Lodging Image

Hotels in Historic Downtown District

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Filter by

Property class

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Historic Downtown District hotels

An outdoor patio area with tables and chairs, string lights, and potted plants.

1. Ashland Springs Hotel

Ashland Springs Hotel
3.0 star property
Historic Downtown District
9.2 out of 10, Wonderful, (1,008 reviews)
"Location is perfect for Ashland."
United States
Duff
The price is S$154
includes taxes & fees
17 Nov - 18 Nov
Ashland Springs Hotel
A spacious lobby with a reception desk, seating area, and large windows.

2. 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
8.4 out of 10, Very good, (1,012 reviews)
"Location is very convenient to nice walks, restaurants and shops."
United States
Thomas
The price is S$141
includes taxes & fees
26 Nov - 27 Nov
The Bard's Inn, BW Signature Collection by Best Western
A Victorian-style building with ornate architectural details, large windows, and a red door.

3. McCall House Boutique Inn

McCall House Boutique Inn
4.0 star property
Historic Downtown District
9.4 out of 10, Exceptional, (619 reviews)
"All good; would stay again. Great breakfast too"
United States
Elizabeth
The price is S$242
includes taxes & fees
1 Nov - 2 Nov
McCall House Boutique Inn
A large, two-story house with a wrap-around porch and a steeply pitched roof.

4. Winchester Inn

Winchester Inn
3.5 star property
Historic Downtown District
9.6 out of 10, Exceptional, (291 reviews)
"Amazing breakfasts, friendly staff, best location"
United States
Ellen
The price is S$211
includes taxes & fees
9 Nov - 10 Nov
Winchester Inn
An indoor swimming pool with clear water, tiled edges, and a blue mosaic border. There are lounge chairs and potted plants near the windows.

5. Stratford Inn

Stratford Inn
2.5 star property
Siskiyou-Hargadine Historic District, 0.6 km from Historic Downtown District
9.4 out of 10, Exceptional, (1,801 reviews)
"very nice inn to stay."
United States
David
The price is S$133
includes taxes & fees
1 Nov - 2 Nov
Stratford Inn
An outdoor dining area with a table set for two, surrounded by chairs, a red umbrella, and a stone water feature.

6. Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek
3.0 star property
0.4 km from Historic Downtown District
9.0 out of 10, Wonderful, (1,013 reviews)
"Very nicece hotel and perfect location for walking and exploring Ashland."
United States
Heather
The price is S$166
includes taxes & fees
9 Nov - 10 Nov
Plaza Inn & Suites at Ashland Creek
A two-story building with a wooden facade, large windows, and a front porch with chairs.

7. The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges
2.0 star property
Historic Railroad District, 0.5 km from Historic Downtown District
9.6 out of 10, Exceptional, (118 reviews)
"My room was clean, bed was comfortable. It was really nice and central to restaurants, coffee shops and downtown. It was nice having a door code instead of keys etc. would stay here again"
Canada
Lindsay
The price is S$218
includes taxes & fees
9 Nov - 10 Nov
The Peerless Hotel by WanderLodges
A balcony with a view of a residential area, a black pickup truck, and a white RV parked in the foreground.

8. Ashland Commons Hostel

Ashland Commons Hostel
2.0 star property
0.8 km from Historic Downtown District
9.4 out of 10, Exceptional, (75 reviews)
"Great place to stay. Excellent location."
United States
Sam
The price is S$95
includes taxes & fees
9 Nov - 10 Nov
Ashland Commons Hostel
A resort with a covered walkway, potted plants, and a statue.

9. Lithia Springs Resort

Lithia Springs Resort
3.0 star property
3.6 km from Historic Downtown District
9.4 out of 10, Exceptional, (1,007 reviews)
"Very well kept rooms, beautiful grounds and whole resort has a quiet calming quality."
United States
Steven
The price is S$147
includes taxes & fees
16 Nov - 17 Nov
Lithia Springs Resort
A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

10. Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
1.1 km from Historic Downtown District
10.0 out of 10, Exceptional, (10 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is S$326
includes taxes & fees
29 Oct - 30 Oct
Barclay Klum House by WanderLodges
A sign for Prospero's Flagship Inn with a star emblem and a pedestrian crossing sign nearby.

11. Prospero's Flagship Inn

Prospero's Flagship Inn
2.5 star property
1.9 km from Historic Downtown District
8.4 out of 10, Very good, (1,490 reviews)
"We enjoyed our stay very much. The location was good; the staff great and our room was very nice"
United States
Mary
The price is S$94
includes taxes & fees
31 Oct - 1 Nov
Prospero's Flagship Inn
A Holiday Inn Express hotel with a two-story structure, a parking lot, and a landscaped area with shrubs and a tall tree.

12. 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
9.4 out of 10, Exceptional, (1,009 reviews)
"Great option not too far from downtown Ashland. Clean and new, decent breakfast, oool and hot tub"
United States
Lorenzo
The price is S$146
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Express & Suites Ashland by IHG
A swimming pool with a clear view of the poolside area, including lounge chairs and a covered seating area.

