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

3 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

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
The price is S$54 per night from 20 Nov to 21 Nov
S$54
20 Nov - 21 Nov
includes taxes & fees
8.6/10 Excellent! (1,152 reviews)
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Reviewed on 15 Nov, 2025

Flagship Inn of 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$144 per night from 17 Dec to 18 Dec
S$144
17 Dec - 18 Dec
includes taxes & fees
8.8/10 Excellent! (1,495 reviews)
Great room location to courtyard to take family pup out side. Quiet. Comfy bed

Reviewed on 10 Nov, 2025

Ashland Hills Hotel & Suites
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
Fully refundable
The price is S$131 per night from 15 Dec to 16 Dec
S$131
15 Dec - 16 Dec
includes taxes & fees
9.2/10 Wonderful! (1,577 reviews)
We loved our stay. The room was huge! 2 queen beds, kitchenette, nook. The mattress was perfect and my wife had her best sleep in years. All of the staff were helpful with the woman taking care of the breakfast room a true highlight. We highly recommend this hotel. It is older, but managed with exceptional ...

Reviewed on 13 Nov, 2025

Stratford Inn
See all 764 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

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

S$55
per adult
Ashland Team Trivia Hunt: New 2024 Mobile Game App!
Salem Puzzling Adventure

Ashland Puzzling Adventure

S$45
per traveller
Ashland Puzzling Adventure
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.