Explore 18 Luxury Hotels in Ashland

Name: Flagship Inn of Ashland
Price range: $66 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

$134 nightly

$136 total

Nov 4 - Nov 5

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! (1,007 reviews)

Did not have time for breakfast, sorry they are no longer serving the delicious homemade scones in the afternoon.

Reviewed on Oct 18, 2025

Ashland Springs Hotel

212 E Main St, Ashland, OR

Fully refundableReserve now, pay when you stay

$120 nightly

$134 total

Nov 3 - Nov 4

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! (1,007 reviews)

Lovely music & coffee on the mezzanine in a.m. Beautiful decor. Comfortable bedding. Tea & cookies on the mezzanine in the afternoon. An orientation to amenities on arrival would have been helpful.

Reviewed on Oct 4, 2025

Best Western Windsor Inn

2520 Ashland St, Ashland, OR

Fully refundableReserve now, pay when you stay

$98 nightly

$109 total

Nov 1 - Nov 2

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! (1,012 reviews)

Very picturesque, large hotel, huge breakfast room, nice swimming pool, lots of parking, just off I5, the only downsides were no mini-fridge or microwave in the rooms,

Reviewed on Oct 18, 2025

Ashland Hills Hotel & Suites

2525 Ashland St, Ashland, OR

Fully refundableReserve now, pay when you stay

$121 nightly

$135 total

Oct 26 - Oct 27

Total with taxes and fees

2 outdoor tennis courts, an outdoor pool, and a hot tub are all featured at this smoke-free hotel. There's a free ski shuttle, and ski passes and ski storage ...

8.8/10 Excellent! (1,494 reviews)

The front desk staff was exceptionally nice. Parking lot and self parking great. Property was clean. This is definitely a VINTAGE hotel. Design from the 1968-1975 timeframe. I believe rather than remodel things, they designed the hotel around this 1970s vintage theme. For example our bathroom had ...

Reviewed on Oct 18, 2025

Plaza Inn & Suites at Ashland Creek

98 Central Ave, Ashland, OR

Fully refundableReserve now, pay when you stay

$129 nightly

$144 total

Nov 1 - Nov 2

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 ...

8.6/10 Excellent! (1,014 reviews)

The room was large and clean and air conditioner. Well. Breakfast with some healthy options. The classes is close to downtown. It was very safe.

Reviewed on Oct 21, 2025

Callahan's Mountain Lodge

7100 Old Highway 99 South, Ashland, OR

Fully refundableReserve now, pay when you stay

$126 nightly

$128 total

Nov 11 - Nov 12

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 ...

8.6/10 Excellent! (1,171 reviews)

Beautiful balcony view. The hot tub and fireplace were in great working order. The room was very spacious , with a separate kitchen/living area and bedroom. They provided everything we needed for a quiet romantic getaway.

Reviewed on Oct 21, 2025

Flagship Inn of Ashland

1193 Siskiyou Blvd, Ashland, OR

Fully refundableReserve now, pay when you stay

$59 nightly

$66 total

Oct 27 - Oct 28

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! (1,104 reviews)

Easy check-in and check out, room was clean and comfortable, and breakfast was surprisingly good for such a small property.

Reviewed on Oct 17, 2025

Timbers INN and Suites

1450 Ashland Street, Ashland, OR

Fully refundableReserve now, pay when you stay

$70 nightly

$78 total

Oct 27 - Oct 28

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 ...

8.4/10 Very Good! (1,013 reviews)

This is my second stay here and it was great. Very convenient, the staff was friendly, the room was clean and comfortable. I look forward to coming back next year!

Reviewed on Oct 23, 2025

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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.

More 4 star hotels in Ashland

Inn at the Commons

200 N Riverside Ave, Medford, OR

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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	751 hotels
Lowest Price	$66
Highest Price	$144
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, Flagship Inn of Ashland