Historic Downtown District Holidays
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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
Siskiyou-Hargadine Historic District
If you're spending some time in Siskiyou-Hargadine Historic District, Lithia Park and Ashland Library are top sights worth seeing.
Historic Railroad District
While Historic Railroad District isn't home to many top sights, Allen Elizabethan Theatre and Thomas Theatre are some notable places to visit nearby.
Skidmore Academy Historic District
While Skidmore Academy Historic District may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Allen Elizabethan Theatre and Thomas Theatre.
Top hotels in Historic Downtown District
The Bard's Inn, BW Signature Collection by Best Western
132 N Main Street Ashland OR
Fully refundableReserve now, pay when you stay
Rp3.024.772
Rp3.372.690 total
10 Aug - 11 Aug
includes taxes & fees
8.6/10 Excellent! (1,012 reviews)
"Really enjoyed our stay. When we pass through Ashland the next time, definitely staying there..."
Reviewed on 9 Aug 2026
Ashland Springs Hotel
212 E Main St Ashland OR
Rp3.284.278
Rp3.949.142 total
17 Aug - 18 Aug
includes taxes & fees
9.2/10 Wonderful! (1,017 reviews)
"Lovely renovated historic downtown hotel that is super close to the Oregon Shakespeare Festival and downtown tourist shop and restaurant area, Clean and cozy room had an exceptionally comfortable bed. I booked a larger room since the typical size of rooms in these historic hotels is smaller. The ..."
Reviewed on 9 Aug 2026
Winchester Inn
35 S. 2nd St. Ashland OR
Rp3.181.095
Rp3.867.814 total
16 Aug - 17 Aug
includes taxes & fees
9.6/10 Exceptional! (283 reviews)
"Everything was perfect"
Reviewed on 6 Aug 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.
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.
Stay near popular Historic Downtown District attractions
Oregon Shakespeare Festival
9.2/10 (620 reviews)
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.
Thomas Theatre
9.4/10 (144 reviews)
You can get tickets for a performance at Thomas Theatre during your trip to Ashland. Experience the area's entertainment choices and lively festivals.
Allen Elizabethan Theatre
9.4/10 (131 reviews)
You can enjoy a show at Allen Elizabethan Theatre during your trip to Ashland. Wander around the area's picturesque gardens or experience its acclaimed theatre scene.
Angus Bowmer Theatre
10.0/10 (11 reviews)
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 lively festivals.
Oregon Cabaret Theatre
9.0/10 (144 reviews)
You can get tickets for a performance at Oregon Cabaret Theatre during your stay in Ashland. Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants.
Things to do
The Cultural Heart of Ashland: A Self-Guided Audio Tour
Rp180.469
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.