Healdsburg Guest Houses

A garden pathway lined with white roses leading to a building with a stone facade and a window.

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Our top choices for Healdsburg guest houses

A table set with a cheese board, wine glasses, and bottles, with a green sofa and lush greenery in the background.

1. Calderwood Inn

Healdsburg

Tom

includes taxes & fees

9 Nov - 10 Nov

A lush green landscape with a variety of trees and a grassy area.

2. Guerneville Lodge

Guerneville

Shannon

includes taxes & fees

5 Nov - 6 Nov

A bedroom with a bed, a desk, a chair, a TV, a window, and a balcony.

3. Love Shack private retreat

Middletown

Gretchen F.

includes taxes & fees

15 Oct - 16 Oct

A bedroom with a large bed, a bedside table with a lamp and a plant, and a window with curtains.

4. Central Santa Rosa Getaway w/ Private Outdoor Space

Santa Rosa

Vance C.

includes taxes & fees

8 Nov - 9 Nov

A loft bedroom with a bunk bed, a bedside table with a lamp, a TV, and a window with a view.

5. The Well House with outdoor seating and loft!

Middletown

louis s.

A garden pathway leading to a building with a white picket fence and hanging purple flowers.

6. Glen Ellen Inn

Glen Ellen

lorraine

includes taxes & fees

8 Nov - 9 Nov

A house with a tower-like structure, surrounded by a garden with a stone path and a wooden bridge.

7. Okaeri Calistoga

Calistoga

Stacy

includes taxes & fees

19 Oct - 20 Oct

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Top Healdsburg Hotel Reviews

Dry Creek Inn MOD Collection by Sonesta

10/10 Excellent

"The room was very clean and comfortable. A little odd to find the mini fridge and coffee in the bathroom area, but it worked. Make sure the doors shut tight as we had someone walk in. I would prefer if the sliding door to the bathroom sink area wasn’t frosted glass so others could sleep and not be disturbed. Overall tho I would for sure stay here again! Very comfortable and good location. Also a joining rooms for our party was fabulous!"

Harmon Guest House

8/10 Good

"The Founder’s suite was enormous and wonderfully laid out. The two showers and the soaking tub were amazing. Unfortunately, the amenities and staff fell short. The complementary breakfast was very basic and we had to wait awhile for them to replenish many of the items. We also had to ask for utensils. Sometimes the request at breakfast was met nicely, sometimes the staff was dismissive. The front desk couldn’t find bath salts for the soaking tub. The front desk also seemed an overwhelmed at times and we ended up grabbing our own dolly for our luggage."

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