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

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Healdsburg cottages

A modern building with a metal exterior, a wooden door, and a small window on the side.

1. Country Carriage House in Downtown Geyserville, Vineyard Views

Country Carriage House in Downtown Geyserville, Vineyard Views
Geyserville
10.0 out of 10, Exceptional, (5 reviews)
"Cozy, rustic, and with all great amenities."
United States
Gina I.
The price is AU$551
includes taxes & fees
22 Oct - 23 Oct
Country Carriage House in Downtown Geyserville, Vineyard Views
A wooden deck with wicker furniture and a metal table, overlooking a vineyard and hills.

2. Garden house with gas fireplace

Garden house with gas fireplace
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"It was a quaint country house. The host was attentive, but also left us to ourselves. The house was clean. A/C worked well. It was very comfortable."
United States
Amy
The price is AU$294
includes taxes & fees
22 Oct - 23 Oct
Garden house with gas fireplace
A small, single-story house with a front porch, a chimney, and a door with a window above it.

3. Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Calistoga
9.6 out of 10, Exceptional, (47 reviews)
"We stayed here 15 years ago , same bedspreads and no new updates . We love it for its cozy feeling , and love the peacefulness of staying in Calistoga. We walked across the street for an awesome dinner at Sam’s Social club , walked down the street to shop and cruise around this quaint town . It’s a high price point , but we always enjoy our time there . I worry that if they ever remodel this place , the price point will be more than what it’s worth a night , for which I don’t believe would be...
United States
William
The price is AU$679
includes taxes & fees
21 Oct - 22 Oct
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
A small, single-story house with a front porch, a chimney, and a door with a window above it.

4. Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Calistoga
10.0 out of 10, Exceptional, (5 reviews)
"Property is beautiful rooms are so clean. Service was incredible."
United States
Paul L.
The price is AU$668
includes taxes & fees
21 Oct - 22 Oct
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
A building with a sign that reads "Russian River Brewing Company."

5. Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (82 reviews)
"Lovely vacation rental"
United States
suzanne g.
The price is AU$647
includes taxes & fees
27 Oct - 28 Oct
Wine Country Cottage in downtown Santa Rosa, CA
A hot tub with a blue light, surrounded by a wooden fence and string lights.

6. Hot tub lake wine Cottage State Park 4 mins away

Hot tub lake wine Cottage State Park 4 mins away
Kelseyville
10.0 out of 10, Exceptional, (3 reviews)
"10/10 stay!"
United States
Janneth M.
The price is AU$366
includes taxes & fees
22 Oct - 23 Oct
Hot tub lake wine Cottage State Park 4 mins away
A house with a porch, a wooden door, and two rocking chairs. There are two suitcases and a table with bottles on the porch.

7. Escape to wine country in your independent cottage in downtown Calistoga

Escape to wine country in your independent cottage in downtown Calistoga
Calistoga
9.8 out of 10, Exceptional, (8 reviews)
"We absolutely loved our stay! The home was clean, quiet, private, and incredibly convenient. We were especially grateful that the hosts allowed our three dogs, which made this trip extra special. We spent a few days enjoying Calistoga and Napa before taking our sweet pup to UC Davis, and this was the perfect place for us. As empty nesters, we love traveling with our three dogs and hope to stay here again someday!"
United States
Jennifer G.
The price is AU$679
includes taxes & fees
21 Oct - 22 Oct
Escape to wine country in your independent cottage in downtown Calistoga
A cabin with a wooden deck, a balcony, and a staircase leading to a door.

8. Hillside Retreat in the Redwoods | Hot Tub

Hillside Retreat in the Redwoods | Hot Tub
Guerneville
10.0 out of 10, Exceptional, (5 reviews)
"Great place! Nice and cozy!"
United States
John B.
The price is AU$795
includes taxes & fees
22 Oct - 23 Oct
Hillside Retreat in the Redwoods | Hot Tub
A deck with a sofa, a glass-top coffee table, and a view of a hilly landscape.

9. Dog-friendly Haven w/ Stunning Views in Bodega Bay

Dog-friendly Haven w/ Stunning Views in Bodega Bay
3.0 star property
Bodega Bay
The price is AU$1,392
includes taxes & fees
18 Nov - 19 Nov
Dog-friendly Haven w/ Stunning Views in Bodega Bay
A two-story house with a wooden deck and a covered front porch.

10. Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog

Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
Dillon Beach
10.0 out of 10, Exceptional, (85 reviews)
"Lovely spot for a getaway!"
United States
Lisa M.
The price is AU$795
includes taxes & fees
25 Oct - 26 Oct
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
A wooden deck with a stone pathway leading to a hammock.

11. Stunning Sauna Cottage Retreat on Private Vineyard

Stunning Sauna Cottage Retreat on Private Vineyard
Sebastopol
10.0 out of 10, Exceptional, (3 reviews)
"Nice area in the vineyards. Sauna was great. Place was clean. "
United States
Cesar R.
The price is AU$681
includes taxes & fees
27 Oct - 28 Oct
Stunning Sauna Cottage Retreat on Private Vineyard
A wooden deck with a red umbrella, a wooden chair, and a table.

12. Relaxing Beekeeper's Cottage with hot tub

Relaxing Beekeeper's Cottage with hot tub
Bodega Bay
10.0 out of 10, Exceptional, (22 reviews)
"The cottage was charming, clean and well appointed. "
United States
Edie H.
The price is AU$833
includes taxes & fees
27 Oct - 28 Oct
Relaxing Beekeeper's Cottage with hot tub
Outdoor dining

13. Antique Indonesian Teakwood Cottage for a Romantic Getaway in Petaluma, California

Antique Indonesian Teakwood Cottage for a Romantic Getaway in Petaluma, California
Petaluma
The price is AU$476
includes taxes & fees
29 Oct - 30 Oct
Antique Indonesian Teakwood Cottage for a Romantic Getaway in Petaluma, California
A two-story house with a covered porch, a stone pathway, and a well-maintained garden with various shrubs and trees.

14. The Atlas Calistoga - Cottage #1

The Atlas Calistoga - Cottage #1
Calistoga
10.0 out of 10, Exceptional, (19 reviews)
"Great space, impeccably appointed, amazing location. Would stay again. "
United States
Kris R.
The price is AU$850
includes taxes & fees
21 Oct - 22 Oct
The Atlas Calistoga - Cottage #1
A wooden pathway leading to a house with a view of a lake and mountains.

15. Watefront Getaway w/ Mtn Views & Dock in Clearlake

Watefront Getaway w/ Mtn Views & Dock in Clearlake
3.0 star property
Clearlake
4.0 out of 10, (1 review)
"If it weren’t for the kindness of the host, who accommodated us for an early check-in and late checkout, I would’ve given this zero stars. It’s totally rundown, looks like it hasn’t been power washed in 20 years, as soon as you walk up it smells like mold. The listing doesn’t tell you that it’s on a main street. The inside has rotting walls with actual holes, you can smell the mold and in one of the bedrooms it smelled so toxic like cat urine and chemicals - no one could sleep in there. The...
United States
Jennifer
The price is AU$392
includes taxes & fees
3 Nov - 4 Nov
Watefront Getaway w/ Mtn Views & Dock in Clearlake
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 Healdsburg Hotel Reviews

The Madrona

The Madrona

10/10 Excellent
"We had a great stay and loved the Madrona. We'll be back!"
Leslie 1-night trip
Posted 11 hours ago
The Madrona

Find out more about Healdsburg

Healdsburg Cottages information

Number of reviews
279
Accommodation
15 Cottages
Lowest Price
AU$294
Highest Price
AU$1,392

Frequently asked questions

How much do cottages in Healdsburg cost?
Prices for cottages in Healdsburg range between AU$294 and AU$1,392 per night. No matter your budget, you'll find a perfect place to relax and reconnect with nature. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Healdsburg?
Pack your suitcase and choose from 15 cottages in Healdsburg. Thinking about a place where you can get reacquainted with nature? Expedia can help you find the ideal property in just a few clicks.
What is there to do in Healdsburg near my cottage?
You'll find tons of terrific things to fill your days in Healdsburg. Explore well-known attractions like Francis Ford Coppola Winery, Armstrong Redwoods State Park and Dry Creek Vineyard. Kendall-Jackson Wine Estate and Gardens, Trentadue Winery and Mazzocco Winery are also visitor favourites.