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.
Prospero's Flagship Inn
Price was CA $1,904, price is now CA $1,600 per person
CA $1,600
per person
Jun 19 - Jun 25
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Medford (MFR)
8.8/10 Excellent! (1,307 reviews)
Perfect place for a one-night stay off the 5! Delightful, clean room, loved the Shakespeare theme, and the staff were very sweet and helpful. Will stay here again and recommend to friends passing through Ashland!
Reviewed on May 14, 2026
Callahan's Mountain Lodge
Price was CA $2,023, price is now CA $1,628 per person
CA $1,628
per person
Jun 19 - Jun 25
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Medford (MFR)
8.8/10 Excellent! (1,167 reviews)
We really love the place. We will keep returning to it. Every chance we get.
Reviewed on May 14, 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
If you're spending some time in Historic Downtown District, Allen Elizabethan Theatre and Oregon Shakespeare Festival are top sights worth seeing.
Ashland Hotel Deals
Prospero's Flagship Inn
1193 Siskiyou Blvd Ashland OR
Fully refundableReserve now, pay when you stay
The price is CA $82 per night from May 25 to May 26
CA $82
CA $92 total
May 25 - May 26
includes taxes & fees
8.6/10 Excellent! (1,314 reviews)
Was a very cute spot to stay the night at. I like that they had all the amenities. Mini fridge, hair dryer, iron, microwave, because I really needed to warm up left overs and my baby's water for his formula. Breakfast area could use some work. Waffle maker was a bit troublesome. And there wasn't ...
Reviewed on May 18, 2026
Ashland Hills Hotel & Suites
2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
The price is CA $160 per night from May 19 to May 20
CA $160
CA $192 total
May 19 - May 20
includes taxes & fees
8.8/10 Excellent! (1,472 reviews)
Great place
Reviewed on May 16, 2026
The Bard's Inn, BW Signature Collection by Best Western
132 N Main Street Ashland OR
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from May 25 to May 26
CA $151
CA $168 total
May 25 - May 26
includes taxes & fees
8.6/10 Excellent! (1,019 reviews)
The staff was excellent! Room was nice and the breakfast was great.
Reviewed on May 18, 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 entertainment choices.
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
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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.
