Ashland Holidays

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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

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 hotels in Historic Downtown District

Top hotels in Ashland

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$223 per night from 21 Jul to 22 Jul
S$223
21 Jul - 22 Jul
includes taxes & fees
8.8/10 Excellent! (1,446 reviews)
"Really enjoyed this hotel. The grounds and hotel are well kept. While it is a bit of a drive to downtown Ashland, the area felt really safe and was easy to drive to the more populated area. We had our dog with us and this hotel was very dog friendly and accommodating for our pet. My only regret was ..."

Reviewed on 12 Jul, 2025

Ashland Hills Hotel & Suites
Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

2.5 out of 5
434 S. Valley View Rd., Ashland, OR
Fully refundableReserve now, pay when you stay
The price is S$142 per night from 10 Aug to 11 Aug
S$142
10 Aug - 11 Aug
includes taxes & fees
8.6/10 Excellent! (1,022 reviews)
"Great."

Reviewed on 11 Jul, 2025

Comfort Inn & Suites Ashland
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 S$228 per night from 22 Jul to 23 Jul
S$228
22 Jul - 23 Jul
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
"Just returned from my 3rd stay at the Bard's Inn and it will not be the last. I absolutely love everything about this hotel. The location is prime. Very close to downtown shops and restaurants 1-3 minutes. 5 minute walk to Lithia Park. Staff is very friendly. Extremely quiet. I saw other guests but ..."

Reviewed on 13 Jul, 2025

The Bard's Inn, BW Signature Collection by Best Western
See all 739 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.

What to do in Ashland

Salem Puzzling Adventure

Ashland Puzzling Adventure

S$45
per traveller
Ashland Puzzling Adventure
Ashland Team Trivia Hunt: New 2024 Mobile Game App!

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

S$54
per adult
Ashland Team Trivia Hunt: New 2024 Mobile Game App!
Klamath River- Irongate "Kucascas" Dam Scenic Float

Klamath River- Irongate "Kucascas" Dam Scenic Float

S$251
per adult
Klamath River- Irongate "Kucascas" Dam Scenic Float
See all activities in Ashland

Frequently asked questions

How much does an Ashland holiday package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Ashland costs! Our packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Ashland?
If you're looking to score a cheap Ashland holiday package, consider visiting in December, January and February. You'll generally find better prices on accommodation and flights during these quieter months --- perfect for a budget-friendly getaway.
How many days is enough for Ashland?
To fully enjoy an Ashland holiday, we suggest booking for 2 days. Divide your time between discovering Thomas Theatre, Schneider Museum of Art and other major sights, on top of exploring neighbourhoods like Siskiyou-Hargadine Historic District and Historic Railroad District. If you've got some spare time, add a tour or day trip to your Ashland holiday itinerary.
Is it worth booking a holiday package to Ashland?
Whether you want to explore top sights like Oregon Shakespeare Festival and Lithia Park on your Ashland holiday, or coming for its great cafes, cycling and hiking, there's something for everyone here. With so much to see and do, you'll quickly learn why so many travellers think Ashland is a good holiday destination.
How to find the best Ashland package deals?
Bagging a cheap Ashland package deal is easy with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can personalise your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Ashland package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book an Ashland holiday as a package?
You can enjoy significant savings on your Ashland break by booking a tailored holiday package. Click on the "Package" heading, then enter your travel dates and destination to browse the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Ashland?
Score amazing discounts by reserving your flights early with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Ashland trip.
How to plan a trip to Ashland?

  1. Choose your travel dates: The things you plan to do in Ashland and your favourite season will help you decide when to get away.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and food to flights and experiences. Your hotel will likely be the biggest expense during your trip to Ashland.
  3. Decide your trip length: Consider how much time you'd like to spend exploring Ashland. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Combine your airfare and accommodation: After you've settled on your dates and duration, lock in the right Ashland holiday package for you.

* 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.