Explore 18 Luxury Hotels in Ashland

Name: Prospero's Flagship Inn
Price range: $105 total
Rating: 8.6

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Best Luxury Hotels in Ashland

Lithia Springs Resort

2165 W Jackson Rd Ashland OR

Fully refundableReserve now, pay when you stay

$185 nightly

$187 total

Jul 5 - Jul 6

Total with taxes and fees

This bed & breakfast features an outdoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, ...

9.4/10 Exceptional! (1,012 reviews)

"Breakfasts were wonderful. Guest laundry is free of charge. Suite was very comfortable with lots of natural light."

Reviewed on Jun 11, 2026

Ashland Springs Hotel

212 E Main St Ashland OR

Fully refundableReserve now, pay when you stay

$199 nightly

$222 total

Jun 22 - Jun 23

Total with taxes and fees

A full-service spa, a gym, and a restaurant are all featured at this historic hotel. Traveling on business? Take advantage of the business center and free WiFi ...

9.2/10 Wonderful! (1,010 reviews)

"The room was clean, beds comfortable, and staff friendly. The hotel is charming, and you couldn't ask for a better location -especially since we were seeing a performance at OCT, just a block away. We did breakfast, and while it was worth the $5 price tag, don't expect to be wowed. Pick up some coffee, ..."

Reviewed on Jun 11, 2026

Best Western Windsor Inn

2520 Ashland St Ashland OR

Fully refundableReserve now, pay when you stay

$111 nightly

$124 total

Jun 29 - Jun 30

Total with taxes and fees

This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub ...

9/10 Wonderful! (1,009 reviews)

"Great place"

Reviewed on Jun 11, 2026

Plaza Inn & Suites at Ashland Creek

98 Central Ave Ashland OR

Fully refundableReserve now, pay when you stay

$179 nightly

$200 total

Jun 22 - Jun 23

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of ...

8.8/10 Excellent! (1,015 reviews)

"Great location. Wonderful room and amenities."

Reviewed on Jun 10, 2026

Ashland Hills Hotel & Suites

2525 Ashland St Ashland OR

Fully refundableReserve now, pay when you stay

$158 nightly

$176 total

Jun 29 - Jun 30

Total with taxes and fees

This smoke-free hotel features 2 outdoor tennis courts, an outdoor pool, and a restaurant. Traveling on business? Take advantage of the business center and free ...

8.8/10 Excellent! (1,496 reviews)

"Overall"

Reviewed on Jun 11, 2026

Callahan's Mountain Lodge

7100 Old Highway 99 South Ashland OR

Fully refundableReserve now, pay when you stay

$185 nightly

$188 total

Jun 22 - Jun 23

Total with taxes and fees

This lodge features a restaurant, a gym, and a bar/lounge. Bring the family and enjoy the arcade/game room and kid-friendly dining. There's no skimping on freebies ...

8.8/10 Excellent! (1,145 reviews)

"It was a great experience. The hotel was great and the staff were amazing"

Reviewed on Jun 11, 2026

Timbers INN and Suites

1450 Ashland Street Ashland OR

Fully refundableReserve now, pay when you stay

$90 nightly

$100 total

Jun 15 - Jun 16

Total with taxes and fees

A seasonal outdoor pool, free self parking, and free newspapers are featured at this motel. WiFi in public areas is free. A picnic area and express check-out ...

8.6/10 Excellent! (1,010 reviews)

"Excellent place! Clean and cozy, comfortable bed, good location, friendly staff. Everything you need for a pleasant time in Ashland. Would absolutely stay again :)"

Reviewed on Jun 12, 2026

Prospero's Flagship Inn

1193 Siskiyou Blvd Ashland OR

Fully refundableReserve now, pay when you stay

$95 nightly

$105 total

Jun 16 - Jun 17

Total with taxes and fees

A restaurant and a seasonal outdoor pool are featured at this hotel. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate ...

8.6/10 Excellent! (1,357 reviews)

"Quiet, clean, friendly staff, met my needs"

Reviewed on Jun 12, 2026

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More 4 star hotels in Ashland

Bybee's Historic Inn

883 Old Stage Road Central Point OR

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9.8/10 Exceptional! (10 reviews)

Ashland Luxury Hotels

Do you want to stay at an elegant 5 star hotel for your next getaway? Do you want to be pampered like royalty? When you're ready, the Ashland luxury hotels are the plush oasis you’ve been looking for.

Choose from the best luxury hotels in Ashland to make your stay as comfortable and memorable as possible. Deluxe amenities await you upon check-in—perks like a heated pool, luxurious spa, and 24-hour reception service will cater to your every need, no matter the hour. If you’re tired from the day’s activities and don’t feel like wandering around to look for a meal, sit down to dinner at one of the high-end restaurants on property or contact room service for a sophisticated dining experience in the comfort of your own suite. Getting to and from the airport will be an easy task as well because most of these fancy hotels offer a free shuttle service for easy transportation.

We want you to enjoy your next vacation in style and the top luxury resorts in Ashland will help you do just that. Browse Travelocity right now to find amazing deals on the best luxury hotels and 4 star hotels in Ashland, and plan your next opulent escape.

Ashland hotels essential information

Accommodation	800 hotels
Lowest Price	$100
Highest Price	$222
Popular hotels	Plaza Inn & Suites at Ashland Creek, Ashland Springs Hotel, Ashland Hills Hotel & Suites, Callahan's Mountain Lodge, Timbers INN and Suites, Lithia Springs Resort, Best Western Windsor Inn, Prospero's Flagship Inn

Popular Luxury Stays in Ashland

Recent Ashland Hotel Reviews By Fellow Wanderers

Timbers INN and Suites

5 out of 5

Posted 9 hours ago

Travelocity Verified Review

"Excellent place! Clean and cozy, comfortable bed, good location, friendly staff. Everything you need for a pleasant time in Ashland. Would absolutely stay again :)"

A verified traveler stayed at Timbers INN and Suites

Ashland Springs Hotel

5 out of 5

Posted 20 hours ago

Travelocity Verified Review

A verified traveler stayed at Ashland Springs Hotel

The Bard's Inn, BW Signature Collection by Best Western

5 out of 5

Posted 21 hours ago

Travelocity Verified Review

"Though it’s not the newest property, (we stayed in the original building) it’s been upgraded and well maintained. This is a prime location if you’re attending OSF and have ever parked on a back street far, far away. No fee for parking, thank you. Affordable. Nice staff. Clean. Above average breakfast ( it’s says Continental, but there are eggs and a pancake machine!) A/C works and the fan creates a moderate white noise for sleep, which we appreciate."

A verified traveler stayed at The Bard's Inn, BW Signature Collection by Best Western