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Dec 19 - Dec 20
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Dec 20 - Dec 21
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Dec 19 - Dec 21
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Dec 26 - Dec 28

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Our top choices for Simi Winery hotels

Aerial view
Montage Healdsburg

Montage Healdsburg

Montage Healdsburg
5.0 star property
1.7 km from Simi Winery
9.6 out of 10, Exceptional, (117)
"Clean room, kind and helpful staff. Nice ambiance in vineyard. "
United States
Arthur
The price is ￥108,235
￥137,242 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Montage Healdsburg
Business center
The Ruse

The Ruse

The Ruse
5.0 star property
2.7 km from Simi Winery
9.6 out of 10, Exceptional, (106)
"Our room was spacious and furnishings were attractive, beds were comfortable. Breakfast and coffee service was lovely."
United States
Alice
The price is ￥36,870
￥42,841 total
includes taxes & fees
Dec 23 - Dec 24
The Ruse
Lobby
27 North

27 North

27 North
4.0 star property
3.1 km from Simi Winery
9.6 out of 10, Exceptional, (302)
"Overall a very nice hotel centrally located. "
United States
Laurence
The price is ￥94,140
￥115,714 total
includes taxes & fees
Dec 23 - Dec 24
27 North
Front of property - evening/night
Hotel Trio Healdsburg

Hotel Trio Healdsburg

Hotel Trio Healdsburg
3.0 star property
1.6 km from Simi Winery
9.4 out of 10, Exceptional, (870)
"Quiet, clean, spacious rooms with full kitchens. Nice lobby and wine bar. Outdoor fire pits and bbqs. Will stay again"
United States
Joe
The price is ￥23,651
￥30,737 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hotel Trio Healdsburg
Exterior
Cottages at Little Saint

Cottages at Little Saint

Cottages at Little Saint
4.0 star property
3.1 km from Simi Winery
9.4 out of 10, Exceptional, (68)
"It was very easy to check in and our cottage was very comfortable. "
United States
Glenn
Cottages at Little Saint
Terrace/patio
The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton
3.5 star property
1.7 km from Simi Winery
9.0 out of 10, Wonderful, (399)
"Great staff "
United States
Poonam
The price is ￥24,726
￥28,730 total
includes taxes & fees
Jan 19 - Jan 20, 2026
The Lodge at Healdsburg, Tapestry Collection by Hilton
Exterior
Calderwood Inn

Calderwood Inn

Calderwood Inn
3.5 star property
2.7 km from Simi Winery
9.0 out of 10, Wonderful, (250)
"House and room were cute, and main part of the house was decorated for the holidays. Walkable distance to the main Square and bike/walking path on same block to town. Excellent breakfast in the morning. It was nice to go to Healdsburg during the off-season And this was definitely a nice place to stay."
United States
Carol
The price is ￥24,718
￥28,673 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Calderwood Inn
Seasonal outdoor pool, open 8:30 AM to 9:00 PM, sun loungers
Camellia Inn

Camellia Inn

Camellia Inn
3.5 star property
3.1 km from Simi Winery
8.4 out of 10, Very Good, (601)
"The staff was so so wonderful and helpful with recommendations and reservations! This place was so cute and close to all the downtown shops and restaurants! "
United States
Mckenna
The price is ￥26,572
￥30,825 total
includes taxes & fees
Dec 21 - Dec 22
Camellia Inn
Suite (Wine Country) | In-room safe, desk, laptop workspace, blackout drapes
Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta
3.0 star property
1.7 km from Simi Winery
8.0 out of 10, Very Good, (1003)
"Clean room, staff was very friendly and checking in was easy"
United States
Benjamin
The price is ￥20,228
￥23,504 total
includes taxes & fees
Dec 28 - Dec 29
Dry Creek Inn MOD Collection by Sonesta
Gazebo
Hotel Vinea, a Travelodge by Wyndham

Hotel Vinea, a Travelodge by Wyndham

Hotel Vinea, a Travelodge by Wyndham
2.5 star property
1.6 km from Simi Winery
7.4 out of 10, Good, (711)
"I love this hotel. Great location. It’s quiet. Love the suite with the jetted tub. Staff is all very kind. "
United States
Stacey
The price is ￥15,965
￥18,519 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Hotel Vinea, a Travelodge by Wyndham
Meeting facility
Appellation Healdsburg

Appellation Healdsburg

Appellation Healdsburg
4.5 star property
0.7 km from Simi Winery
9.0 out of 10, Wonderful, (34)
"Beautiful resort!! "
United States
Jennifer
The price is ￥41,999
￥59,648 total
includes taxes & fees
Dec 21 - Dec 22
Appellation Healdsburg
Exterior
The Madrona

The Madrona

The Madrona
4.0 star property
4.1 km from Simi Winery
9.6 out of 10, Exceptional, (42)
"Love the Madrona. Absolutely beautiful property with the cutest rooms & delicious dining. "
United States
Katie
The price is ￥69,934
￥86,397 total
includes taxes & fees
Dec 23 - Dec 24
The Madrona
Outdoor pool, sun loungers
H2Hotel

H2Hotel

H2Hotel
4.0 star property
3.5 km from Simi Winery
9.4 out of 10, Exceptional, (706)
"The room was beautiful and so clean. Loved the location "
United States
arleen
The price is ￥35,954
￥48,102 total
includes taxes & fees
Jan 19 - Jan 20, 2026
H2Hotel
BBQ/picnic area
Harmon Guest House

