Historic Downtown District Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Your Historic Downtown District Holiday
History, dining, adventure, fun — you'll find all that and a whole lot more in Historic Downtown District. Experience the best of this neighbourhood with a holiday package to Historic Downtown District. Kick start your trip to Historic Downtown District by heading to nearby attractions such as Oregon Shakespeare Festival, Southern Oregon University and Lithia Park. Stop daydreaming and start doing. When you're ready to book your holiday to Historic Downtown District, Expedia will help get you there.
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
Siskiyou-Hargadine Historic District
If you're spending some time in Siskiyou-Hargadine Historic District, Lithia Park and Ashland Library are top sights worth seeing.
Historic Railroad District
While Historic Railroad District isn't home to many top sights, Allen Elizabethan Theatre and Thomas Theatre are some notable places to visit nearby.
Skidmore Academy Historic District
While Skidmore Academy Historic District may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Allen Elizabethan Theatre and Thomas Theatre.
Top hotels in Historic Downtown District
The Bard's Inn, BW Signature Collection by Best Western
132 N Main Street Ashland OR
Fully refundableReserve now, pay when you stay
£139
16 Aug - 17 Aug
includes taxes & fees
Ashland Springs Hotel
212 E Main St Ashland OR
Fully refundableReserve now, pay when you stay
£160
13 Sept - 14 Sept
includes taxes & fees
Winchester Inn
35 S. 2nd St. Ashland OR
£151
16 Aug - 17 Aug
includes taxes & fees
9.6/10 Exceptional! (283 reviews)
"Everything was perfect"
Reviewed on 6 Aug 2026
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 travel package cost?
Maybe less than you imagined — from as low as , as a matter of fact! By combining flights, hotels and car rentals into a custom-made package, your Historic Downtown District escape is only clicks away.
If I'm not able to travel, can I cancel my Historic Downtown District travel package?
Don't worry if you're rethinking your Historic Downtown District travel package — you can cancel or change your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We realise life can sometimes throw a spanner in the works, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we'll be here to help.
How do I get a cheap travel package to Historic Downtown District?
Find flights that fit your busy schedule, add a hotel room to your booking and watch the savings grow with a Historic Downtown District travel package. It's as easy as that! From hotels and flights to tours and rental cars, Expedia makes travelling cheap and easy. And with more than 550 partner airlines and 1,000,000 hotels across the globe to choose from, you won't be short of choice.
Does Expedia offer Book Now, Pay Later Historic Downtown District holidays?
Expedia has joined forces with online lender Klarna to make your next break easier on your bank balance. Paying in instalments means you can spread the costs of your dream holiday, leaving you with more cash to spend while you're travelling. Klarna has several payment plans to pick from, so you're sure to find one that fits your budget. Check out these flexible payment options:
- Pay monthly holidays: Realise your holiday dreams sooner with Klarna's manageable monthly instalment plans. If paying bite-sized amounts each month sounds right for you, choose this option during the checkout process.
- Pay in instalments holidays: If you'd prefer to pay off your getaway across multiple transactions, holidays paid in instalments might be the right option for your Book Now, Pay Later holiday through Klarna.
- Low deposit holidays: If paying a small percentage of your getaway (rather than all of it upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan with Klarna.
How far in advance should I book my Historic Downtown District holiday?
While not all airlines release tickets early, it's usually possible to compare international fares on Expedia up to a year in advance. This is the time you can bag some incredible bargains. If you've left things to the last minute, you might still get lucky. Low prices sometimes appear just weeks prior to departure.
What does an Expedia Historic Downtown District travel package include?
Hotels, rental cars and flights — you'll discover them all here. With Expedia, you can create your Historic Downtown District package just the way you want. All you have to do is decide just what you need. Once you've made your booking, you can add on extras like tours and activities. The more you bundle, the bigger your savings!
What should I know before booking a Historic Downtown District travel package?
Bundling your bookings into a Historic Downtown District travel package is the most convenient way to organise your trip. Not only that, you'll get great discounts just for combining your hotels, flights and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with a Historic Downtown District Expedia travel package?
Expedia offers access to more than 550 airline partners worldwide, so you certainly can. Simply choose the carrier you want and craft your ideal Historic Downtown District trip.
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.
Allen Elizabethan Theatre
9.4/10 (131 reviews)
You can enjoy a show at Allen Elizabethan Theatre during your trip to Ashland. Wander around the area's picturesque gardens or experience its acclaimed theatre scene.
Oregon Cabaret Theatre
9.0/10 (144 reviews)
You can get tickets for a performance at Oregon Cabaret Theatre during your stay in Ashland. Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants.
Thomas Theatre
9.4/10 (144 reviews)
You can get tickets for a performance at Thomas Theatre during your trip to Ashland. Experience the area's entertainment choices and lively festivals.
Angus Bowmer Theatre
10.0/10 (11 reviews)
You can make plans for a show at Angus Bowmer Theatre during your trip to Ashland. Wander around the area's picturesque gardens or experience its lively festivals.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.