Find Winery Hotels in Ashland, OR
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Top Ashland Winery Hotels
Callahan's Mountain Lodge
Ashland
8.8 out of 10, Excellent, (1170)
"Great old lodge. Fun rooms with Jacuzzi tubs and fireplace. Restaurant was great and reasonably priced."
Janet
The price is SAR 385
SAR 447 total
includes taxes & fees
9 Dec - 10 Dec
Stratford Inn
Siskiyou-Hargadine Historic District
9.4 out of 10, Exceptional, (1594)
"Friendly staff, nice hot tub.clean room."
Ann
The price is SAR 338
SAR 377 total
includes taxes & fees
8 Dec - 9 Dec
The Bard's Inn, BW Signature Collection by Best Western
Historic Downtown District
8.6 out of 10, Excellent, (1004)
"The Bards Inn is lovely with each room themed after a Shakespe Play. Location is excellent just at the top of Main St. I can highly recommend this hotel"
Suzanne
The price is SAR 394
SAR 439 total
includes taxes & fees
14 Dec - 15 Dec
Country Willows Inn and Estate
Ashland
9.8 out of 10, Exceptional, (33)
"Beautiful setting close to downtown. Pool is marvelous!"
Carol
The Peerless Hotel by WanderLodges
Historic Railroad District
9.6 out of 10, Exceptional, (95)
"A lovely spot to stay! Our room was beautifully furnished and cozy with a historic charm. The outdoor balcony was a great way to wake up with a cup of coffee. Within walking distance of the theaters and downtown. "
Matthew
Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.
Ashland
10.0 out of 10, Exceptional, (31)
"Can't say enough good things about our stay here! This space is so thoughtfully hosted and arranged. We stayed for two nights in between camping stints in some national parks, and we especially appreciated the luxuriously comfortable beds and well-stocked kitchen tools as we refreshed ourselves, ate a couple of home-cooked meals, and took in the adorable downtown nearby."
Katie M.
The price is SAR 537
SAR 960 total
includes taxes & fees
8 Dec - 9 Dec
Arden Forest Inn
Ashland
9.8 out of 10, Exceptional, (103)
"Beautiful property, great location, friendly owner."
Brian
Hanna's House by WanderLodges
Historic Railroad District
10.0 out of 10, Exceptional, (2)
"This is a true gem!!! "
Deirdre
The price is SAR 425
SAR 754 total
includes taxes & fees
3 Jan - 4 January 2026
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.
Top Ashland Hotel Reviews
Lithia Springs Resort
10/10 Excellent
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Hotels near popular Ashland Attractions
- Hotels near Oregon Shakespeare Festival
- Hotels near Southern Oregon University
- Hotels near Mount Ashland Ski Area
- Hotels near Lithia Park
- Hotels near Thomas Theatre
- Hotels near Howard Prairie Lake
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Ashland Hotels by Star Rating
Explore more hotels
- Holiday Inn Express & Suites Ashland by IHG
- Callahan's Mountain Lodge
- Timbers INN and Suites
- Winchester Inn
- Ashland Commons Hostel
- Relax Inn At Ashland
- Ashland Motel - Oregon
- McCall House Boutique Inn
- Country Willows Inn and Estate
- Cedarwood Inn of Ashland
- Palm Cottages
- The Peerless Hotel by WanderLodges
- Chateau Herbe ~ Athens Room
- Arden Forest Inn
- Abigail’s Bed & Breakfast Inn
- Grandview of Ashland
- Barclay Klum House by WanderLodges
- Rogue Regency Inn and Suites
- My Place Hotel-Medford OR
- Motel 6 Medford, OR - North