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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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.
$335 nightly
The price is $373
Oct 22 - Oct 23
Total with taxes and fees
Country Carriage House in Downtown Geyserville, Vineyard Views
yard view of old growth stump, stairs to front door, gate from off-parking

2. Pumpkin House Summary

Pumpkin House Summary
Guerneville
10.0 out of 10, Exceptional, (13 reviews)
"Nice place, quiet. Loved the hot tub. "
United States
Nathan B.
$352 nightly
The price is $376
Sep 30 - Oct 1
Total with taxes and fees
Pumpkin House Summary
A wooden deck with wicker furniture and a metal table, overlooking a vineyard and hills.

3. 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
$198 nightly
The price is $198
Oct 1 - Oct 2
Total with taxes and fees
Garden house with gas fireplace
A wooden deck with a round table and two chairs, surrounded by a white railing.

4. Comfort and Style in Our Queen Cottage

Comfort and Style in Our Queen Cottage
Calistoga
9.8 out of 10, Exceptional, (49 reviews)
"Great place to stay. Clean and well appointed and in a great location for access to sites, vineyards, and restaurants "
United States
Robert
$226 nightly
The price is $256
Sep 30 - Oct 1
Total with taxes and fees
Comfort and Style in Our Queen Cottage
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, (79 reviews)
"Lovely vacation rental"
United States
suzanne g.
$374 nightly
The price is $398
Oct 7 - Oct 8
Total with taxes and fees
Wine Country Cottage in downtown Santa Rosa, CA
A small, single-story house with a front porch, a chimney, and a door with a window above it.

6. 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, (45 reviews)
"Host, amenities, location….all excellent. "
United States
Amy B.
$388 nightly
The price is $465
Sep 30 - Oct 1
Total with taxes and fees
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.

7. 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.
$331 nightly
The price is $401
Oct 5 - Oct 6
Total with taxes and fees
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
A hot tub with a blue light, surrounded by a wooden fence and string lights.

8. 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.
$205 nightly
The price is $221
Sep 30 - Oct 1
Total with taxes and fees
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.

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

Escape to wine country in your independent cottage in downtown Calistoga
Calistoga
10.0 out of 10, Exceptional, (6 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.
$334 nightly
The price is $404
Oct 5 - Oct 6
Total with taxes and fees
Escape to wine country in your independent cottage in downtown Calistoga
A small, single-story house with a porch, a red door, and two bicycles parked outside.

10. Charming King Cottage

Charming King Cottage
Calistoga
9.8 out of 10, Exceptional, (11 reviews)
"Nice comfortable cottage."
United States
Michael E. S.
$269 nightly
The price is $306
Oct 12 - Oct 13
Total with taxes and fees
Charming King Cottage
A wooden pathway leading to a house with a view of a lake and mountains.

11. 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
$245 nightly
The price is $274
Oct 4 - Oct 5
Total with taxes and fees
Watefront Getaway w/ Mtn Views & Dock in Clearlake
A two-story house with a wooden deck and a covered front porch.

12. 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, (84 reviews)
"Lovely spot for a getaway!"
United States
Lisa M.
$508 nightly
The price is $570
Sep 30 - Oct 1
Total with taxes and fees
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
A wooden deck with a stone pathway leading to a hammock.

13. 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.
$442 nightly
The price is $492
Oct 19 - Oct 20
Total with taxes and fees
Stunning Sauna Cottage Retreat on Private Vineyard
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 Atlas Calistoga - Cottage #1
A wooden deck with a red umbrella, a wooden chair, and a table.

15. 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.
$440 nightly
The price is $498
Oct 27 - Oct 28
Total with taxes and fees
Relaxing Beekeeper's Cottage with hot tub
Outdoor spa tub

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

Antique Indonesian Teakwood Cottage for a Romantic Getaway in Petaluma, California
Petaluma
$302 nightly
The price is $302
Oct 1 - Oct 2
Total with taxes and fees
Antique Indonesian Teakwood Cottage for a Romantic Getaway in Petaluma, California
A deck with a sofa, a glass-top coffee table, and a view of a hilly landscape.

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

Dog-friendly Haven w/ Stunning Views in Bodega Bay
3.0 star property
Bodega Bay
$945 nightly
The price is $1,077
Oct 2 - Oct 3
Total with taxes and fees
Dog-friendly Haven w/ Stunning Views in Bodega Bay
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

Hotel Trio Healdsburg

Hotel Trio Healdsburg

10/10 Excellent
"Great place and love the van to downtown"
Linda 1-night trip
Posted 13 hours ago
Hotel Trio Healdsburg

Find out more about Healdsburg

Healdsburg Cottages information

Number of reviews
333
Accommodation
16 Cottages
Lowest Price
$198
Highest Price
$1,077

Frequently asked questions

How much do cottages in Healdsburg cost?
Prepare to pay between $198 and $1,077 per night for cottages in Healdsburg. Whatever your budget, an awesome stay is just a click or two away on Expedia. These prices were 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?
Lock in your vacation dates and then choose from 16 cottages in Healdsburg. Looking for a place where you can relax and stay in touch with nature? Expedia will help you find your ideal retreat in a few quick clicks.
Are there any family-friendly cottages in Healdsburg?
Check in to Wine Country Getaway Modern Three and make your family vacation to Healdsburg a memorable one. This family-friendly cottage has a 3-star rating and amenities such as WiFi and a firepit. Once you've checked in and unpacked your things, there's no shortage of family-friendly attractions to discover in and around Healdsburg. Healdsburg Museum and Pacific Coast Air Museum are two of our top suggestions.
Why book your cottage in Healdsburg with Expedia?
We think that a vacay should be a walk in the park, so if you're on the lookout for cottages in Healdsburg at a competitive rate, Expedia has you covered. Save those pennies and select an economical option far from the rush of the city, or splurge on a 5-star cottage to spoil your favorite people.
How can I find cheap cottages in Healdsburg?
Expedia can help you easily source cheap cottages in Healdsburg. To find your dream stay in a couple of clicks, simply use our convenient filter tool to refine your search results by budget, amenities and star rating.
What is there to do in Healdsburg near my cottage?
Whatever you're interested in, Healdsburg has lots of things to keep you busy. Healdsburg Golf Club, Pezzi King Winery and Soda Rock Winery are on many visitors' sightseeing itineraries. Don't forget to explore Wilson Winery, Matrix Winery and Healdsburg Plaza either. With Expedia's Healdsburg hotel deals, you can see more awesome attractions like these with the money you save.

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