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Check prices for these dates

This weekend
May 29 - May 31
Next weekend
Jun 5 - Jun 7

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Our top choices for Historic Downtown District hotels

Front of property

Winchester Inn

Winchester Inn
3.5 star property
Historic Downtown District
9.6 out of 10, Exceptional, (275 reviews)
"Lovely establishment, made to order breakfast, easy walking to theaters. "
United States
Peter
The price is ￥45,472
￥54,321 total
includes taxes & fees
Jun 8 - Jun 9
Winchester Inn
Garden

Ashland Springs Hotel

Ashland Springs Hotel
3.0 star property
Historic Downtown District
9.2 out of 10, Wonderful, (1,008 reviews)
"Loved the location and elegant vintage architecture! "
United States
Kim
The price is ￥20,836
￥25,740 total
includes taxes & fees
May 31 - Jun 1
Ashland Springs Hotel
Front of property

McCall House Boutique Inn

McCall House Boutique Inn
4.0 star property
Historic Downtown District
9.2 out of 10, Wonderful, (594 reviews)
"McCall House was a perfect place to stay for an overnight trip to Ashland. The location was perfect and easy walking distance to many restaurants. The property was very quite. The breakfast was delicious. "
United States
John
The price is ￥42,052
￥46,888 total
includes taxes & fees
Jun 2 - Jun 3
McCall House Boutique Inn
Lobby

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, (1,007 reviews)
"Conveniently located to downtown."
United States
Katelin
The price is ￥20,546
￥22,909 total
includes taxes & fees
May 31 - Jun 1
The Bard's Inn, BW Signature Collection by Best Western
Front of property

Hummingbird Estate Wine & Suites

Hummingbird Estate Wine & Suites
4.5 star property
25.8 km from Historic Downtown District
9.6 out of 10, Exceptional, (159 reviews)
"A lovely quaint place to stay with great wine and kind staff - would absolutely recommend. Most rooms additionally have a separated sitting room away from the bedroom which is a nice thing to have. Plus the ground are gorgeous and wandering around at sunset is amazing!"
United States
Laurette
The price is ￥26,931
￥27,335 total
includes taxes & fees
Jun 23 - Jun 24
Hummingbird Estate Wine & Suites
Seasonal outdoor pool, open 7:00 AM to 8:00 PM, pool umbrellas

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, (37 reviews)
"Excellent Breakfast Room and lovely breakfast Staff was perfect ....... Enjoyed the entire experience 😎"
United States
Steve
The price is ￥40,352
￥40,957 total
includes taxes & fees
May 28 - May 29
Country Willows Inn and Estate
Exterior

Resort at Eagle Point

Resort at Eagle Point
3.5 star property
30.2 km from Historic Downtown District
9.4 out of 10, Exceptional, (276 reviews)
"Was a great stay "
United States
Rendy
The price is ￥27,338
￥29,115 total
includes taxes & fees
May 28 - May 29
Resort at Eagle Point
Front of property

Lithia Springs Resort

Lithia Springs Resort
3.0 star property
3.6 km from Historic Downtown District
9.4 out of 10, Exceptional, (1,006 reviews)
"Great amenities, very comfortable rooms, pretty spot. "
United States
Willy
The price is ￥26,351
￥29,931 total
includes taxes & fees
May 31 - Jun 1
Lithia Springs Resort
Exterior

Abigail’s Bed & Breakfast Inn

Abigail’s Bed & Breakfast Inn
3.5 star property
Skidmore Academy Historic District, 1 km from Historic Downtown District
9.4 out of 10, Exceptional, (62 reviews)
"Best B and B in Ashland we have ever stayed at in thirty years . Amazing food and very comfortable."
United States
Andrew
The price is ￥41,322
￥46,074 total
includes taxes & fees
May 29 - May 30
Abigail’s Bed & Breakfast Inn
Exterior

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, (1,153 reviews)
"we always enjoyed staying here. Love the ribeye and friendly staff. "
United States
Chunrong
The price is ￥21,947
￥24,665 total
includes taxes & fees
May 28 - May 29
Callahan's Mountain Lodge
Exterior

Lady Geneva Bed and Breakfast

Lady Geneva Bed and Breakfast
3.5 star property
19.2 km from Historic Downtown District
10.0 out of 10, Exceptional, (73 reviews)
"The owners were fantastic! Would recommend you stay here if you get a chance!"
United States
Donna
The price is ￥30,419
￥34,221 total
includes taxes & fees
May 28 - May 29
Lady Geneva Bed and Breakfast
Property amenity

Fairfield Inn & Suites by Marriott Medford

Fairfield Inn & Suites by Marriott Medford
3.0 star property
16.8 km from Historic Downtown District
9.6 out of 10, Exceptional, (565 reviews)
"Very clean and new hotel at the time of stay."
United States
chad
The price is ￥20,502
￥23,066 total
includes taxes & fees
Jun 7 - Jun 8
Fairfield Inn & Suites by Marriott Medford
Exterior

