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$182 per night from 28 Sept to 29 Sept
S$182
28 Sept - 29 Sept
includes taxes & fees
8.8/10 Excellent! (1,461 reviews)
"This is our second time staying here and we absolutely love the property the amenities. The only thing we wish is that the breakfast was still available. We were kind of bummed that that was not an option."

Reviewed on 15 Sept, 2025

Ashland Hills Hotel & Suites
Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 out of 5
1193 Siskiyou Blvd, Ashland, OR
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,021 reviews)
"Super comfy bed, nice shower, quiet surroundings."

Reviewed on 16 Sept, 2025

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Flagship Inn of Ashland
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd, Ashland, OR
9.2/10 Wonderful! (1,550 reviews)
"Despite being an older property, rooms were well kept & clean with very comfortable beds & linens. Staff knew what they were doing. It's a well-run hotel. We'd stay again."

Reviewed on 15 Sept, 2025

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Stratford Inn
See all 752 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!
See all activities in Ashland

* 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.