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
Mosby Creek Covered Bridge in Cottage Grove, Oregon, United States

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

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$169 per night from 17 May to 18 May
AU$169
17 May - 18 May
includes taxes & fees
8.6/10 Excellent! (1,016 reviews)
My stay was excellent on all points, until I went to check out and found a cockroach in the bathroom. When I returned the key to the front desk I reported the cockroach finding and the clerk assured me they’d look into it.

Reviewed on 15 May 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
Fully refundableReserve now, pay when you stay
The price is AU$183 per night from 25 May to 26 May
AU$183
25 May - 26 May
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
Perfect place to stay in Ashland. It’s a nice historic hotel in a great location.

Reviewed on 14 May 2026

Ashland Springs Hotel
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St. Ashland OR
The price is AU$428 per night from 19 May to 20 May
AU$428
19 May - 20 May
includes taxes & fees
9.6/10 Exceptional! (275 reviews)
A lovely place to land. Beautiful Victorian with a garden to relax in. The room was so comfortable (even had a window seat) and the food was great. As was each member of the staff.

Reviewed on 2 May 2026

Winchester Inn
See all 712 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.

Discover the most popular places to visit in Historic Downtown District

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
USA, Oregon, Mt Ashland. Fresh snow on evergreens.

Mount Ashland Ski Area

Hit the slopes in Ashland with a visit to Mount Ashland Ski Area. Discover the top-notch restaurants and entertainment choices in this walkable area.

Mount Ashland Ski Area

Activities

An Audio Tour Through the Heart of Ashland, Oregon

The Cultural Heart of Ashland: A Self-Guided Audio Tour

AU$14
per adult
The Cultural Heart of Ashland: A Self-Guided Audio Tour
Ashland: Cultural History Walking Tour

Ashland: Cultural History Walking Tour

AU$28
per adult
Ashland: Cultural History Walking Tour
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.