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.
Paschal Winery
Price was CA $622, price is now CA $544 per person
CA $544
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Medford (MFR)
9.6/10 Exceptional! (13 reviews)
It is a beautiful property. We stayed in the little trailer, glamp cottage and it was so cute. Also enjoyed the private hot tub provided. We did some wine tasting, a flight of white and a flight of reds and enjoyed their fabulous cork and fork dinner. The location is beautiful. My travelling companion said if she didn’t know better she would think she was in Switzerland.
Reviewed on May 3, 2025
Compass by Margaritaville in Medford
Price was CA $749, price is now CA $598 per person
CA $598
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Medford (MFR)
9.6/10 Exceptional! (1,003 reviews)
Room was spotless, friendly staff and very dog friendly
Reviewed on Feb 11, 2026
McCall House Boutique Inn
Historic Downtown District
Price was CA $1,380, price is now CA $1,167 per person
CA $1,167
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Medford (MFR)
9.2/10 Wonderful! (574 reviews)
Great place, quite and very helpful and friendly staff
Reviewed on Feb 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, Thomas Theatre and Oregon Shakespeare Festival are top sights worth seeing.
Ashland Hotel Deals
Stratford Inn
555 Siskiyou Blvd Ashland OR
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,672 reviews)
Great location for the price
Reviewed on Feb 5, 2026
Ashland Springs Hotel
212 E Main St Ashland OR
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from Feb 16 to Feb 17
CA $118
CA $152 total
Feb 16 - Feb 17
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
The Hotel is beautiful and historic. The beds were the most comfortable we had on our travels.
Reviewed on Feb 5, 2026
Ashland Hills Hotel & Suites
2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,471 reviews)
Spotless clean. Great service. Amazing venue and dog friendly
Reviewed on Feb 7, 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 lively festivals and acclaimed theater scene.
Explore a world of travel with Expedia
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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.
