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Featured Healdsburg Romantic Getaways & Hotels

Grape Leaf Inn

Grape Leaf Inn

4 out of 5
539 Johnson Street Healdsburg CA
$219 nightly
The price is $254 total per night
$254 total
Dec 14 - Dec 15
Total with taxes and fees
With a stay at Grape Leaf Inn in Healdsburg, you'll be within a 10-minute walk of Raven Performing Arts Theater and Healdsburg Center for the Arts.
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location

Modern Wine Country Cottage in Historic Healdsburg, Premiere Location

Healdsburg CA
When you stay at this vacation home in Healdsburg, you'll be on a river, within a 10-minute walk of SingleThread Farm at Dry Creek and Dry Creek Vineyard.
Healdsburg Inn on the Plaza, A Four Sisters Inn

Healdsburg Inn on the Plaza, A Four Sisters Inn

3.5 out of 5
112 Matheson Healdsburg CA
$177 nightly
The price is $206 total per night
$206 total
Dec 23 - Dec 24
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
A stay at Healdsburg Inn on the Plaza, A Four Sisters Inn places you in the heart of Healdsburg, steps from Healdsburg Plaza and a 5-minute drive from Wilson Winery.
Breakfast included
Free WiFi
Calderwood Inn

Calderwood Inn

3.5 out of 5
25 West Grant Street Healdsburg CA
$181 nightly
The price is $210 total per night
$210 total
Dec 14 - Dec 15
Total with taxes and fees
With a stay at Calderwood Inn in Healdsburg, you'll be within a 10-minute walk of Seghesio Family Vineyards and Raven Performing Arts Theater.
27 North

27 North

4 out of 5
27 North St Healdsburg CA
$740 nightly
The price is $860 total per night
$860 total
Dec 14 - Dec 15
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
A stay at 27 North places you in the heart of Healdsburg, steps from Raven Performing Arts Theater and 3 minutes by foot from Healdsburg Plaza.
Large Outdoor Kitchen, Pool, Hot Tub, Firepit...8 Mins From Healdsburg Plaza

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

Healdsburg CA
Located in Healdsburg, this vacation home is on a river, within a 5-minute drive of Medlock Ames Winery and Starlite Vineyards.
Duchamp Healdsburg

Duchamp Healdsburg

3.5 out of 5
421 Foss St Healdsburg CA
A stay at Duchamp Healdsburg places you in the heart of Healdsburg, within a 5-minute drive of Healdsburg Plaza and Russian River.
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard

True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard

Forestville CA
$440 nightly
The price is $495 total per night
$495 total
Dec 14 - Dec 15
Total with taxes and fees
With a stay at this cottage, you'll be centrally located in Healdsburg, within a 10-minute drive of Porter Creek Vineyards and Russian River.
Hotel Healdsburg

Hotel Healdsburg

4 out of 5
25 Matheson St Healdsburg CA
$444 nightly
The price is $516 total per night
$516 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
Hotel Healdsburg is centrally located in Healdsburg, a 2-minute walk from Healdsburg Plaza and 15 minutes by foot from Russian River.
Rockhouse Suites

Rockhouse Suites

3 out of 5
115 Mill Street Healdsburg CA
Rockhouse Suites is in the heart of Healdsburg, within a 5-minute walk of Healdsburg Plaza and Healdsburg Center for the Arts.
Best Western Dry Creek Inn

Best Western Dry Creek Inn

3 out of 5
198 Dry Creek Rd Healdsburg CA
$144 nightly
The price is $167 total per night
$167 total
Dec 14 - Dec 15
Total with taxes and fees
Located in Healdsburg, Dry Creek Inn MOD Collection by Sonesta is in the suburbs, within a 5-minute drive of Healdsburg Plaza and Trentadue Winery.
H2Hotel

H2Hotel

4 out of 5
219 Healdsburg Ave Healdsburg CA
$266 nightly
The price is $309 total per night
$309 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
H2Hotel is centrally located in Healdsburg, a 3-minute walk from Healdsburg Plaza and 5 minutes by foot from Healdsburg Museum.
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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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Healdsburg hotels essential information

Accommodation
494 hotels
Lowest Price
$167
Highest Price
$860
Popular hotels
Grape Leaf Inn, Modern Wine Country Cottage in Historic Healdsburg, Premiere Location, Healdsburg Inn on the Plaza, A Four Sisters Inn, Calderwood Inn, 27 North, Large Outdoor Kitchen, Pool, Hot Tub, Firepit...8 Mins From Healdsburg Plaza, Duchamp Healdsburg, True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard, Hotel Healdsburg, Rockhouse Suites, Best Western Dry Creek Inn, H2Hotel

Most Recent Healdsburg Hotel Reviews

Appellation Healdsburg

Appellation Healdsburg

5 out of 5
Posted 7 days ago
CheapTickets Verified Review
"Amazing! Room was clean and staff friendly and responsive!"
A verified traveler stayed at Appellation Healdsburg
Appellation Healdsburg

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