Find Winery Hotels in Historic Downtown District, OR

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Historic Downtown District Winery Hotels

This weekend
Next weekend

Our top choices for Historic Downtown District hotels with winery

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, (1003)
"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 NT$3,314
NT$3,695 total
includes taxes & fees
Jan 2 - 2026/1/3
The Bard's Inn, BW Signature Collection by Best Western

Holiday Inn Express Hotel & Suites Medford-Central Point by IHG

Holiday Inn Express Hotel & Suites Medford-Central Point by IHG
2.5 star property
Central Point
9.0 out of 10, Wonderful, (1006)
"Very nice room and the staff accommodated our request for a quiet room. Breakfast was very good, with a nice selection. "
United States
Caren
The price is NT$2,935
NT$3,302 total
includes taxes & fees
Dec 27 - Dec 28
Holiday Inn Express Hotel & Suites Medford-Central Point by IHG

Stratford Inn

Stratford Inn
2.5 star property
Siskiyou-Hargadine Historic District
9.4 out of 10, Exceptional, (1616)
"Great staff, clean, cute place. "
United States
Lynette
The price is NT$2,557
NT$2,851 total
includes taxes & fees
Dec 23 - Dec 24
Stratford Inn

Callahan's Mountain Lodge

Callahan's Mountain Lodge
3.0 star property
Ashland
8.8 out of 10, Excellent, (1168)
"Beautiful place to stay "
United States
Daniel
The price is NT$3,238
NT$3,760 total
includes taxes & fees
Jan 19 - 2026/1/20
Callahan's Mountain Lodge

Rogue Regency Inn Medford Airport

Rogue Regency Inn Medford Airport
3.0 star property
Medford
8.8 out of 10, Excellent, (2714)
"I really enjoyed this Hotel and stay."
United States
Okesa
The price is NT$2,699
NT$3,036 total
includes taxes & fees
Jan 11 - 2026/1/12
Rogue Regency Inn Medford Airport

Wine Country Inn

Wine Country Inn
3.0 star property
Jacksonville
9.4 out of 10, Exceptional, (1001)
"Very friendly staff. Clean and comfortable. Only complaint is the walls are very thin. Loved this cute little town! "
United States
Jody
The price is NT$3,380
NT$3,735 total
includes taxes & fees
Jan 1 - 2026/1/2
Wine Country Inn

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

Lady Geneva Bed and Breakfast

Lady Geneva Bed and Breakfast
3.5 star property
City Center Medford
10.0 out of 10, Exceptional, (71)
"This bnb was so charming and the couple that runs and owns it is lovely. They make a wonderful breakfast and the rooms are gorgeous. Historic building at it's finest. "
United States
Maria
The price is NT$5,479
NT$6,164 total
includes taxes & fees
Dec 26 - Dec 27
Lady Geneva Bed and Breakfast

Lanka Rose House by WanderLodges

Lanka Rose House by WanderLodges
3.5 star property
Phoenix
10.0 out of 10, Exceptional, (2)
"Very cute house with all the necessities for a cozy stay. "
United States
Roxanne
The price is NT$3,502
NT$8,142 total
includes taxes & fees
Dec 30 - Dec 31
Lanka Rose House by WanderLodges

Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (7)
"Great ~ memorable stay. "
United States
Melissa
The price is NT$3,920
NT$8,559 total
includes taxes & fees
Jan 22 - 2026/1/23
Barclay Klum House by WanderLodges
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 Historic Downtown District Hotel Reviews

Explore a world of travel with Expedia