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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Healdsburg cottages

Exterior detail

1. Country Carriage House in Downtown Geyserville, Vineyard Views

Country Carriage House in Downtown Geyserville, Vineyard Views
Geyserville
10.0 out of 10, Exceptional, (4 reviews)
"Cozy, rustic, and with all great amenities."
United States
Gina I.
The price is CA $225
CA $538 total
includes taxes & fees
Oct 8 - Oct 9
Country Carriage House in Downtown Geyserville, Vineyard Views
Outdoor dining

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 CA $135
CA $279 total
includes taxes & fees
Sep 13 - Sep 14
Garden house with gas fireplace
Exterior

3. 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.
The price is CA $290
CA $595 total
includes taxes & fees
Sep 22 - Sep 23
Wine Country Cottage in downtown Santa Rosa, CA
Property grounds

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
The price is CA $302
CA $391 total
includes taxes & fees
Sep 20 - Sep 21
Comfort and Style in Our Queen Cottage
Exterior

5. 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.
Hillside Retreat in the Redwoods | Hot Tub
Terrace/patio

6. 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 made the Calistoga CA area our base for our recent trip and the Cottage Grove Inn served as a great place to stay."
United States
Anonymous traveller
The price is CA $426
CA $584 total
includes taxes & fees
Sep 13 - Sep 14
Escape to wine country in your independent cottage in downtown Calistoga
Exterior

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

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Calistoga
9.8 out of 10, Exceptional, (44 reviews)
"Host, amenities, location….all excellent. "
United States
Amy B.
The price is CA $467
CA $641 total
includes taxes & fees
Sep 15 - Sep 16
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Exterior

8. Charming King Cottage

Charming King Cottage
Calistoga
9.8 out of 10, Exceptional, (11 reviews)
"Nice comfortable cottage."
United States
Michael E. S.
The price is CA $329
CA $426 total
includes taxes & fees
Sep 20 - Sep 21
Charming King Cottage
Terrace/patio

9. 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 CA $428
CA $723 total
includes taxes & fees
Sep 22 - Sep 23
Stunning Sauna Cottage Retreat on Private Vineyard
Exterior

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

Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Calistoga
10.0 out of 10, Exceptional, (4 reviews)
"Property is beautiful rooms are so clean. Service was incredible."
United States
Paul L.
The price is CA $426
CA $584 total
includes taxes & fees
Oct 6 - Oct 7
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Outdoor spa tub

11. 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, (2 reviews)
"10/10 stay!"
United States
Janneth M.
The price is CA $186
CA $308 total
includes taxes & fees
Sep 21 - Sep 22
Hot tub lake wine Cottage State Park 4 mins away
House (2 Bedrooms) | Interior

12. 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 CA $237
CA $378 total
includes taxes & fees
Sep 13 - Sep 14
Watefront Getaway w/ Mtn Views & Dock in Clearlake
Exterior

13. 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, (83 reviews)
"Lovely spot for a getaway!"
United States
Lisa M.
The price is CA $371
CA $780 total
includes taxes & fees
Sep 14 - Sep 15
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
Room

14. The Atlas Calistoga - Cottage #2

The Atlas Calistoga - Cottage #2
Calistoga
10.0 out of 10, Exceptional, (24 reviews)
"Perfect stay, walking distance to Calistoga town which had restaurants and groceries. Apartment was super clean and cozy, had everything we needed. The host was very responsive with any questions we had, and also extremely accommodating. Would stay here again next time in the Calistoga. "
United States
Samantha L.
The price is CA $572
CA $906 total
includes taxes & fees
Sep 20 - Sep 21
The Atlas Calistoga - Cottage #2
Outdoor dining

15. 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 CA $369
CA $419 total
includes taxes & fees
Sep 27 - Sep 28
Antique Indonesian Teakwood Cottage for a Romantic Getaway in Petaluma, California
Exterior

16. The Atlas Calistoga - Cottage #1

The Atlas Calistoga - Cottage #1
Calistoga
10.0 out of 10, Exceptional, (17 reviews)
"Great space, impeccably appointed, amazing location. Would stay again. "
United States
Kris R.
The price is CA $635
CA $992 total
includes taxes & fees
Sep 20 - Sep 21
The Atlas Calistoga - Cottage #1
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 Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton

10/10 Excellent
"This is the second time I’ve stayed here and I will definitely stay again the next time I’m back in Healdsburg. The location is really good it’s a lovely small walk on a path to downtown. It’s super clean and the beds are very comfortable. The rooms have cute little patios too! And it’s a dog friendly place. Highly recommend!"
Rebecca 1-night trip
Posted 23 hours ago
The Lodge at Healdsburg, Tapestry Collection by Hilton

Find out more about Healdsburg

Healdsburg Cottages information

Number of reviews
284
Accommodation
16 Cottages
Lowest Price
CA $279
Highest Price
CA $992

Frequently asked questions

How much do cottages in Healdsburg cost?
Prepare to pay between CA $279 and CA $992 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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