Ashland Vacation Packages
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Your Ashland Vacation
Create your own exciting adventure with a tailor-made vacation package to Ashland. Its cultural experiences, progressive thinking and spectacular views are just the start of what you can expect in this interesting city. Ready to explore your surroundings? Oregon Shakespeare Festival, Southern Oregon University and Lithia Park are just three of the best places to visit during a trip to Ashland. No matter your travel plans or the size of your budget, putting together a tailored Ashland vacation is simple with Expedia.
Top Ashland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Comfort Inn Yreka I-5
Price was CA $1,327, price is now CA $1,284 per person
CA $1,284
per person
May 22 - May 25
found 9 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Medford (MFR)
7.4/10 Good! (281 reviews)
Staff at check-in was helpful. I had requested a room on the quiet side/away from the freeway, but the room assigned was on the freeway side. They quickly checked and found a different room on the parking lot side. Thank you! Unfortunately, the vent fan in the bathroom did not work! The room was clean and the bed comfortable. The breakfast was typical and adequate. I stayed there for 9 days! Not once was the room serviced, the trash was never collected, towels never replaced!! I mentioned this to the front desk staff at check out: he commented that not that it is acceptable, but there was a recent change in management and front desk staff, and that evidently all the communication issues have not yet been ironed out! Nice to hear, but as he stated, not acceptable service.
Reviewed on Mar 27, 2026
Klamath Motor Lodge
Price was CA $1,238, price is now CA $1,221 per person
CA $1,221
per person
May 22 - May 25
found 9 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Medford (MFR)
8.4/10 Very Good! (1,001 reviews)
A step back in time to an older motel property. We were so pleased to have stayed at this place. Wonderful staff,
clean both property and our room. Very quiet at night.
Property well lit and secure.
We will return given the opportunity.
Reviewed on Apr 4, 2026
Where to stay in Ashland
Find the best Ashland areas and neighborhoods for the activities you enjoy most. Learn more about Ashland
Historic Downtown District
4 out of top 10 points of interest in this area
4.5/5(2 area reviews)
If you're spending some time in Historic Downtown District, Allen Elizabethan Theatre and Thomas Theatre are top sights worth seeing.
Ashland Hotel Deals
Stratford Inn
555 Siskiyou Blvd Ashland OR
The price is CA $138 per night from Apr 13 to Apr 14
CA $138
CA $154 total
Apr 13 - Apr 14
includes taxes & fees
9.4/10 Exceptional! (1,742 reviews)
Great
Reviewed on Apr 6, 2026
Ashland Springs Hotel
212 E Main St Ashland OR
The price is CA $145 per night from Apr 13 to Apr 14
CA $145
CA $184 total
Apr 13 - Apr 14
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
This historic hotel is beautiful and immaculate. It’s so close to all the theaters, restaurants and shopping also! Would highly recommend.
Reviewed on Apr 6, 2026
Ashland Hills Hotel & Suites
2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
The price is CA $129 per night from Apr 19 to Apr 20
CA $129
CA $158 total
Apr 19 - Apr 20
includes taxes & fees
8.8/10 Excellent! (1,450 reviews)
I was very disappointed that you have discontinued your breakfast. I understand the staffing and expense side, and that is I’m sure considerable. However the convenience for your guests is also very considerable. The option you have in place is both expensive and not very appetizing. ( it was not ...
Reviewed on Apr 6, 2026
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.
Discover the most popular places to visit in Ashland
Thomas Theatre
You can get tickets for a performance at Thomas Theatre on your trip to Ashland. Experience the area's acclaimed theater scene and lively festivals.
What to do in Ashland
Explore a world of travel with Expedia
- Hotels near Allen Elizabethan Theatre
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- Visit Skidmore Academy Historic District
- Azalea Park
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
