111
P6,814 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Holiday Inn Express & Suites Ashland by IHG
Exterior
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, (1166)
"Beautiful place to stay "
United States
Daniel
The price is P6,114
P7,092 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Callahan's Mountain Lodge
Desk, blackout drapes, iron/ironing board, free WiFi
Scottish Inn

Scottish Inn

Scottish Inn
2.5 star property
3.9 km from Historic Downtown District
7.8 out of 10, Good, (666)
"Easy parking. Convenient to downtown and shopping"
United States
Michael
The price is P4,231
P4,717 total
includes taxes & fees
Dec 21 - Dec 22
Scottish Inn
Business center
Cedarwood Inn of Ashland

Cedarwood Inn of Ashland

Cedarwood Inn of Ashland
2.0 star property
3.1 km from Historic Downtown District
7.4 out of 10, Good, (1002)
"We’ve stayed here twice. Nice place for reasonable price."
United States
Mai
The price is P5,876
P6,551 total
includes taxes & fees
Dec 21 - Dec 22
Cedarwood Inn of Ashland
Seasonal outdoor pool, open 7:00 AM to 8:00 PM, pool umbrellas
Country Willows Inn and Estate

Country Willows Inn and Estate

Country Willows Inn and Estate
4.0 star property
4.1 km from Historic Downtown District
9.8 out of 10, Exceptional, (33)
"Beautiful setting close to downtown. Pool is marvelous!"
United States
Carol
Country Willows Inn and Estate
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, (1002)
"Room very good and vintage 70s style. "
United States
James P
The price is P3,649
P4,069 total
includes taxes & fees
Dec 18 - Dec 19
Timbers INN and Suites
Living area
The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges
4.0 star property
1.2 km from Historic Downtown District
10.0 out of 10, Exceptional, (7)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
The price is P9,516
P19,766 total
includes taxes & fees
Dec 21 - Dec 22
The Mountain Ave House by WanderLodges
Front of property
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, (1195)
"Huge room Great check in Very comfortable My 5th stay here "
United States
Michael L
The price is P3,702
P4,128 total
includes taxes & fees
Dec 19 - Dec 20
Flagship Inn of Ashland
Egyptian cotton sheets, desk, free WiFi, bed sheets
Ashland Motel - Oregon

Ashland Motel - Oregon

Ashland Motel - Oregon
2.0 star property
1.8 km from Historic Downtown District
7.8 out of 10, Good, (216)
"Great service "
United States
James
The price is P4,113
P4,586 total
includes taxes & fees
Dec 28 - Dec 29
Ashland Motel - Oregon
Seasonal outdoor pool
Palm Cottages

Palm Cottages

Palm Cottages
2.5 star property
1.6 km from Historic Downtown District
9.2 out of 10, Wonderful, (211)
"The room was not only spotless, but unique and very charming decor. It is like a little house and I wanted to stay another night just to enjoy reading in the little window nook!"
United States
Jennifer
The price is P8,931
P9,958 total
includes taxes & fees
Dec 18 - Dec 19
Palm Cottages
Front of property
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, (50)
"Nice hostel and clean rooms"
United States
EASWARAMOORTHI
The price is P2,274
P4,894 total
includes taxes & fees
Dec 28 - Dec 29
Ashland Commons Hostel
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.

Historic Railroad District

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

Siskiyou-Hargadine Historic District

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

Skidmore Academy Historic District

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.

Top Historic Downtown District Hotel Reviews

Super 8 by Wyndham Central Pt Medford

Super 8 by Wyndham Central Pt Medford

10/10 Excellent
"Great staff here stayed here before will stay again"
Celeste 1-night trip
Posted 3 days ago
Super 8 by Wyndham Central Pt Medford

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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 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 favorite 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 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.
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 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.