Hotels in Ashland

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Check prices for these dates

Tonight
Dec 25 - Dec 26
Tomorrow
Dec 26 - Dec 27
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Where to stay in Ashland?

Panoramic Room, 1 King Bed, Jetted Tub, Mountain View | Terrace/patio
Callahan's Mountain Lodge
Callahan's Mountain Lodge
3.0 star property
8.8 out of 10, Excellent, (1169)
  • cleanliness
    Unwind at this Ashland mountain lodge with cozy rooms and outdoor adventures.
The price is $103
$119 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Callahan's Mountain Lodge
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.
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Great weekend hotel deals in Ashland, OR

Showing deals for:Jan 2 - Jan 4

Image gallery for Winchester Inn

Bar (on property)

Winchester Inn

3.5 star property
Ashland
9.8/10Exceptional (262 reviews)
10% off
$181 nightly
Price is $429
Total with taxes and fees
Winchester Inn

Check out pet-friendly hotels in Ashland

Panoramic Room, 1 King Bed, Jetted Tub, Mountain View | Terrace/patio
Callahan's Mountain Lodge

Callahan's Mountain Lodge

Callahan's Mountain Lodge
3.0 star property
Ashland
8.8 out of 10, Excellent, (1169)
The price is $103
$119 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Callahan's Mountain Lodge
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You may also like hotels with pools in Ashland

Free daily on-the-go breakfast
Flagship Inn of Ashland

Flagship Inn of Ashland

Flagship Inn of Ashland
2.5 star property
Ashland
8.8 out of 10, Excellent, (1204)
The price is $63
$70 total
includes taxes & fees
Dec 26 - Dec 27
Flagship Inn of Ashland
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You can also stay at hotels with a hot tub in Ashland

Panoramic Room, 1 King Bed, Jetted Tub, Mountain View | Terrace/patio
Callahan's Mountain Lodge

Callahan's Mountain Lodge

Callahan's Mountain Lodge
3.0 star property
Ashland
8.8 out of 10, Excellent, (1169)
The price is $103
$119 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Callahan's Mountain Lodge
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.
View all properties

When is the best time to visit Ashland?

Our prices for hotels in Ashland are cheapest in January
Price trends for hotels in Ashland
Pricing is based on two traveler single night rates
View properties in December
Currently viewing crowd sizes and weather for December.
Typical weather for Ashland
December
Low crowds
High 7°C / low -2°C. Snow likely.
View properties in December
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December, Low crowds, average high temperature 7 degrees Celsius, average low temperature -2 degrees Celsius. Snow likely.
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January, Low crowds, average high temperature 8 degrees Celsius, average low temperature -2 degrees Celsius. Snow likely.
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February, Low crowds, average high temperature 9 degrees Celsius, average low temperature -1 degrees Celsius. Snow likely.
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March, Moderate crowds, average high temperature 11 degrees Celsius, average low temperature -1 degrees Celsius. Snow likely.
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April, Low crowds, average high temperature 14 degrees Celsius, average low temperature 2 degrees Celsius. Partly sunny.
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May, Moderate crowds, average high temperature 19 degrees Celsius, average low temperature 5 degrees Celsius. Sunny most days.
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June, High crowds, average high temperature 24 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
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July, High crowds, average high temperature 30 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
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August, High crowds, average high temperature 30 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
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September, High crowds, average high temperature 26 degrees Celsius, average low temperature 9 degrees Celsius. Sunny most days.
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October, Moderate crowds, average high temperature 19 degrees Celsius, average low temperature 5 degrees Celsius. Sunny most days.
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November, Moderate crowds, average high temperature 11 degrees Celsius, average low temperature 0 degrees Celsius. Partly sunny.
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Monthly weather averages (˚C)

Top neighborhoods in Ashland

Historic Downtown District

The Historic Downtown District neighborhood offers attractions such as Thomas Theatre and Oregon Shakespeare Festival.

Siskiyou-Hargadine Historic District

The Siskiyou-Hargadine Historic District neighborhood has lots to see including Lithia Park and Ashland Library.

Top landmarks in Ashland

Ashland is probably best known for the Tony Award-winning Oregon Shakespeare Festival, which I highly recommend checking out if you're in to Shakespeare plays. The statue in the photo is actually a guy in a Shakespearean costume collecting contributions toward a permanent statue of the Bard in Ashland. #WeekendGetaway
Photo by Patrick Glassford
Open Photo by Patrick Glassford

Oregon Shakespeare Festival

4.6/5 (351 reviews)
If you want to see a show while you're in town, try and grab some tickets at Oregon Shakespeare Festival in Historic Downtown District. If you enjoy the show and want to see another, Thomas Theatre, Oregon Cabaret Theatre, and Angus Bowmer Theatre are all a short walk away.
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USA, Oregon, Mt Ashland. Fresh snow on evergreens.

Mount Ashland Ski Area

4.2/5 (136 reviews)
Skiers and snowboarders might want to test out the slopes at Mount Ashland Ski Area, a skiing spot located 7.8 mi (12.5 km) from central Ashland.
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Learn more about Ashland

Between Shakespeare and the sublime, this artsy enclave captivates with its cultural punch far beyond its size. The Oregon Shakespeare Festival transforms three theaters into worlds of drama nearly year-round, drawing theater lovers who linger after standing ovations. Main Street's independent boutiques and farm-to-table restaurants showcase local creativity without pretension. Lithia Park unfolds like a living painting—creek-side paths wind through 93 acres where picnickers claim spots beneath ancient trees. Southern Oregon University adds youthful energy to this intellectual haven. After hiking nearby trails, soak tired muscles in Lithia Plaza's mineral-rich fountains (warning: the water tastes terrible). For a perfect day, catch a matinee, browse gallery-quality crafts, then toast the sunset with local wines.

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APB2G7 Shops and restaurants on Lithia Plaza at junction with Main Street in Ashland Oregon

Check out reviews of Ashland hotels guests love

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

10/10 Excellent
"Everything was wonderful Beds were very comfortable. Bedding was so warm. Very spacious and the grounds were also very nice. Loved it . Will recommend to everyone."
Deborah 1-night trip
Posted 1 day ago
Ashland Hills Hotel & Suites

Frequently asked questions

What accommodations do travelers like in Ashland?
Winchester Inn, Country Willows Inn and Estate and McCall House Boutique Inn are all properties that our guests really like.
Where can I find free parking at my hotel in Ashland?
Park your car for free at McCall House Boutique Inn.
Can I book refundable accommodations in Ashland?
If you need the flexibility to change your plans to Ashland, most properties provide refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
Where should I stay in Ashland if I want a cheap accommodation?
An inexpensive option worth considering is Stratford Inn.
Where can I stay in Ashland if I want a vacation rental instead of a traditional hotel?
If you're looking for a good alternative to a hotel, look over our selection of 103 vacation homes. You can also consider one of the 58 apartments or 64 cottages.
What will the weather in Ashland be like during my trip?
The warmest months in Ashland are usually August and July with an average temp of 65°F. December and January are the chilliest months when the average temp is 37°F. The rainiest months are December and March.
Why should I book my Ashland hotel with Hotels.com?
There are plenty of reasons to book your Ashland travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.