Ashland Holidays
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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
5 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 Angus Bowmer Theatre.
Top hotels in Ashland
Prospero's Flagship Inn
1193 Siskiyou Blvd Ashland OR
Fully refundableReserve now, pay when you stay
The price is 2.677.049 ₫ per night from 29 Jun to 30 Jun
2.677.049 ₫
2.985.028 ₫ total
29 Jun - 30 Jun
includes taxes & fees
8.6/10 Excellent! (1,375 reviews)
"Second time here and always perfect; location near breakfast places makes it so easy to stay, or you can grab something in the breakfast room"
Reviewed on 24 Jun 2026
Ashland Hills Hotel & Suites
2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
The price is 3.529.914 ₫ per night from 12 Jul to 13 Jul
3.529.914 ₫
4.199.045 ₫ total
12 Jul - 13 Jul
includes taxes & fees
8.8/10 Excellent! (1,486 reviews)
"My room, and the whole building as I later noticed, smelled moldy/mildewy/musky."
Reviewed on 24 Jun 2026
Stratford Inn
555 Siskiyou Blvd Ashland OR
The price is 3.748.395 ₫ per night from 30 Jun to 1 Jul
3.748.395 ₫
4.179.460 ₫ total
30 Jun - 1 Jul
includes taxes & fees
9.4/10 Exceptional! (1,754 reviews)
"Nice location, but it’s a real old hotel and the pictures look much better than in real life. Breakfast was sub-par, but the staff were very nice people."
Reviewed on 21 Jun 2026
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
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.
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.
