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 Thomas Theatre and Oregon Shakespeare Festival.
Ashland Holiday
Our pick of the best Ashland Hotel Deals
Ashland Hills Hotel & Suites
2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
The price is NZ$192 per night from 1 Jan to 2 Jan
NZ$192
1 Jan - 2 Jan 2026
includes taxes & fees
8.8/10 Excellent! (1,482 reviews)
I love staying here because the decoration is so great and the food and service is phenomenal.
Reviewed on 1 Dec 2025
Stratford Inn
555 Siskiyou Blvd Ashland OR
Fully refundable
The price is NZ$174 per night from 8 Dec to 9 Dec
NZ$174
8 Dec - 9 Dec
includes taxes & fees
9.2/10 Wonderful! (1,589 reviews)
My daughter recommended Stratford Inn and I'm glad I took her advice. The desk clerk was helpful as well as professional. My room was on the 2nd floor, and he offered a cart, similar to those at airports, to more easily move my belongings upstairs via the elevator. My bed was comfortable and the ...
Reviewed on 3 Dec 2025
Flagship Inn of Ashland
1193 Siskiyou Blvd Ashland OR
Fully refundableReserve now, pay when you stay
The price is NZ$117 per night from 13 Dec to 14 Dec
NZ$117
13 Dec - 14 Dec
includes taxes & fees
8.6/10 Excellent! (1,184 reviews)
Staff was fabulous (Crystal), and the room is great. Thank you!
Reviewed on 30 Nov 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.
