Historic Downtown District Holidays

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Your Historic Downtown District Holiday

Discover the unique character of Historic Downtown District with a customised Historic Downtown District holiday package. From its history to its dining and beyond, this neighbourhood offers plenty of opportunities for adventure and fun. When it's time to explore the sights, you'll find lots of popular attractions nearby including Southern Oregon University, Oregon Shakespeare Festival and Lithia Park. Tick off one or all during your trip to Historic Downtown District. No matter what your dream Historic Downtown District holiday may look like, you can make it a reality with Expedia.

Our guide on 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
A rusted metal bridge in a forested area.

Historic Railroad District

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

Find hotels in Historic Railroad District

Our pick of the best Historic Downtown District Hotel Deals

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 AU$219 per night from 5 July to 6 July
AU$219
5 July - 6 July
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"What a pleasant stay! Very clean and quiet and quaint. Always love Ashland."

Reviewed on 29 June 2026

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 AU$328 per night from 26 July to 27 July
AU$328
26 July - 27 July
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"Loved the old hotel. Front desk people were very kind & helpful. Our room was small but well appointed & spotlessly clean. Location was ideal, right in the middle of Ashland. The Shakespeare theaters were a block away. We will stay again."

Reviewed on 29 June 2026

Ashland Springs Hotel
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St. Ashland OR
The price is AU$398 per night from 6 July to 7 July
AU$398
6 July - 7 July
includes taxes & fees
Winchester Inn
See all 707 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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

9.2/5 (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.
See properties

Activities

Rogue River

Rogue River Family Float & Discovery Park-Rafting and Kayaking

AU$155
per adult
Rogue River Family Float & Discovery Park-Rafting and Kayaking
Rogue River Gold Nugget Section

Rogue River Whitewater Rafting- Mid Day

AU$162
per adult
100% of travellers recommend
Rogue River Whitewater Rafting- Mid Day
Rogue River Whitewater- Half Day Rafting

Rogue River Whitewater- Morning Rafting Adventure

AU$148
per adult
Rogue River Whitewater- Morning Rafting Adventure
See all activities in Ashland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.