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Historic Downtown District Hotels, Ashland

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Our top choices for Historic Downtown District hotels

1. Ashland Springs Hotel

Ashland Springs Hotel
3.0 star property
Historic Downtown District
9.2 out of 10, Wonderful, (1,011 reviews)
"Cutest hotel ever! Will stay again."
Canada
Tamara
The price is NZ$216
includes taxes & fees
1 Dec - 2 Dec
Ashland Springs Hotel

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, (1,004 reviews)
"Love this place"
United States
Jess
The price is NZ$191
includes taxes & fees
24 Nov - 25 Nov
The Bard's Inn, BW Signature Collection by Best Western

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 NZ$290
includes taxes & fees
9 Nov - 10 Nov
Winchester Inn

4. McCall House Boutique Inn

McCall House Boutique Inn
4.0 star property
Historic Downtown District
9.6 out of 10, Exceptional, (620 reviews)
"All good; would stay again. Great breakfast too"
United States
Elizabeth
The price is NZ$317
includes taxes & fees
9 Nov - 10 Nov
McCall House Boutique Inn

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, (1,799 reviews)
"Nice little hotel that was well decorated for the holiday."
United States
Thomas
The price is NZ$188
includes taxes & fees
10 Nov - 11 Nov
Stratford Inn

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, (1,007 reviews)
"Very nicece hotel and perfect location for walking and exploring Ashland."
United States
Heather
The price is NZ$234
includes taxes & fees
9 Nov - 10 Nov
Plaza Inn & Suites at Ashland Creek

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, (119 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 NZ$271
includes taxes & fees
22 Nov - 23 Nov
The Peerless Hotel by WanderLodges

8. Ashland Commons Hostel

Ashland Commons Hostel
2.0 star property
0.8 km from Historic Downtown District
9.4 out of 10, Exceptional, (76 reviews)
"Great place to stay. Excellent location."
United States
Sam
The price is NZ$136
includes taxes & fees
15 Nov - 16 Nov
Ashland Commons Hostel

9. 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, (1,491 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 NZ$134
includes taxes & fees
9 Nov - 10 Nov
Prospero's Flagship Inn

10. 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)
"Tasteful charming bedroom and bathroom."
United States
Jean
The price is NZ$275
includes taxes & fees
9 Nov - 10 Nov
Arden Forest Inn

11. Lithia Springs Resort

Lithia Springs Resort
3.0 star property
3.6 km from Historic Downtown District
9.4 out of 10, Exceptional, (1,010 reviews)
"Well maintained, affordable delicious breakfast, clean rooms"
United States
Christina
The price is NZ$207
includes taxes & fees
16 Nov - 17 Nov
Lithia Springs Resort

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, (1,006 reviews)
"Very friendly staff."
Canada
Tanis
The price is NZ$185
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express & Suites Ashland by IHG

13. Whimsy On B 2br & Studio

Whimsy On B 2br & Studio
2.5 star property
Historic Railroad District, 0.2 km from Historic Downtown District
The price is NZ$576
includes taxes & fees
15 Nov - 16 Nov
Whimsy On B 2br & Studio

14. 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 NZ$459
includes taxes & fees
6 Dec - 7 Dec
Barclay Klum House by WanderLodges

15. 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, (1,004 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 NZ$145
includes taxes & fees
9 Nov - 10 Nov
Timbers INN and Suites

16. 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 NZ$382
includes taxes & fees
9 Nov - 10 Nov
Abigail’s Bed & Breakfast Inn

17. 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, (1,578 reviews)
"Great hotel!"
United States
Nicholas
The price is NZ$215
includes taxes & fees
9 Nov - 10 Nov
Ashland Hills Hotel & Suites

18. 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 NZ$323
includes taxes & fees
10 Nov - 11 Nov
Hanna's House by WanderLodges

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, (1,001 reviews)
"Great location, clean room, friendly staff"
United States
Ross
The price is NZ$226
includes taxes & fees
15 Nov - 16 Nov
Best Western Windsor Inn

20. 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 NZ$636
includes taxes & fees
10 Nov - 11 Nov
Savage Upon Siskiyou
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.

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
A Victorian-style building with ornate architectural details, large windows, and a red door.
McCall House Boutique Inn
4.0 star property
9.6
Exceptional
620 reviews
View
A grand lobby with a high ceiling, large windows, and a central staircase.
Ashland Springs Hotel
3.0 star property
9.2
Wonderful
1,011 reviews
View
A hotel with a brick-paved courtyard, a stone wall, and a two-story building with a balcony.
The Bard's Inn, BW Signature Collection by Best Western
2.5 star property
8.4
Very good
1,004 reviews
View
A two-story building with a wooden facade, large windows, and a front porch with chairs.
The Peerless Hotel by WanderLodges
2.0 star property
9.6
Exceptional
119 reviews
View

Our guide on where to stay in Historic Downtown District

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

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.

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.

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

Recent Reviews in Historic Downtown District

Frequently asked questions

What are the best hotels in Historic Downtown District that travellers recommend?
Two of the best hotels in Historic Downtown District that receive consistently high recommendations from travellers are the McCall House Boutique Inn and the Winchester Inn.

