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
A rusted metal bridge in a forested area.

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 S$141 per night from 26 Nov to 27 Nov
S$141
26 Nov - 27 Nov
includes taxes & fees
8.4/10 Very good! (1,012 reviews)
"We booked Jere because everything else was taken that was in downtown. The hotel is ok. Breakfast was decent with some variety in terms of protein and fresh fruit. The tvs are out dated so we couldn’t watch Netflix and the property is spread out over 4 buildings at 3 different intersections."

Reviewed on 26 Oct, 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 S$154 per night from 17 Nov to 18 Nov
S$154
17 Nov - 18 Nov
includes taxes & fees
Ashland Springs Hotel
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St. Ashland OR
The price is S$211 per night from 9 Nov to 10 Nov
S$211
9 Nov - 10 Nov
includes taxes & fees
9.6/10 Exceptional! (291 reviews)
"Amazing breakfasts, friendly staff, best location"

Reviewed on 10 Oct, 2026

Winchester Inn
See all 682 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.

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.
See properties

Things to do

An Audio Tour Through the Heart of Ashland, Oregon

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

S$13
per adult
The Cultural Heart of Ashland: A Self-Guided Audio 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.