Ashland Holidays
Book a Hotel + Flight or Car together to unlock savings
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.
Top hotels in Ashland
Ashland Hills Hotel & Suites
2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
The price is 2.359.342 ₫ per night from 1 Jan to 2 Jan
2.359.342 ₫
2.925.679 ₫ total
1 Jan - 2 Jan 2026
includes taxes & fees
8.8/10 Excellent! (1,492 reviews)
A great place
Reviewed on 7 Dec 2025
Stratford Inn
555 Siskiyou Blvd Ashland OR
Fully refundable
The price is 2.369.610 ₫ per night from 14 Dec to 15 Dec
2.369.610 ₫
2.642.115 ₫ total
14 Dec - 15 Dec
includes taxes & fees
9.2/10 Wonderful! (1,596 reviews)
We had a great stay! Haven’t stayed here since 2001. Happy to report that the Stratford is in great shape and the staff is still friendly, knowledgeable, and super helpful.
Reviewed on 8 Dec 2025
Flagship Inn of Ashland
1193 Siskiyou Blvd Ashland OR
Fully refundableReserve now, pay when you stay
The price is 1.658.727 ₫ per night from 13 Dec to 14 Dec
1.658.727 ₫
1.849.612 ₫ total
13 Dec - 14 Dec
includes taxes & fees
8.6/10 Excellent! (1,183 reviews)
Our stay was fine. We had issues with our room keys as they would only open the door after several attempts even though the light was green each time we swiped the card. On our second day there they card keys didn't work at all so we had to have the front desk fix them as they shut down after 11am ...
Reviewed on 8 Dec 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.
Popular places to visit
Mount Ashland Ski Area
Hit the slopes in Ashland with a visit to Mount Ashland Ski Area. Discover the top-notch restaurants and entertainment choices in this walkable area.
Southern Oregon University
Walk around the campus at Southern Oregon University during your visit to Ashland. Experience the area's lively festivals and entertainment choices.
Lithia Park
Explore the great outdoors at Lithia Park, a lovely green space in Ashland. Discover the top-notch restaurants and acclaimed theatre scene in this family-friendly area.
