Historic Downtown District Trip

Book a Hotel + Flight or Car together to unlock savings

Photo by Patrick Glassford

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to ₹43,962 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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
Default Image

Historic Railroad District

While Historic Railroad District isn't home to many top sights, Oregon Cabaret Theatre and Allen Elizabethan Theatre are some notable places to visit nearby.

Find hotels in Historic Railroad District

Top hotels in Historic Downtown District

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 ₹13,578 per night from 8 Jul to 9 Jul
₹13,578
₹15,140 total
8 Jul - 9 Jul
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"We loved the location, close to shops, parks and restaurants . Staff was friendly and our room had a nice patio."

Reviewed on 6 Jul 2025

The Bard's Inn, BW Signature Collection by Best Western
Ashland Springs Hotel
Ashland Springs Hotel
3 out of 5
212 E Main St, Ashland, OR
The price is ₹22,411 per night from 14 Jul to 15 Jul
₹22,411
₹25,415 total
14 Jul - 15 Jul
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"Squeaky floors and can hear the neighbors."

Reviewed on 6 Jul 2025

Ashland Springs Hotel
Winchester Inn
Winchester Inn
3.5 out of 5
35 S. 2nd St., Ashland, OR
The price is ₹20,273 per night from 4 Aug to 5 Aug
₹20,273
₹23,794 total
4 Aug - 5 Aug
includes taxes & fees
9.6/10 Exceptional! (247 reviews)
"Beautiful property, really comfortable bed, pillows and sheets!"

Reviewed on 2 Jul 2025

Winchester Inn
See all 652 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

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 acclaimed theatre scene.

Angus Bowmer Theatre

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.

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