Ashland Holidays
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Our guide on where to stay in Ashland
Find the best Ashland areas and neighborhoods for the activities you enjoy most. Learn more about Ashland
Historic Downtown District
4 out of top 10 points of interest in this area
While visiting Historic Downtown District, you might make a stop by sights like Allen Elizabethan Theatre and Oregon Shakespeare Festival.
Ashland Holiday
Our pick of the best Ashland Hotel Deals
Flagship Inn of Ashland
1193 Siskiyou Blvd, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is NZ$149 per night from 26 Oct to 27 Oct
NZ$149
26 Oct - 27 Oct
includes taxes & fees
8.6/10 Excellent! (1,104 reviews)
"Easy check-in and check out, room was clean and comfortable, and breakfast was surprisingly good for such a small property."
Reviewed on 17 Oct 2025
Ashland Hills Hotel & Suites
2525 Ashland St, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is NZ$235 per night from 26 Oct to 27 Oct
NZ$235
26 Oct - 27 Oct
includes taxes & fees
8.8/10 Excellent! (1,494 reviews)
"The front desk staff was exceptionally nice. Parking lot and self parking great. Property was clean. This is definitely a VINTAGE hotel. Design from the 1968-1975 timeframe. I believe rather than remodel things, they designed the hotel around this 1970s vintage theme. For example our bathroom had ..."
Reviewed on 18 Oct 2025
Stratford Inn
555 Siskiyou Blvd, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is NZ$210 per night from 4 Nov to 5 Nov
NZ$210
4 Nov - 5 Nov
includes taxes & fees
9.2/10 Wonderful! (1,582 reviews)
"Lovely, comfortable room. Great location for walking tp/frim the theaters."
Reviewed on 19 Oct 2025
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.
Discover the most popular places to visit in Ashland
Oregon Cabaret Theatre
You can get tickets for a performance at Oregon Cabaret Theatre during your stay in Ashland. Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants.
Allen Elizabethan Theatre
You can enjoy a show at Allen Elizabethan Theatre during your trip to Ashland. Wander around the area's picturesque gardens or experience its entertainment choices.
What to do in Ashland
More holiday ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
