Ashland Trip

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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
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Historic Downtown District

3 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.

Find hotels in Historic Downtown District

Top hotels in Ashland

Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 out of 5
1193 Siskiyou Blvd Ashland OR
Fully refundableReserve now, pay when you stay
The price is ₹4,518 per night from 5 Dec to 6 Dec
₹4,518
₹5,037 total
5 Dec - 6 Dec
includes taxes & fees
8.6/10 Excellent! (1,162 reviews)
Clean and comfortable, but bring your own pillow if you are a side sleeper

Reviewed on 20 Nov 2025

Flagship Inn of Ashland
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
Fully refundable
The price is ₹7,983 per night from 2 Dec to 3 Dec
₹7,983
₹8,902 total
2 Dec - 3 Dec
includes taxes & fees
9.2/10 Wonderful! (1,585 reviews)
Such friendly people! It was a pleasure to check in and our room is lovely! Many amenities, plus a pretty pool, an easy TV, generous kitchen appliances, and comfy bed. We'll definitely stay here again!

Reviewed on 20 Nov 2025

Stratford Inn
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
The price is ₹8,010 per night from 23 Nov to 24 Nov
₹8,010
₹9,818 total
23 Nov - 24 Nov
includes taxes & fees
8.8/10 Excellent! (1,501 reviews)
Staff were extremely helpful and friendly, and the room was clean and comfortable.

Reviewed on 19 Nov 2025

Ashland Hills Hotel & Suites
See all 767 properties in Ashland
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

Oregon Shakespeare Festival

Oregon Shakespeare Festival

You can get tickets for a performance at Oregon Shakespeare Festival during your trip to Ashland. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants.

Oregon Shakespeare Festival

Southern Oregon University

Walk around the campus at Southern Oregon University during your visit to Ashland. Experience the area's acclaimed theatre scene and entertainment choices.

Southern Oregon University
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.