13. Timbers INN and Suites

Timbers INN and Suites
2.0 star property
2.3 km from Historic Downtown District
8.8 out of 10, Excellent, (1,006 reviews)
"Our room was very clean and comfortable and our staff interaction was great. We’ll definitely stay here again when we come to Ashland."
United States
Sarah
The price is S$98
includes taxes & fees
6 Nov - 7 Nov
Timbers INN and Suites
A garden pathway with wisteria and red flowers, surrounded by lush greenery.

14. Arden Forest Inn

Arden Forest Inn
4.0 star property
0.8 km from Historic Downtown District
9.8 out of 10, Exceptional, (115 reviews)
"Terrific in all aspects. Look forward to returning."
United States
Thomas
The price is S$244
includes taxes & fees
18 Nov - 19 Nov
Arden Forest Inn
A spacious lobby with a large wooden floor, a green peace sign decoration, and a large window offering a view of the outdoors.

15. 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, (1,572 reviews)
"Clean rooms, nice location."
United States
Nicholas
The price is S$153
includes taxes & fees
16 Nov - 17 Nov
Ashland Hills Hotel & Suites
A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

16. Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District, 0.4 km from Historic Downtown District
10.0 out of 10, Exceptional, (6 reviews)
"Very cute cottage, 10 min walk to OSF theaters. It has everything you need - full kitchen, front room, and AC for the hot summers! Owner very kind. Will stay there again!"
United States
Robert
The price is S$259
includes taxes & fees
10 Nov - 11 Nov
Hanna's House by WanderLodges
A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

17. Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District, 0.8 km from Historic Downtown District
10.0 out of 10, Exceptional, (2 reviews)
"Had an amazing stay, thank you!"
United States
megan
The price is S$441
includes taxes & fees
22 Nov - 23 Nov
Savage Upon Siskiyou
A hotel entrance with outdoor seating, potted plants, and a well-lit facade.

18. Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland
2.5 star property
3.9 km from Historic Downtown District
9.0 out of 10, Wonderful, (1,059 reviews)
"Clean rooms, good breakfast, conveniently located."
United States
Bill
The price is S$136
includes taxes & fees
15 Nov - 16 Nov
Comfort Inn & Suites Ashland
Exterior

19. 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, (1,006 reviews)
"Great location, clean room, friendly staff"
United States
Ross
The price is S$161
includes taxes & fees
6 Nov - 7 Nov
Best Western Windsor Inn
A swimming pool with lounge chairs and umbrellas, surrounded by trees and a covered seating area.

20. Palm Cottages

Palm Cottages
2.5 star property
1.6 km from Historic Downtown District
9.2 out of 10, Wonderful, (233 reviews)
"Palm Cottages is a clean and wonderful boutique hotel on the outskirts of downtown Ashland. We only stayed one night but we will definitely be back again some day. Thank you 🙏"
United States
Eric
The price is S$287
includes taxes & fees
29 Oct - 30 Oct
Palm Cottages
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.
View all properties

Compare top hotels in Historic Downtown District

An outdoor patio area with tables and chairs, string lights, and potted plants.

Ashland Springs Hotel

3.0 star property
Historic Downtown District
View
A spacious lobby with a reception desk, seating area, and large windows.

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

2.5 star property
Historic Downtown District
View
A Victorian-style building with ornate architectural details, large windows, and a red door.

McCall House Boutique Inn

4.0 star property
Historic Downtown District
View
A large, two-story house with a wrap-around porch and a steeply pitched roof.

Winchester Inn

3.5 star property
Historic Downtown District
View
An indoor swimming pool with clear water, tiled edges, and a blue mosaic border. There are lounge chairs and potted plants near the windows.

Stratford Inn

2.5 star property
Siskiyou-Hargadine Historic District, 0.6 km from Historic Downtown District
View
9.2
Wonderful
1,008 reviews
8.4
Very good
1,012 reviews
9.4
Exceptional
619 reviews
9.6
Exceptional
291 reviews
9.4
Exceptional
1,801 reviews
The price is S$154
includes taxes & fees
17 Nov - 18 Nov
The price is S$141
includes taxes & fees
26 Nov - 27 Nov
The price is S$242
includes taxes & fees
1 Nov - 2 Nov
The price is S$211
includes taxes & fees
9 Nov - 10 Nov
The price is S$133
includes taxes & fees
1 Nov - 2 Nov
  • No Breakfast included
  • No Pool
  • Yes, Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • No Pool
  • No Spa
  • No Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • No Pool
  • No Spa
  • No Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • Yes, Parking

Where to stay in Historic Downtown District

Find the best Historic Downtown District areas for the activities you enjoy most.
A rusted metal bridge in a forested area.

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.

A tree-lined street with a mountain backdrop.

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.

A town with buildings and trees in autumn colors, surrounded by mountains.

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

Executive Residency by Best Western Medford

Executive Residency by Best Western Medford

10/10 Excellent
"Overall it is nice and clean. Staff is ok, not too friendly. But polite. Great location. Will consider again next time driving by."
Charlotte 1-night trip
Posted 5 hours ago
Executive Residency by Best Western Medford

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 our traveller 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 26 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.

Explore a world of travel with Expedia