The McCall House Boutique Inn, with an outstanding 9.6 rating, offers a luxurious experience with amenities such as designer toiletries, rainfall showerheads, and deep soaking bathtubs. Guests frequently highlight the lovely breakfast, wonderful service, and beautiful house. It is conveniently located just 0.2 km from the Oregon Shakespeare Festival, the Allen Elizabethan Theatre, and the Angus Bowmer Theatre.

Another highly recommended option is the Winchester Inn, which also has an impressive 9.6 rating. This hotel provides premium bedding, Egyptian cotton sheets, and deep soaking bathtubs. Visitors often praise its clean and great rooms, fabulous staff, and wonderful breakfast. It is situated 0.3 km from the Oregon Shakespeare Festival and the Allen Elizabethan Theatre, and 0.2 km from Ashland Library.
What are the best family hotels in Historic Downtown District?
When searching for the best family hotels in Historic Downtown District, consider the Ashland Springs Hotel, The Bard's Inn, BW Signature Collection by Best Western, Winchester Inn, and McCall House Boutique Inn.

The Ashland Springs Hotel, with a 9.2 rating, is a great choice for families. It provides sofa beds for extra sleeping space and is part of Historic Hotels of America, offering a unique stay. Its location is convenient for various activities, being just 1.9 km from ScienceWorks Hands-On Museum and 0.2 km from the Oregon Shakespeare Festival. Guests often praise its comfortable and clean rooms, helpful staff, and delicious free breakfast.

The Bard's Inn, BW Signature Collection by Best Western, rated 8.6, also caters well to families. It offers sofa beds, free rollaway extra beds, and connecting rooms, providing flexibility for larger groups. You can enjoy a complimentary breakfast, including a convenient to-go option. The hotel is situated 0.4 km from the Oregon Shakespeare Festival and 1.1 km from Lithia Park. Guests consistently mention the comfortable rooms and good continental breakfast.

For another excellent family option, the Winchester Inn, with an outstanding 9.6 rating, is highly recommended. It features free rollaway extra beds, sofa beds, and complimentary cooked breakfast, along with free toiletries and free WiFi. Self-parking is also free. This inn is very close to the Oregon Shakespeare Festival, just 0.3 km away, and 0.2 km from Ashland Library. Reviews frequently highlight the clean rooms, fabulous staff, and wonderful breakfast.

Finally, the McCall House Boutique Inn, rated 9.6, is an ideal choice for families. It provides sofa beds and child-friendly window designs for added safety. The inn is conveniently located 0.2 km from the Oregon Shakespeare Festival and Allen Elizabethan Theatre. Guests consistently praise the lovely and delicious breakfast, attentive service, and beautiful house.
What are the best spa hotels in Historic Downtown District?
For a spa hotel in the Historic Downtown District, the Ashland Springs Hotel is an excellent choice.

The Ashland Springs Hotel, with a 9.2 rating, offers a full-service spa where guests can indulge in a variety of treatments. These include hydrotherapy, aromatherapy, body wraps, body scrubs, and facials. The spa also features a hot tub, sauna, and dedicated treatment rooms, including options for couples' treatments and Ayurvedic therapies. Guests consistently praise its great location and comfortable, clean rooms.

This hotel provides an extensive spa experience for a relaxing stay.
What hotels in Historic Downtown District offer free breakfast?
For hotels in Historic Downtown District offering complimentary breakfast, consider the McCall House Boutique Inn, the Winchester Inn, and The Bard's Inn, BW Signature Collection by Best Western.

The McCall House Boutique Inn, with an outstanding 9.6 rating, offers a lovely and delicious full breakfast, which guests consistently praise. The staff are described as attentive and wonderful, and the beautiful house itself is a popular feature. It is also conveniently located just 0.2 km from the Oregon Shakespeare Festival.

Another excellent choice is the Winchester Inn, also boasting a 9.6 rating. This inn provides a wonderful and amazing cooked breakfast, which is a highlight for many guests. The rooms are clean and great, and the staff are noted as helpful and fabulous. The inn is situated close to the Oregon Shakespeare Festival, only 0.3 km away.

The Bard's Inn, BW Signature Collection by Best Western, rated 8.6, also offers a complimentary breakfast, including a convenient to-go option. Guests appreciate the good location and comfortable rooms, with many finding the continental breakfast to be above average. It's a short 0.4 km walk to the Oregon Shakespeare Festival.
What are the top pet-friendly hotels in Historic Downtown District?
For top pet-friendly hotels in the Historic Downtown District, consider The Bard's Inn, BW Signature Collection by Best Western and the Ashland Springs Hotel.

The Bard's Inn, BW Signature Collection by Best Western, with an 8.6 rating, welcomes both dogs and cats. Guests frequently praise its great location and comfortable rooms. Mountain biking and mountain climbing are available nearby for active pets and owners, and some rooms offer mountain views. It is conveniently located near the Oregon Shakespeare Festival, Allen Elizabethan Theatre, and Angus Bowmer Theatre, all within 0.4 km, and Lithia Park is just 1.1 km away.

