Historic Downtown District Trip

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Photo by Shannon Willitts

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Where to stay in Historic Downtown District

Find the best Historic Downtown District areas and neighborhoods for the activities you enjoy most. Learn more about Historic Downtown District
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Siskiyou-Hargadine Historic District

1 out of top 10 points of interest in this area

If you're spending some time in Siskiyou-Hargadine Historic District, Lithia Park and Ashland Library are top sights worth seeing.

Find hotels in Siskiyou-Hargadine Historic District

Top hotels in Historic Downtown District

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
Fully refundableReserve now, pay when you stay
The price is ₹7,056 per night from 6 Feb to 7 Feb
₹7,056
₹9,222 total
6 Feb - 7 Feb
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
The room was very comfortable and clean. We also thought the lady running breakfast was kind and efficient.

Reviewed on 9 Jan 2026

Ashland Springs Hotel
The Bard's Inn, BW Signature Collection by Best Western

The Bard's Inn, BW Signature Collection by Best Western

2.5 out of 5
132 N Main Street Ashland OR
Fully refundableReserve now, pay when you stay
The price is ₹10,746 per night from 25 Jan to 26 Jan
₹10,746
₹11,982 total
25 Jan - 26 Jan
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
Clean, great location

Reviewed on 12 Jan 2026

The Bard's Inn, BW Signature Collection by Best Western
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St. Ashland OR
The price is ₹14,978 per night from 18 Jan to 19 Jan
₹14,978
₹17,743 total
18 Jan - 19 Jan
includes taxes & fees
9.6/10 Exceptional! (267 reviews)
The room is fantastic!! Highly recommend!

Reviewed on 15 Jan 2026

Winchester Inn
See all 697 properties in Historic Downtown District
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.

Frequently asked questions

How much does a Historic Downtown District holiday package cost?
The most affordable Historic Downtown District package is , so your dream escape can become a reality — without a hefty price tag. Combine flights, hotels, car rentals and more to custom build a package that suits you.
How do I get a cheap travel package to Historic Downtown District?
Combine your hotels and flights, add on extras such as activities, and save with a Historic Downtown District holiday package. You won't just land impressive discounts on your trip — you'll have loads of choice within your reach too. When you book with Expedia, you can select from more than 550 air carriers and 1,000,000 hotels globally. Your next big adventure begins right here, right now!
How far in advance should I book my Historic Downtown District holiday?
While not all air carriers release tickets early, you can normally start comparing international flights on Expedia up to 12 months in advance. This is the time you can bag some fantastic bargains. If you're booking last minute, you may still be in luck. Sometimes the lowest prices become available only weeks prior to departure.
What does an Expedia Historic Downtown District travel package include?
Flights, hotels and a cool car for all your road trip adventures. Simply choose your preferred bundle and get access to incredible deals. Once you've made your booking, add on some experiences and tours and watch your savings stack up. When it comes to crafting your Historic Downtown District getaway, you're the one in control!
What should I know before booking a Historic Downtown District travel package?
When you book your flights, hotels and car rentals together, you'll pick up great discounts. Whether you're organising a rural escape in a cottage or would rather stay in an upscale city hotel, Expedia will help make it happen.
Can I choose my airline with a Historic Downtown District Expedia holiday package?
Yes, you can. We offer more than 550 partner airlines throughout the world, so pick the carrier that best suits your budget needs.
If I'm not able to travel, can I cancel my Historic Downtown District holiday package?
It's difficult to predict what the future holds, so it's good to know that you can change or cancel your Historic Downtown District holiday package. If your booking was made in the last 24 hours, you may be eligible for a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

Popular places to visit

Ashland is probably best known for the Tony Award-winning Oregon Shakespeare Festival, which I highly recommend checking out if you're in to Shakespeare plays. The statue in the photo is actually a guy in a Shakespearean costume collecting contributions toward a permanent statue of the Bard in Ashland. #WeekendGetaway

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
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

Angus Bowmer Theatre

You can make plans for a show at Angus Bowmer Theatre during your trip to Ashland. Wander around the area's picturesque gardens or experience its entertainment choices.

Angus Bowmer Theatre
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.