Ashland Packages (Flight + Hotel)
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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
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 Angus Bowmer Theatre.
Top hotels in Ashland
Ashland Hills Hotel & Suites
2525 Ashland St Ashland OR
The price is ฿3,479 per night from 7 May to 8 May
฿3,479
฿4,204 total
7 May - 8 May
includes taxes & fees
8.8/10 Excellent! (1,466 reviews)
Very clean rooms; very helpful staff. Restaurant food for breakfast and dinner was excellent. Would stay here again.
Reviewed on 3 May 2026
Stratford Inn
555 Siskiyou Blvd Ashland OR
Fully refundableReserve now, pay when you stay
The price is ฿3,642 per night from 10 May to 11 May
฿3,642
฿4,061 total
10 May - 11 May
includes taxes & fees
9.4/10 Exceptional! (1,758 reviews)
This was advertised in Orbitz as "pet friendly". Upon my arrival I was asked to pay $35 per pet, as a previously UNDISCLOSED fee.
Reviewed on 5 May 2026
Prospero's Flagship Inn
1193 Siskiyou Blvd Ashland OR
Fully refundableReserve now, pay when you stay
The price is ฿2,043 per night from 7 May to 8 May
฿2,043
฿2,278 total
7 May - 8 May
includes taxes & fees
8.8/10 Excellent! (1,301 reviews)
This hotel is located about a mile south of central Ashland (where the Oregon Shakespeare Festival is), and it was considerably cheaper than anything else in the area. Even though it wasn't expensive, it offered a good-size, clean, quiet room in a good location for us. The entire staff (Melissa, ...
Reviewed on 6 May 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
Ashland Library
Ashland Library is just one of the places to see in Ashland, so why not enjoy the other things to explore during your travels? Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants.
What to do in Ashland
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
