Search Luxury Hotels in Healdsburg

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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Healdsburg Luxury Hotels

Tonight
31 Dec - 1 Jan
Tomorrow
1 Jan - 2 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Healdsburg luxury hotels

Gazebo
Hotel Vinea, a Travelodge by Wyndham

Hotel Vinea, a Travelodge by Wyndham

Hotel Vinea, a Travelodge by Wyndham
2.5 star property
Healdsburg
7.4 out of 10, Good, (715)
"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 Rp1.750.892
Rp2.031.034 total
includes taxes & fees
23 Jan - 24 Jan 2026
Hotel Vinea, a Travelodge by Wyndham
Front of property
Healdsburg Inn on the Plaza, A Four Sisters Inn

Healdsburg Inn on the Plaza, A Four Sisters Inn

Healdsburg Inn on the Plaza, A Four Sisters Inn
3.5 star property
Healdsburg
8.6 out of 10, Excellent, (566)
"Clean room, nice people, Janine was very helpful in answering our questions. "
United States
Paul
Healdsburg Inn on the Plaza, A Four Sisters Inn
Outdoor pool, open 9:00 AM to 9 PM, pool umbrellas, pool loungers
Fairview Inn and Suites

Fairview Inn and Suites

Fairview Inn and Suites
3.0 star property
Healdsburg
7.8 out of 10, Good, (1002)
"Rooms are always clean and well maintained and staff are always friendly."
United States
Nicholas
The price is Rp1.982.634
Rp2.299.855 total
includes taxes & fees
4 Jan - 5 Jan 2026
Fairview Inn and Suites
Suite, 1 King Bed, Non Smoking, Fireplace (with Sofabed) | Living area | 55-inch flat-screen TV with cable channels, TV
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
Healdsburg
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 Rp1.696.387
Rp1.971.096 total
includes taxes & fees
14 Jan - 15 Jan 2026
Dry Creek Inn MOD Collection by Sonesta
Outdoor pool, pool loungers
H2Hotel

H2Hotel

H2Hotel
4.0 star property
Healdsburg
9.4 out of 10, Exceptional, (707)
"The room was beautiful and so clean. Loved the location "
United States
arleen
The price is Rp3.877.455
Rp5.187.486 total
includes taxes & fees
29 Jan - 30 Jan 2026
H2Hotel
Lobby
27 North

27 North

27 North
4.0 star property
Healdsburg
9.6 out of 10, Exceptional, (302)
"Overall a very nice hotel centrally located. "
United States
Laurence
The price is Rp8.888.127
Rp11.009.658 total
includes taxes & fees
4 Jan - 5 Jan 2026
27 North
Exterior
The Madrona

The Madrona

The Madrona
4.0 star property
Healdsburg
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 Rp7.836.250
Rp9.653.052 total
includes taxes & fees
19 Jan - 20 Jan 2026
The Madrona
Exterior
Hotel Healdsburg

Hotel Healdsburg

Hotel Healdsburg
4.0 star property
Healdsburg
9.2 out of 10, Wonderful, (431)
"Lovely hotel in the heart of Healdsburg. Wonderful stay. "
United States
Erica
The price is Rp6.022.466
Rp7.874.760 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hotel Healdsburg
Executive Room, 1 King Bed | Terrace/patio
Calderwood Inn

Calderwood Inn

Calderwood Inn
3.5 star property
Healdsburg
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 Rp2.665.750
Rp3.092.237 total
includes taxes & fees
19 Jan - 20 Jan 2026
Calderwood 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.
View all properties

Top Healdsburg Hotel Reviews

Hotel Vinea, a Travelodge by Wyndham

Hotel Vinea, a Travelodge by Wyndham

10/10 Excellent
"♡"
Chloe 1-night trip
Posted 13 days ago
Hotel Vinea, a Travelodge by Wyndham
Best Western Dry Creek Inn

Best Western Dry Creek Inn

10/10 Excellent
"conveniently located, room and staff exceeded expectations"
Julianne 2-night trip
Posted 2 weeks ago
Best Western Dry Creek Inn

Frequently asked questions

Are you searching for a great accommodation for your luxury trip to Healdsburg?
During your visit, you might want to enjoy the wineries and shopping which Healdsburg is known for.
What's the best luxury hotel in Healdsburg?
Appellation Healdsburg is a luxury hotel with a full-service spa and 2 outdoor pools, and it's a popular choice for Expedia travellers looking for an elegant place to stay. Montage Healdsburg and 27 North are other upscale choices for your stay.
When can I expect good weather in Healdsburg?
Planning for the weather is an important factor for making your trip to Healdsburg a success, especially when you're splurging. The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are December and January, with an average of 9°C. Average annual precipitation for Healdsburg is 777 mm.
What's there to see and do in Healdsburg?
Experience all that Healdsburg has to offer when you visit Healdsburg Plaza, Jordan Vineyard & Winery and SingleThread Farm at Dry Creek. If you have a little extra time during your trip, you might want to check out Dry Creek Vineyard and Russian River.