Historic Downtown District Vacations

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

Historic Railroad District

4.5/5(7 area reviews)

Historic Railroad District might not have many top sights, but Oregon Cabaret Theatre and Allen Elizabethan Theatre are two attractions nearby that you can check out.

Find hotels in Historic Railroad District

Historic Downtown District Hotel Deals

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 ￥14,921 per night from Feb 27 to Feb 28
￥14,921
￥18,977 total
Feb 27 - Feb 28
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
Pros—-staff was incredibly kind Great food available for room service through Larks Cons—room was uncomfortably small.. luckily it was only one person but 2 people could not move around comfortably in this room and the bedding MUST be updated. We truly aren’t ones to complain but it might’ve been ...

Reviewed on Feb 23, 2026

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 ￥13,898 per night from Feb 28 to Mar 1
￥13,898
￥15,496 total
Feb 28 - Mar 1
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
The first time we stayed at The Bard's Inn back in 2020 was an amazing experience. The room was extremely nice, service was great, food was great. This time, though, the room was very dingy, with minimal amenities. It looked as though nothing had been done with it in years. The food experience was ...

Reviewed on Feb 17, 2026

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 ￥27,987 per night from Feb 27 to Feb 28
￥27,987
￥33,080 total
Feb 27 - Feb 28
includes taxes & fees
9.6/10 Exceptional! (270 reviews)
The room is fantastic!! Highly recommend!

Reviewed on Jan 15, 2026

Winchester Inn
See all 698 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 vacation 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 vacation 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 vacation?
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 organizing 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 vacation 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 vacation 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 vacation 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

Ashland is probably best known for the Tony Award-winning Oregon Shakespeare Festival, which I highly recommend checking out if you're in to Shakespeare plays. The statue in the photo is actually a guy in a Shakespearean costume collecting contributions toward a permanent statue of the Bard in Ashland. #WeekendGetaway

Oregon Shakespeare Festival

You can make plans for a show 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.