Another excellent option is the Ashland Springs Hotel, boasting an impressive 9.2 rating. This hotel is also pet-friendly and is situated in a historical district. It is highly rated for its great location, comfortable and clean rooms, and helpful staff. The hotel offers an on-site spa with various treatments including hydrotherapy, aromatherapy, and massage, as well as a hot tub and sauna. It is exceptionally close to the Oregon Shakespeare Festival (0.2 km), Ashland Library (0.3 km), Allen Elizabethan Theatre (0.1 km), and Angus Bowmer Theatre (0.1 km).
What are the top boutique hotels in Historic Downtown District?
For a top boutique hotel in the Historic Downtown District, the Ashland Springs Hotel is an excellent choice.

This hotel, with an impressive 9.2 rating, is a Beaux Arts property that is part of Historic Hotels of America. Guests consistently praise its great location, comfortable and clean rooms, and the helpful and attentive staff. A delicious complimentary breakfast is also frequently mentioned. The hotel features a full-service spa with hydrotherapy treatments, a hot tub, a sauna, and various body and facial treatments, including couples treatment rooms. It is also conveniently located just 0.1 km from the Allen Elizabethan Theatre.
What are the best budget hotels in Historic Downtown District?
For excellent budget-friendly hotels in the Historic Downtown District, consider The Bard's Inn, BW Signature Collection by Best Western and the Ashland Springs Hotel.

The Bard's Inn, BW Signature Collection by Best Western, rated 8.6, offers complimentary breakfast, free toiletries, and free self-parking, along with free WiFi. Guests appreciate the comfortable rooms and above-average continental breakfast, and its location is great, just 0.4 km from the Oregon Shakespeare Festival.

Another highly-rated option is the Ashland Springs Hotel, with an impressive 9.2 rating. This hotel provides free WiFi, free toiletries, and free self-parking. It is known for its historic charm and is situated in a nice historical district, only 0.2 km from the Oregon Shakespeare Festival and 0.8 km from Lithia Park. Guests consistently praise the comfortable, clean rooms and the helpful, attentive staff.
What are the most romantic hotels in Historic Downtown District for couples?
For a romantic getaway in Historic Downtown District, consider the McCall House Boutique Inn or the Winchester Inn.

The McCall House Boutique Inn, with an outstanding rating of 9.6, is highly regarded by guests for its beautiful house and lovely, delicious breakfast. The attentive and wonderful service from the staff is frequently highlighted. It is also conveniently located just 0.2 km from the Allen Elizabethan Theatre.

Another excellent choice for couples is the Winchester Inn, which also boasts a 9.6 rating. Guests consistently praise its clean, great rooms and helpful, fabulous staff. The wonderful and amazing breakfast, along with the fabulous on-site restaurant, are also highly recommended. Many rooms offer a balcony or furnished balcony, great for enjoying some quiet time together. It is located 0.3 km from the Allen Elizabethan Theatre.
What are the best hotels in Historic Downtown District near Lithia Park?
For hotels in the Historic Downtown District near Lithia Park, consider the McCall House Boutique Inn or the Winchester Inn.

The McCall House Boutique Inn, with an exceptional rating of 9.6, is conveniently located just 1.0 km from Lithia Park. Guests frequently praise the lovely and delicious breakfast, the attentive and wonderful service, and the beautiful house itself. Its proximity to the Oregon Shakespeare Festival and the Allen Elizabethan Theatre (both 0.2 km away) makes it ideal for theatre-goers.

Another excellent option is the Winchester Inn, also boasting an impressive 9.6 rating. While slightly further from Lithia Park, its location is still very convenient for exploring the Historic Downtown District. Guests consistently highlight the clean and great rooms, the helpful and fabulous staff, and the wonderful and amazing breakfast, which is complimentary. The inn also offers free WiFi and free self-parking.
When is the best time to go to Historic Downtown District?
The best time to visit the Historic Downtown District is during the late spring (May to early June) and early autumn (September to October) when the weather is pleasant and the crowds are smaller.

During these shoulder seasons, you'll find comfortable temperatures great for exploring the district's outdoor attractions and walking tours without the peak summer heat or the larger crowds. The foliage in autumn also adds a beautiful backdrop to the historic architecture, and spring brings blooming flowers.

For those who enjoy outdoor activities like hiking and cycling in the surrounding areas, these months offer ideal conditions. Many of the local shops and restaurants are also less busy, allowing for a more relaxed and personal experience.

While summer (July and August) is also a popular time, it can be quite busy with tourists, and accommodation prices may be higher.
Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline − this is often within 24 to 48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our 'Fully refundable property' filter during your search to find the right Historic Downtown District hotel for you.
How can I save on a hotel booking in Historic Downtown District with Expedia?
One Key™—Expedia's free travel rewards programme—gives you instant access to discounts with Member Prices on Historic Downtown District hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Historic Downtown District?
Hotel prices in Historic Downtown District often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates and sort search results by 'Price: low to high' for our cheapest rates.