Historic Downtown District Holidays

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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
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

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 £83 per night from 18 May to 19 May
£83
18 May - 19 May
includes taxes & fees
8.6/10 Excellent! (1,015 reviews)
Fine stay. Food was as expected for an included hotel breakfast. Facilities are a bit dated. But clean enough.

Reviewed on 12 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 £98 per night from 25 May to 26 May
£98
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 £244 per night from 25 May to 26 May
£244
25 May - 26 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 701 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

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.

Popular places to visit

Emigrant Lake

Commune with nature and explore the great outdoors at Emigrant Lake during your travels in Ashland. Experience the entertainment choices and lively festivals in this family-friendly area.

Emigrant Lake

Things to do

Ashland: Cultural History Walking Tour

Ashland: Cultural History Walking Tour

£15
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. Flight-inclusive packages are ATOL protected.