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Check availability on Ashland Winery Hotels

Tonight
4 Dec - 5 Dec
Tomorrow
5 Dec - 6 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Ashland Winery Hotels

Panoramic Room, 1 King Bed, Jetted Tub, Mountain View | Terrace/patio
Callahan's Mountain Lodge

Callahan's Mountain Lodge

3.0 star property
Ashland
8.8 out of 10, Excellent, (1170)
"Great old lodge. Fun rooms with Jacuzzi tubs and fireplace. Restaurant was great and reasonably priced."
United States
Janet
The price is 2.705.870 ₫
3.142.053 ₫ total
includes taxes & fees
9 Dec - 10 Dec
Callahan's Mountain Lodge
Exterior detail
Stratford Inn

Stratford Inn

2.5 star property
Siskiyou-Hargadine Historic District
9.4 out of 10, Exceptional, (1590)
"Friendly staff, nice hot tub.clean room."
United States
Ann
The price is 2.373.570 ₫
2.646.531 ₫ total
includes taxes & fees
8 Dec - 9 Dec
Stratford Inn
Lobby
The Bard's Inn, BW Signature Collection by Best Western

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

2.5 star property
Historic Downtown District
8.6 out of 10, Excellent, (1010)
"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"
United States
Suzanne
The price is 2.769.429 ₫
3.087.913 ₫ total
includes taxes & fees
9 Dec - 10 Dec
The Bard's Inn, BW Signature Collection by Best Western
Free daily full breakfast
Country Willows Inn and Estate

Country Willows Inn and Estate

4.0 star property
Ashland
9.8 out of 10, Exceptional, (33)
"Beautiful setting close to downtown. Pool is marvelous!"
United States
Carol
Country Willows Inn and Estate
Honeymoon Suite #7, 1 Queen Bed, Jetted Tub, Mountain Views | Premium bedding, pillow-top beds, individually decorated
The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges

2.0 star property
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. "
United States
Matthew
The Peerless Hotel by WanderLodges
City Bungalow, Garden Area | Private kitchen | Oven, stovetop, dishwasher, toaster
Hanna's House by WanderLodges

Hanna's House by WanderLodges

4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (2)
"This is a true gem!!! "
United States
Deirdre
The price is 3.247.044 ₫
5.602.544 ₫ total
includes taxes & fees
3 Jan - 4 Jan 2026
Hanna's House by WanderLodges
Luxury House, 2 Bedrooms, Bathtub, Garden Area | Private kitchen | Full-sized fridge, microwave, oven, stovetop
Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges

4.0 star property
Ashland
10.0 out of 10, Exceptional, (6)
"Great ~ memorable stay. "
United States
Melissa
The price is 3.655.298 ₫
7.466.259 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Barclay Klum House by WanderLodges
Abigail Rockefeller | Egyptian cotton sheets, premium bedding, pillow-top beds
Abigail’s Bed & Breakfast Inn

Abigail’s Bed & Breakfast Inn

3.5 star property
Skidmore Academy Historic District
9.4 out of 10, Exceptional, (62)
"Best B and B in Ashland we have ever stayed at in thirty years . Amazing food and very comfortable."
United States
Andrew
The price is 4.747.140 ₫
5.293.061 ₫ total
includes taxes & fees
3 Jan - 4 Jan 2026
Abigail’s Bed & Breakfast Inn
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.
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Top Ashland Hotel Reviews

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