Historic Downtown District Trip

Book a Hotel + Flight or Car together to unlock savings

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

If you're spending some time in Historic Railroad District, Crater Lake National Park and Lithia Park are top sights worth seeing.

Find hotel + flight trips 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 ₹9,646 per night from 27 Sep to 28 Sep
₹9,646
per night
27 Sep - 28 Sep
9/10 Wonderful! (1,005 reviews)
"We loved everything about this beautiful hotel and the community. Will definitely stay again soon."

Reviewed on 20 Sep 2023

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 ₹10,800 per night from 15 Oct to 16 Oct
₹10,800
per night
15 Oct - 16 Oct
8.8/10 Excellent! (1,001 reviews)
"Nice and quiet and close to all necessary things."

Reviewed on 12 Sep 2023

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 ₹22,838 per night from 26 Sep to 27 Sep
₹22,838
per night
26 Sep - 27 Sep
9.6/10 Exceptional! (179 reviews)
5 stars all the way
"I was attending a show at the Oregon Shakespeare Festival with my husband and we only stayed one night. Its a 2 min walk to the venue. We were in the heart of downtown, close to restaurants and shops. Our room was pleasantly comfortable, bathroom is spacious and well stocked. The complimentary breakfast ..."

Reviewed on 13 Aug 2023

Winchester Inn
See all 496 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

Image for 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
Image for Mount Ashland Ski Area

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
Image for Allen Elizabethan Theatre

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

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