Historic Downtown District Holidays

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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Historic Railroad District

While Historic Railroad District isn't home to many top sights, Thomas Theatre and Oregon Shakespeare Festival are some notable places to visit nearby.

Find hotels in Historic Railroad 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 €96 per night from 4 Jan to 5 Jan
€96
4 Jan - 5 Jan 2026
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
Love this hotel! I am bummed they started charging for breakfast but it is delicious.

Reviewed on 15 Dec 2025

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 €100 per night from 2 Jan to 3 Jan
€100
2 Jan - 3 Jan 2026
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
Ok

Reviewed on 15 Dec 2025

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 €181 per night from 4 Jan to 5 Jan
€181
4 Jan - 5 Jan 2026
includes taxes & fees
9.6/10 Exceptional! (261 reviews)
Beautiful room with comfortable bed. Nice quality bedding.

Reviewed on 26 Oct 2025

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

Allen Elizabethan Theatre

You can enjoy a show at Allen Elizabethan Theatre during your trip to Ashland. Wander around the area's picturesque gardens or experience its entertainment choices.

Allen Elizabethan Theatre

Tashi Choling Buddhist Center

Find out about the history of Ashland with a stop at Tashi Choling Buddhist Center. Wander around the area's picturesque gardens or experience its lively festivals.

Tashi Choling Buddhist Center

Things to do

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

€36
per adult
Ashland Team Trivia Hunt: New 2024 Mobile Game App!
Salem Puzzling Adventure

Ashland Puzzling Adventure

€30
per traveller
Ashland Puzzling 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.