Lodging Image

Hotels in Historic Downtown District, Ashland

  • 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
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Filter by

Star rating

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, (1,004 reviews)
"Location is perfect for Ashland."
United States
Duff
The price is RM347
RM450 total
includes taxes & fees
19 Nov - 20 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, (1,009 reviews)
"Location is very convenient to nice walks, restaurants and shops."
United States
Thomas
The price is RM469
RM523 total
includes taxes & fees
19 Nov - 20 Nov
The Bard's Inn, BW Signature Collection by Best Western
A large, two-story house with a wrap-around porch and a steeply pitched roof.

3. 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 RM545
RM673 total
includes taxes & fees
9 Nov - 10 Nov
Winchester Inn
A Victorian-style building with ornate architectural details, large windows, and a red door.

4. McCall House Boutique Inn

McCall House Boutique Inn
4.0 star property
Historic Downtown District
9.2 out of 10, Wonderful, (618 reviews)
"All good; would stay again. Great breakfast too"
United States
Elizabeth
The price is RM639
RM713 total
includes taxes & fees
1 Nov - 2 Nov
McCall House Boutique 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, (1,796 reviews)
"very nice inn to stay."
United States
David
The price is RM381
RM425 total
includes taxes & fees
10 Nov - 11 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, (1,003 reviews)
"Nice property, good breakfast, clean rooms, beautiful location"
United States
Bill
The price is RM474
RM528 total
includes taxes & fees
1 Nov - 2 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, (116 reviews)
"What a beautiful hotel! The interior decor is so lovely. Anyone who enjoys historic buildings will love staying here. Not only is the hotel so comfortable and relaxing, but the surrounding neighborhood is quaint and quiet, and it is a very short and easy walk to the center of town."
United States
Jaye
The price is RM423
RM695 total
includes taxes & fees
22 Nov - 23 Nov
The Peerless Hotel by WanderLodges
A swimming pool with lounge chairs and umbrellas, surrounded by trees and a covered seating area.

8. 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 RM820
RM915 total
includes taxes & fees
23 Oct - 24 Oct
Palm Cottages
A balcony with a view of a residential area, a black pickup truck, and a white RV parked in the foreground.

9. 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 RM290
RM324 total
includes taxes & fees
25 Oct - 26 Oct
Ashland Commons Hostel
A hotel room with two beds, a desk, a chair, and a window with curtains.

10. 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 RM301
RM336 total
includes taxes & fees
1 Nov - 2 Nov
Prospero's Flagship Inn
A resort with a covered walkway, potted plants, and a statue.

11. Lithia Springs Resort

Lithia Springs Resort
3.0 star property
3.6 km from Historic Downtown District
9.4 out of 10, Exceptional, (1,003 reviews)
"Very well kept rooms, beautiful grounds and whole resort has a quiet calming quality."
United States
Steven
The price is RM382
RM469 total
includes taxes & fees
16 Nov - 17 Nov
Lithia Springs Resort
A modern hotel room with a dark wood wardrobe, a black refrigerator, a microwave, a sink, and a chair.

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
9.2 out of 10, Wonderful, (1,004 reviews)
"Great option not too far from downtown Ashland. Clean and new, decent breakfast, oool and hot tub"
United States
Lorenzo
The price is RM392
RM437 total
includes taxes & fees
19 Nov - 20 Nov
Holiday Inn Express & Suites Ashland by IHG
A two-story house with a porch, surrounded by a well-maintained garden with various flowers and shrubs.

13. 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, (66 reviews)
"I have stayed in many bed and breakfasts over the years and this one ranks a perfect 10! Very clean,very friendly hosts, the absolute best breakfast of any B & B I've been to. If I'm going through Ashland in the future, this is my go to lodging. This felt like home! Hosts also were extremely helpful and knowledgeable about local dining. "
United States
Kim
The price is RM1,061
RM1,184 total
includes taxes & fees
27 Oct - 28 Oct
Abigail’s Bed & Breakfast Inn
A garden with a red pergola, a stone fountain, and purple flowers.

14. Arden Forest Inn

Arden Forest Inn
4.0 star property
0.8 km from Historic Downtown District
9.8 out of 10, Exceptional, (113 reviews)
"Tasteful charming bedroom and bathroom."
United States
Jean
The price is RM558
RM623 total
includes taxes & fees
2 Nov - 3 Nov
Arden Forest Inn
A hotel entrance with outdoor seating, potted plants, and a well-lit facade.

15. 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, (1,056 reviews)
"Clean rooms, good breakfast, conveniently located."
United States
Bill
The price is RM458
RM465 total
includes taxes & fees
22 Nov - 23 Nov
Comfort Inn & Suites Ashland
A swimming pool with a clear view of the poolside area, including lounge chairs and a covered seating area.

16. 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, (1,005 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 RM279
RM311 total
includes taxes & fees
28 Oct - 29 Oct
Timbers INN and Suites
Exterior

17. 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, (1,000 reviews)
"Room and property was clean, staff friendly and helpful, breakfast was good."
United States
Deborah
The price is RM434
RM484 total
includes taxes & fees
31 Oct - 1 Nov
Best Western Windsor Inn
A spacious lobby with a large wooden floor, a green peace sign decoration, and a large window offering a view of the outdoors.

18. 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, (1,562 reviews)
"Clean rooms, nice location."
United States
Nicholas
The price is RM403
RM490 total
includes taxes & fees
15 Nov - 16 Nov
Ashland Hills Hotel & Suites
A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

19. 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 RM481
RM1,060 total
includes taxes & fees
25 Oct - 26 Oct
Barclay Klum House by WanderLodges
A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

20. 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, (5 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 RM503
RM875 total
includes taxes & fees
2 Nov - 3 Nov
Hanna's House by WanderLodges
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 popular hotels in Historic Downtown District

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A large, two-story house with a wrap-around porch and a steeply pitched roof.
Winchester Inn
3.5 star property
9.6
Exceptional
291 reviews
View
An outdoor patio area with tables and chairs, string lights, and potted plants.
Ashland Springs Hotel
3.0 star property
9.2
Wonderful
1,004 reviews
View
A Victorian-style building with ornate architectural details, large windows, and a red door.
McCall House Boutique Inn
4.0 star property
9.2
Wonderful
618 reviews
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
8.4
Very good
1,009 reviews
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
9.4
Exceptional
1,796 reviews
View

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

Ramada by Wyndham Medford Airport North

Ramada by Wyndham Medford Airport North

10/10 Excellent
"Great staff and registration was easy."
Jacson 1-night trip
Posted 7 hours ago
Ramada by Wyndham Medford Airport North

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