Harmon Guest House

Harmon Guest House
3.0 star property
3.5 km from Simi Winery
9.4 out of 10, Exceptional, (438)
"Nice rooms, great location. Team needs some basic service training as they tend to make simple situations difficult citing their “system” and “policy” limitations. They create frustration for the customer where it is easily avoided. "
United States
Sarah
The price is ￥43,412
￥56,771 total
includes taxes & fees
Dec 21 - Dec 22
Harmon Guest House
Property grounds
Cottages on River Road

Cottages on River Road

Cottages on River Road
2.5 star property
16.8 km from Simi Winery
9.6 out of 10, Exceptional, (1000)
"Fantastic, beautiful place at a reasonable price. Great included breakfast and super friendly staff.. Will definitely return here when in the area "
United States
Carlos
Cottages on River Road
Restaurant
The Stavrand Russian River Valley

The Stavrand Russian River Valley

The Stavrand Russian River Valley
4.0 star property
18.6 km from Simi Winery
9.6 out of 10, Exceptional, (61)
"Clean, beautiful property. The staff was super friendly and helpful. Best turn down service I’ve ever experienced. Thank you!! "
United States
Heather
The price is ￥55,091
￥62,804 total
includes taxes & fees
Dec 21 - Dec 22
The Stavrand Russian River Valley
Free daily continental breakfast
Hotel Healdsburg

Hotel Healdsburg

Hotel Healdsburg
4.0 star property
3.4 km from Simi Winery
9.2 out of 10, Wonderful, (431)
"Lovely hotel in the heart of Healdsburg. Wonderful stay. "
United States
Erica
The price is ￥50,469
￥66,779 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hotel Healdsburg
Deluxe Double Queen Room | In-room safe, iron/ironing board, cribs/infant beds, rollaway beds
Geyserville Inn

Geyserville Inn

Geyserville Inn
3.5 star property
8.9 km from Simi Winery
9.2 out of 10, Wonderful, (1000)
"Friendly staff and clean comfortable rooms. We enjoyed the breakfast at the restaurant next door. "
United States
Jill
The price is ￥19,792
￥24,691 total
includes taxes & fees
Dec 20 - Dec 21
Geyserville Inn
Exterior
Vinarosa Resort & Spa

Vinarosa Resort & Spa

Vinarosa Resort & Spa
4.0 star property
18.8 km from Simi Winery
9.4 out of 10, Exceptional, (805)
"Amazing place"
United States
Robert
The price is ￥36,119
￥50,272 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Vinarosa Resort & Spa
Fireplace
AutoCamp Sonoma

AutoCamp Sonoma

AutoCamp Sonoma
3.5 star property
19.9 km from Simi Winery
9.4 out of 10, Exceptional, (143)
"Friendly staff, clean and current facilities. Fun for the family. Nice, quiet location for food and playing in the woods."
United States
brandee
The price is ￥22,282
￥31,665 total
includes taxes & fees
Jan 4 - Jan 5, 2026
AutoCamp Sonoma
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 Simi Winery Hotel Reviews

Hotel Trio Healdsburg

Hotel Trio Healdsburg

10/10 Excellent
"Quiet, clean, spacious rooms with full kitchens. Nice lobby and wine bar. Outdoor fire pits and bbqs. Will stay again"
Joe 2-night trip
Posted 5 days ago
Hotel Trio Healdsburg

Hotels near other Simi Winery attractions

Healdsburg Ridge Open Space Preserve

Explore the great outdoors at Healdsburg Ridge Open Space Preserve, a lovely green space in Healdsburg. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.
See properties

Krug Event Center

Krug Event Center is just one of the places to see in Healdsburg, so why not enjoy the other things to explore during your travels? Stroll along the riverfront in this family-friendly area, or check out its wineries.
See properties

Frequently asked questions

What's the area like around Simi Winery?
Simi Winery is located in a welcoming area of Healdsburg known for its selection of wineries and array of dining options. If you're looking for a convenient place to stay, check out the 18 hotels and other accommodations you'll find within a mile.
What's the best place to stay near Simi Winery?
Appellation Healdsburg is one of the top choices for your stay based on our traveler data, and this hotel offers 2 outdoor pools and a full-service spa. It's located just a short 0.5 mi (0.7 km) from Simi Winery. Another good option is Hotel Trio Healdsburg, located just 1 mi (1.6 km) away.
How many hotels can I expect to find near Simi Winery?
Expedia has 18 hotels and other accommodations within a mile from Simi Winery.
If I need to cancel the hotel reservation for my stay near Simi Winery, will I receive a refund?
Yes! You'll find that most room reservations are fully refundable if cancelled prior to the hotel's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If your reservation is non-refundable, you might be able to cancel it and get a refund within 24 hours of booking. Enter your dates, click on "Search", then use the "fully refundable" filter to get the best deals available near Simi Winery.
Where can I learn more about changing or cancelling my trip in the area near Simi Winery?
For additional details about picking new dates or cancelling your stay near Simi Winery, click here.
What can I see and do near Simi Winery?
Attractions like Raven Performing Arts Theater and Healdsburg Museum highlight the local culture. If you have some time to wander around the area, you might stop by Mazzocco Winery, Jordan Vineyard & Winery, or Francis Ford Coppola Winery. Healdsburg Plaza and SingleThread Farm at Dry Creek are some sights worth a visit in the area.