Find Romantic Hotels in Healdsburg, CA

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Check availability on Healdsburg Romantic Hotels

Compare Healdsburg Romantic Hotels room rates, reviews, and availability. Most hotels are fully refundable.

Grape Leaf Inn
Garden

Grape Leaf Inn

4.0 star property
9.4 out of 10, Exceptional, (153)
"A cute, vintage b&b near the square! Such nice hosts, and a delicious breakfast! "
The price is SAR 755
SAR 876 total
includes taxes & fees
17 Feb - 18 Feb
Grape Leaf Inn
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
First Crush Cottage

Modern Wine Country Cottage in Historic Healdsburg, Premiere Location

10.0 out of 10, Exceptional, (154)
"My family and I stayed here for the Thanksgiving holiday and had an absolutely wonderful stay. The place is well equipped and very cozy with a wood burning fireplace, beautiful outdoor spaces (including multiple fire pits) and comfortable bedrooms. The host is also amazing - communication before, during and after was easy and included fantastic recommendations. And to top it all off, they even treated my family and I to a complimentary tasting at a local winery. Would definitely recommend!"
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
Healdsburg Inn on the Plaza, A Four Sisters Inn
Room

Healdsburg Inn on the Plaza, A Four Sisters Inn

3.5 star property
8.4 out of 10, Very Good, (547)
"Nice breakfast. View of the square. Easy access. "
The price is SAR 1,037
SAR 1,205 total
includes taxes & fees
18 Feb - 19 Feb
Healdsburg Inn on the Plaza, A Four Sisters Inn
Calderwood Inn
Front of property

Calderwood Inn

3.5 star property
9.2 out of 10, Wonderful, (226)
"We stayed at The Calderwood Inn Valentines week 2025. It is a beautiful, well kept B&B. The people were wonderful and the breakfasts were very tasty. Walking distance to the Healdsburg square and less than 10 minutes to the Dry Creek Valley. We will definitely stay there again! "
The price is SAR 508
SAR 589 total
includes taxes & fees
17 Mar - 18 Mar
Calderwood Inn
Hotel Les Mars
Front of property

Hotel Les Mars

4.0 star property
9.6 out of 10, Exceptional, (280)
"Wonder hotel - great location and walking distance to shops and restaurants! "
The price is SAR 1,778
SAR 2,218 total
includes taxes & fees
23 Feb - 24 Feb
Hotel Les Mars
Large Outdoor Kitchen, Pool, Hot Tub, Firepit...8 Mins From Healdsburg Plaza
Your own private resort with large pool, hot tub, outdoor kitchen and vineyard

Large Outdoor Kitchen, Pool, Hot Tub, Firepit...8 Mins From Healdsburg Plaza

10.0 out of 10, Exceptional, (112)
"Amazing property. From the pool to the jacuzzi, outdoor seating, string lights and outdoor kitchen like no other, we couldn't have asked for more. Inside was farmhouse chic. Extremely comfortable beds and accommodations. Charming nooks and crannies everywhere. I could go on and on but have to mention the stunning waterfalls. Michael was very responsive to any and all questions and he has really thought of everything to make renter's stay fabulous. The only downside -- it was hard to cook...
Large Outdoor Kitchen, Pool, Hot Tub, Firepit...8 Mins From Healdsburg Plaza
Duchamp Hotel Private Suites
Outdoor pool

Duchamp Hotel Private Suites

3.5 star property
9.2 out of 10, Wonderful, (87)
"The property offers great privacy as it is bungalows around a pool. Each room is spacious and comfortable. Short walking distance to all the must stop spots in Healdsburg."
Duchamp Hotel Private Suites
Milk barn Magic: Vineyard Escape with 2 Bedrooms
Cozy bedroom featuring a comfortable queen bed, abundant natural sunlight.

Milk barn Magic: Vineyard Escape with 2 Bedrooms

10.0 out of 10, Exceptional, (11)
"Ideal for a relaxing time in wine country! The winery on property is fantastic and highly recommend it!"
The price is SAR 675
SAR 1,727 total
includes taxes & fees
4 Mar - 5 Mar
Milk barn Magic: Vineyard Escape with 2 Bedrooms
Hotel Healdsburg
Lobby lounge

Hotel Healdsburg

4.0 star property
9.2 out of 10, Wonderful, (386)
"Front desk very accommodating, had pack n play set up. Room was somewhat spartan, sparkling tap water did not work, no breakfast (unlike booking straight through hotel), no black out shades. Overall a nice stay. "
The price is SAR 1,448
SAR 1,683 total
includes taxes & fees
17 Feb - 18 Feb
Hotel Healdsburg
Rockhouse Suites
Room

Rockhouse Suites

3.0 star property
9.4 out of 10, Exceptional, (20)
"Very comfortable suite "
Rockhouse Suites
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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Frequently asked questions

Searching for romantic hotels in Healdsburg?
Are you in need of a romantic escape? Couples choose Healdsburg for its array of wineries, top-notch restaurants, and stunning river views. If you want to spend a romantic day sharing a bottle of wine with your love, you might plan a visit to Seghesio Family Vineyards, Simi Winery, or Matrix Winery. Whether you want to sip a glass of champagne or enjoy a candlelit dinner, there are 2 hotels and other accommodations in Healdsburg.
How many romantic hotels should we expect to find in Healdsburg?
Expedia has 10 romantic Healdsburg hotels for you both to enjoy.
When is the best time of year for a romantic getaway to Healdsburg?
If you’re hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Healdsburg: The hottest months are usually July and August with an average temp of 69°F, while the coldest months are December and January with an average of 49°F. Average annual precipitation for Healdsburg is 31 inches.
What is there to do in Healdsburg?
There’s nothing better than wandering around a new destination with your sweetheart, so consider checking out all that Healdsburg has to offer. If you’re hoping to see some of the area’s cultural attractions, you and your partner will love Healdsburg for its array of wineries and major shopping area. If you want to spend a day exploring, you might consider a stop at Healdsburg Plaza, Jordan Vineyard & Winery, or Dry Creek Vineyard.
What's the best way to get to Healdsburg and around town during my romantic getaway?
This information about transportation options in Healdsburg might help your romantic trip go off without a hitch: To get to Healdsburg, book a flight to Santa Rosa, CA (STS-Sonoma County), which is the closest major airport, located 7.7 mi (12.5 km) from the city center. If you’d like to venture out around the area, you may want to rent a car for your trip.