Ashland Holidays

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Our guide on where to stay in Ashland

Find the best Ashland areas and neighborhoods for the activities you enjoy most. Learn more about Ashland
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Historic Downtown District

4 out of top 10 points of interest in this area

While visiting Historic Downtown District, you might make a stop by sights like Allen Elizabethan Theatre and Oregon Shakespeare Festival.

Find hotel + flight trips in Historic Downtown District

Our pick of the best Ashland Hotel Deals

Callahan's Mountain Lodge
Callahan's Mountain Lodge
3 out of 5
7100 Old Highway 99 South, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is NZ$216 per night from 25 Jun to 26 Jun
NZ$216
per night
25 Jun - 26 Jun
8.8/10 Excellent! (1,002 reviews)
"It was amazing like always this is the 5th time we have stayed at Callahans we love it"

Reviewed on 19 Jun. 2024

Callahan's Mountain Lodge
Ashland Hills Hotel & Suites
Ashland Hills Hotel & Suites
3 out of 5
2525 Ashland St, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is NZ$287 per night from 7 Jul to 8 Jul
NZ$287
per night
7 Jul - 8 Jul
9/10 Wonderful! (1,516 reviews)
"We like this hotel. It has spacious rooms and a lovely courtyard pool, which is ideal for a couple and extra kids. However, there is a slight mold smell, possibly due to the room being on the first floor/ half basement."

Reviewed on 20 Jun. 2024

Ashland Hills Hotel & Suites
Stratford Inn
Stratford Inn
2.5 out of 5
555 Siskiyou Blvd, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is NZ$228 per night from 30 Jun to 1 Jul
NZ$228
per night
30 Jun - 1 Jul
9/10 Wonderful! (1,513 reviews)
"Overall a really great place. Informative and accessible staff, very clean and well decorated interiors. They even left us a great handwritten note and fresh flowers in our room. I really appreciated that. My only issue was the bedding, which while perfectly clean, was on the older end, with some ..."

Reviewed on 21 Jun. 2024

Stratford Inn
See all 675 properties in Ashland
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 an Ashland holiday package cost?
The most affordable Ashland package is , so your dream escape can become a reality — without it costing a fortune. Bundle flights, hotels, car rentals and more to customize a package suited to your travelling style.
How do I get a cheap travel package to Ashland?
You’ll save tons of cash if you bundle your hotels, car rentals and flights into an Ashland holiday package. Sometimes cheap packages mean fewer options. But not with Expedia. We offer more than 550 air carriers and 1 000 000 hotels throughout the world, which means you’ll always have plenty of variety to choose from. Eager to save even more? Add some interesting activities to your package deal to unlock even more discounts! After all, travel is about more than simply getting to your destination.
Where should I stay in Ashland?
With fascinating attractions such as Oregon Shakespeare Festival and Southern Oregon University in this neighbourhood, try to find a hotel near either of them. Mount Ashland Ski Area is another sight in Ashland that draws the crowds.
What are the top hotels in Ashland?
If you intend to stay in the Historic Railroad District neighbourhood, some top options are Ashland Hills Hotel & Suites and Stratford Inn. Siskiyou-Hargadine Historic District is also a well-known Ashland area. We recommend Plaza Inn & Suites at Ashland Creek or Ashland Springs Hotel if you choose this part of the city.
How far in advance should I book my Ashland holiday?
It’s hard to pick the perfect time for airfares, but we generally suggest the earlier, the better. Plenty of international journeys on Expedia become available to compare up to 12 months in advance. If you’re booking late, don’t fret. Low prices occasionally appear within a few weeks of departure dates.
What does an Expedia Ashland travel package include?
That depends on you. You can select from a range of Ashland packages, such as a flight, hotel and rental car. You can also book a hotel and a flight, or a rental car with a flight. Once you’ve made your booking, you can add the fun stuff like tours and activities. Whatever your perfect Ashland getaway looks like, you’ll save!
What should I know before booking an Ashland travel package?
You’ll land terrific savings when you bundle your flights, hotels and rental cars into a travel package. Not only that, booking everything in one spot makes trip planning easier. So why waste your time or money? Whether you’re organising an upscale romantic escape or a low-cost family road trip, browse our holiday packages today.
Can I choose my airline with an Ashland Expedia holiday package?
Yes, and with more than 550 airlines to select from all over the world, you’ve got lots of choice. Search the available options and see which airline fits your needs and budget.
If I'm not able to travel, can I cancel my Ashland holiday package?
Whether it’s your flight or hotel, yes, you can cancel or amend it. Locked in your Ashland holiday package in the last 24 hours? You may be able to make changes for free. For bookings older than that, you may incur a fee from your hotel, airline or car rental company. For more information, take a look at our Customer Service Portal. We’re here to help you each step of the way.

Discover the most popular places to visit in Ashland

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 lively festivals in this walkable area.

Mount Ashland Ski Area
Image for Southern Oregon University

Southern Oregon University

Walk around the campus at Southern Oregon University during your visit to Ashland. Experience the area's lively festivals and entertainment choices.

Southern Oregon University

More holiday ideas

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.