Ashland Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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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

3 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 hotels in Historic Downtown District

Top hotels in Ashland

Stratford Inn
Stratford Inn
2.5 out of 5
555 Siskiyou Blvd, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is S$120 per night from 2 Dec to 3 Dec
S$120
includes taxes & fees
2 Dec - 3 Dec
9/10 Wonderful! (1,392 reviews)
"This hotel is older and has some charm. Very well maintained and CLEAN. (I was so relieved that it was surprisingly clean for an older hotel.) the pool was perfect. We really enjoyed our stay and will definitely be coming back. Our son is in college in the area and this place was just perfect. Quality ..."

Reviewed on 17 Nov,2024

Stratford Inn
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 S$154 per night from 1 Dec to 2 Dec
S$154
includes taxes & fees
1 Dec - 2 Dec
9/10 Wonderful! (1,481 reviews)
"We enjoyed our stay quite a bit. We found the upgrade from the previous owner very appealing (a bit of a relief, frankly) and would definitely consider returning."

Reviewed on 17 Nov,2024

Ashland Hills Hotel & Suites
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 S$240 per night from 25 Nov to 26 Nov
S$240
includes taxes & fees
25 Nov - 26 Nov
9.2/10 Wonderful! (1,004 reviews)
"Absolutely amazing hotel. We had a perfect room that was quiet. Staff went above and beyond to ensure out stay was great."

Reviewed on 20 Nov,2024

Ashland Springs Hotel
See all 718 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.

What to do in Ashland

Salem Puzzling Adventure

Ashland Puzzling Adventure

S$46
Per adult
Ashland Puzzling Adventure
Ashland Team Trivia Hunt: New 2024 Mobile Game App!

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

S$55
Per adult
Ashland Team Trivia Hunt: New 2024 Mobile Game App!
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.