Search for Cheap Deals on
Hotels in Ashland

Choose from 785 Ashland Hotel Deals

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
  • 21 min walk from Oregon Shakespeare Festival
Book a stay at this business-friendly hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,474 reviews)
Clean room | Great Location | Visiting 4th time

Reviewed on May 11, 2026

Ashland Hills Hotel & Suites
Prospero's Flagship Inn

Prospero's Flagship Inn

2.5 out of 5
1193 Siskiyou Blvd Ashland OR
  • 14 min walk from Oregon Shakespeare Festival
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,307 reviews)
Booked this motel specifically because there was an outdoor pool and the weather was predicted to be super warm. Apparently, May is still winter months. When we arrived the pool was green and still closed. I accept that I did not call in advance but May is closer to Summer than Winter. To make matters ...

Reviewed on May 11, 2026

Prospero's Flagship Inn
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
  • 4 min walk from Oregon Shakespeare Festival
Stay at this hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular ...
9.4/10 Exceptional! (1,769 reviews)
Clean and quiet room and friendly staff. Easily walkable to downtown Ashland and OSF theaters. Breakfast was passable but not great.

Reviewed on May 11, 2026

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

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

2.5 out of 5
132 N Main Street Ashland OR
  • 5 min walk from Oregon Shakespeare Festival
Stay at this hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (1,013 reviews)
Excellent staff. The hotel is located right next to downtown Asland with access to restaurants, theater, and Lithia Park. They have a slow charger for electric vehicles. The chairs are cushioned and low to the ground and you sink, making the table come up to your chest so you can't get any work done ...

Reviewed on May 12, 2026

The Bard's Inn, BW Signature Collection by Best Western
Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek

3 out of 5
98 Central Ave Ashland OR
  • 6 min walk from Oregon Shakespeare Festival
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.8/10 Excellent! (1,011 reviews)
Clean, spacious room. Close to restaurants and shops. Friendly staff. Good breakfast.

Reviewed on May 10, 2026

Plaza Inn & Suites at Ashland Creek
Lithia Springs Resort

Lithia Springs Resort

3 out of 5
2165 W Jackson Rd Ashland OR
  • 4 min drive from Oregon Shakespeare Festival
Stay at this B&B in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. ...
9.4/10 Exceptional! (1,012 reviews)
The breakfast is great - fresh fruit and a selection of hot food. The site is very nice, the rooms are quite clean and the staff is helpful.

Reviewed on May 11, 2026

Lithia Springs Resort
Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
  • 1 min walk from Oregon Shakespeare Festival
Book a stay at this spa hotel in Ashland. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the breakfast and the helpful staff in our ...
9.2/10 Wonderful! (1,011 reviews)
Everything was good. We were missing more information about the options for breakfast, tea or dinner.

Reviewed on May 11, 2026

Ashland Springs Hotel
Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

2.5 out of 5
434 S. Valley View Rd. Ashland OR
  • 5 min drive from Oregon Shakespeare Festival
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.8/10 Excellent! (1,009 reviews)
Well maintained & clean. Great amenities.

Reviewed on May 8, 2026

Comfort Inn & Suites Ashland
Best Western Windsor Inn

Best Western Windsor Inn

2.5 out of 5
2520 Ashland St Ashland OR
  • 21 min walk from Oregon Shakespeare Festival
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,006 reviews)
We had a wonderful stay at this hotel. The room was clean, comfortable, and well maintained, and the staff was friendly and welcoming throughout our visit. The overall atmosphere was relaxing, and our family truly enjoyed our time here. We would definitely stay again and highly recommend this hotel ...

Reviewed on May 9, 2026

Best Western Windsor Inn
Callahan's Mountain Lodge

Callahan's Mountain Lodge

3 out of 5
7100 Old Highway 99 South Ashland OR
  • 21 min drive from Oregon Shakespeare Festival
Book a stay at this family-friendly lodge in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in ...
8.8/10 Excellent! (1,175 reviews)
We stayed three nights in one of the rooms with the spa tub. It worked well. The bed was comfortable. The only part that was a little bit of a disappointment was the continental breakfast. But otherwise it was a nice place to stay. We would come back again.

Reviewed on May 12, 2026

Callahan's Mountain Lodge
Timbers INN and Suites

Timbers INN and Suites

2 out of 5
1450 Ashland Street Ashland OR
  • 16 min walk from Oregon Shakespeare Festival
Stay at this motel in Ashland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8.6/10 Excellent! (1,005 reviews)
Nice tv. Not enough towels. Shower head worn out, leaked, it got the floor very wet. Toilet didn't flush right , worn out! Bathtub needed resurfacing. Looked horrible

Reviewed on May 4, 2026

Timbers INN and Suites
Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG

2.5 out of 5
565 Clover Lane Ashland OR
  • 22 min walk from Oregon Shakespeare Festival
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,007 reviews)
Have stayed here many times! Always been top notch. Clean. Great service. Highly recommended.

Reviewed on May 11, 2026

Holiday Inn Express & Suites Ashland by IHG
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.

Find cheap hotels in Ashland

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Ashland hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Ashland.

Choosing the right hotel in Oregon has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Ashland’s 785 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $72. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Ashland hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Ashland. No matter your reason for visiting Ashland, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Ashland hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Ashland for as low as $72.

How many hotels are there in Ashland?

With over 785 hotels in Ashland, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $72.

How to find cheap car rentals in Ashland?

Finding a cheap car rental deal in Ashland is as easy as scoring cheap hotels in Ashland. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.