Green Springs Inn

Green Springs Inn
2.0 star property
22.1 km from Historic Downtown District
9.2 out of 10, Wonderful, (125 reviews)
"Very clean, comfortable room in the lodge. Gorgeous setting."
United States
Mary
The price is ￥13,002
￥17,230 total
includes taxes & fees
May 28 - May 29
Green Springs Inn
Glamp Cottage Trailer | Living area | Flat-screen TV, fireplace

Paschal Winery

Paschal Winery
4.5 star property
8.1 km from Historic Downtown District
9.8 out of 10, Exceptional, (18 reviews)
"Incredible experience, fabulous wine, wish we had stayed longer to soak in the beauty of the experience. "
United States
Frankie
The price is ￥20,397
￥44,543 total
includes taxes & fees
Jun 14 - Jun 15
Paschal Winery
Lobby sitting area

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, (1,476 reviews)
"Great place"
United States
Eddie
The price is ￥18,490
￥22,209 total
includes taxes & fees
May 31 - Jun 1
Ashland Hills Hotel & Suites
View from property

Courtyard by Marriott Medford Airport

Courtyard by Marriott Medford Airport
3.0 star property
23.5 km from Historic Downtown District
9.0 out of 10, Wonderful, (895 reviews)
"Staff were very friendly. Room was large and comfortable. "
United States
Joe
The price is ￥21,524
￥24,353 total
includes taxes & fees
Jun 14 - Jun 15
Courtyard by Marriott Medford Airport
Sundeck

Grandview of Ashland

Grandview of Ashland
3.0 star property
1.8 km from Historic Downtown District
10.0 out of 10, Exceptional, (7 reviews)
"Grandview of Ashland was a beautiful home!! It was super clean and the views of the valley were amazing. Our entire party had a wonderful time and would 100% stay there again. Highly recommend!"
United States
Paul
The price is ￥55,243
￥88,173 total
includes taxes & fees
Jun 7 - Jun 8
Grandview of Ashland
Garden view

Arden Forest Inn

Arden Forest Inn
4.0 star property
0.8 km from Historic Downtown District
9.8 out of 10, Exceptional, (104 reviews)
"Lovely property hidden in a quiet neighborhood, walking distance to downtown and Oregon Shakespeare Theatre. Could use a quieter bathroom fan but all else good!"
United States
Mary Lee
The price is ￥29,026
￥32,364 total
includes taxes & fees
May 31 - Jun 1
Arden Forest Inn
Dining

Clearview Comfort 3BR Near Airport

Clearview Comfort 3BR Near Airport
3.0 star property
23.3 km from Historic Downtown District
10.0 out of 10, Exceptional, (3 reviews)
"The house is clean. There is 1 driveway parking, however street parking is available. Location is good, there are many dining and grocery options nearby."
United States
Phuc
The price is ￥20,612
￥44,465 total
includes taxes & fees
May 28 - May 29
Clearview Comfort 3BR Near Airport
Lobby lounge

Compass by Margaritaville in Medford

Compass by Margaritaville in Medford
4.0 star property
16.3 km from Historic Downtown District
9.6 out of 10, Exceptional, (1,007 reviews)
"Breakfast was fresh and delicious, room was nice and clean, and staff super friendly "
United States
Gilbert
The price is ￥22,790
￥27,549 total
includes taxes & fees
May 31 - Jun 1
Compass by Margaritaville in Medford
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.
Mosby Creek Covered Bridge in Cottage Grove, Oregon, United States

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.

Street scene in downtown Ashland Oregon state.

Siskiyou-Hargadine Historic District

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

Aerial view of Ashland, Oregon

Skidmore Academy Historic District

Skidmore Academy Historic District might not have many top sights, but Allen Elizabethan Theatre and Angus Bowmer Theatre are two attractions nearby that you can check out.

Top Historic Downtown District Hotel Reviews

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

8/10 Good
"We really like this hotel a lot. The staff is great. Unfortunately, the hot tub has been broken the last 2 times we have been here. We were disappointed that when we checked in we were not informed about it not working, nor were we offered any type of compensation. The hot tub is one of the main reasons we like staying here. Also, since the new owners a corporation, took over, there is no longer the complimentary breakfast or the shuttle that took us into town."
jeanne 1-night trip
Posted 5 hours ago
Ashland Hills Hotel & Suites

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 Angus Bowmer Theatre as part of your Historic Downtown District travel plans.
What's the best accommodation in Historic Downtown District?
Based on our traveler data, The Bard's Inn, BW Signature Collection by Best Western is one of the top choices for your stay in Historic Downtown District. This hotel offers free breakfast and free parking. Other good options for your stay in the area include Ashland Springs Hotel and Winchester Inn.
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 28 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.