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Featured Ashland 4 Star hotels

Compass by Margaritaville in Medford

2399 S Pacific Hwy Medford OR

Fully refundableReserve now, pay when you stay

CA $211

CA $254 total

Oct 12 - Oct 13

includes taxes & fees

Book a stay at this golf hotel in Medford. Enjoy free breakfast, free parking, and a casino. Our guests praise the breakfast and the pool in our reviews. Popular ...

9.6/10 Exceptional! (1,111 reviews)

"Beds are amazing girl who checked us in.was.so helpful"

Reviewed on Sep 13, 2026

Hummingbird Estate Wine & Suites

1677 Old Stage Rd Central Point OR

CA $207

CA $210 total

Sep 15 - Sep 16

includes taxes & fees

Book a stay at this luxury B&B in Central Point. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Jacksonville Cemetery and Art Presence ...

9.6/10 Exceptional! (185 reviews)

"We stayed in the cottage because the main estate was booked. The main disappointment was that there was a coffee pot and filters but no coffee. Everything else was great! They had a dinner event the 1 night we stayed and the staff was very busy."

Reviewed on Aug 27, 2026

McCall House Boutique Inn

153 Oak St Ashland OR

CA $382

CA $426 total

Oct 12 - Oct 13

includes taxes & fees

Stay at this B&B in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...

9.2/10 Wonderful! (611 reviews)

"This was the second time we stayed here. The staff is excellent and took care of everything we needed before we even arrived. Their breakfast was excellent! We really enjoy staying at the McCall House. Close to everything you might want to do while in Ashland. We walked to everything we wanted to ..."

Reviewed on Sep 13, 2026

Country Willows Inn and Estate

1313 Clay St Ashland OR

Fully refundableReserve now, pay when you stay

CA $351

CA $357 total

Sep 14 - Sep 15

includes taxes & fees

Stay at this B&B in Ashland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Oregon Shakespeare Festival and Weisinger Family Winery are ...

9.8/10 Exceptional! (42 reviews)

"Beautiful property with gardens and a heated pool. Great staff, breakfast was inventive and quite tasty. Is 10 minutes from town but easy to drive and no real parking issues even at play times. We will be back next year"

Reviewed on Sep 10, 2026

Arden Forest Inn

261 W Hersey St Ashland OR

CA $225

CA $251 total

Sep 20 - Sep 21

includes taxes & fees

Stay at this B&B in Ashland. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Oregon Shakespeare Festival and Allen Elizabethan Theatre ...

9.8/10 Exceptional! (112 reviews)

"Wonderful, would stay again and highly recommended. The owner was nice and helpful. The property was cute, quiet and relaxing."

Reviewed on Aug 30, 2026

Barclay Klum House by WanderLodges

1023 E Main St Ashland OR

CA $210

CA $412 total

Sep 28 - Sep 29

includes taxes & fees

Stay at this vacation home in Ashland. Enjoy free WiFi, free parking, and a garden. Popular attractions Oregon Shakespeare Festival and Ashland Library are located ...

10/10 Exceptional! (10 reviews)

"Really nice 2 bedroom apartment in historical house-great applicances, comfortable and spacious living and bedroom areas. We were only two, comfortable for up to 2 couples easily. 10-15 minute walk to downtown along pleasant street. Coffee shop around the corner. Very pleasant and comfortable stay ..."

Reviewed on Sep 12, 2026

Hanna's House by WanderLodges

39 4th St Ashland OR

CA $315

CA $458 total

Sep 27 - Sep 28

includes taxes & fees

Book a stay at this business-friendly vacation home in Ashland. Enjoy free WiFi, free parking, and a garden. Popular attractions Oregon Shakespeare Festival ...

10/10 Exceptional! (4 reviews)

"Next visit to the OSF no question we’ll stay here if available. Short walking distance to everything in downtown Ashland, yet quiet and private."

Reviewed on Aug 2, 2026

Paschal Winery

1122 Suncrest Rd Talent OR

CA $180

CA $574 total

Sep 15 - Sep 16

includes taxes & fees

Book a stay at this luxury cottage in Talent. Enjoy free WiFi, free parking, and an attached winery. Popular attractions Oregon Shakespeare Festival and Paschal ...

9.8/10 Exceptional! (19 reviews)

"The property is at a winery with beautiful views of swans and a new baby swan, and the surrounding vineyards. The grounds are in good condition and the areas next to winery are lush and green with lots of things to look at. The winery itself has good food and even better wine. The Glamp Cottage trailer ..."

Reviewed on Jun 12, 2026

The Mountain Ave House by WanderLodges

78 N Mountain Ave Ashland OR

CA $248

CA $478 total

Sep 14 - Sep 15

includes taxes & fees

Stay at this vacation home in Ashland. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Oregon Shakespeare Festival and North Mountain ...

10/10 Exceptional! (7 reviews)

"This place was a 10/10! Made a big breakfast for my friends. Grocery store very close. I will be returning!"

Reviewed on Sep 27, 2025

#47 The Cabins at Hyatt Lake - Sleeps 5 - Hot Tub

7979 Hyatt Prairie Road Ashland OR

Stay at this cottage in Ashland. Enjoy free WiFi, free parking, and cable/satellite TV service. Popular attractions Hyatt Reservoir and Tub Springs State Park ...

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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.

4 Star Hotels Ashland

Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?

Come on, you deserve it!

The best part about staying in Ashland 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.

Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.

The best four star hotels in Ashland will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!

If you’re looking for 4 star hotels in Ashland, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.

Recent Ashland hotel reviews by fellow wanderers

Ashland Hills Hotel & Suites

5 out of 5

Posted 1 hour ago

Travelocity Verified Review

"The room we had was bery pretty and clean the only thing was the bathroom floor was very slippery because of the tile they have. Otherwise the grounds were pretty. Nice place!"

A verified traveller stayed at Ashland Hills Hotel & Suites