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

Search Healdsburg Cottage Rentals from CA $281

  • 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 prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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 CA $228
CA $548 total
includes taxes & fees
Oct 29 - Oct 30
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.
The price is CA $259
CA $528 total
includes taxes & fees
Oct 28 - Oct 29
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
The price is CA $137
CA $281 total
includes taxes & fees
Oct 29 - Oct 30
Garden house with gas fireplace
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, Pet Friendly, and Walkable to Downtown

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Calistoga
9.6 out of 10, Exceptional, (48 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 CA $461
CA $632 total
includes taxes & fees
Oct 27 - Oct 28
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.

5. 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 CA $419
CA $574 total
includes taxes & fees
Oct 27 - Oct 28
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
A building with a sign that reads "Russian River Brewing Company."

6. 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)
"Our stay was pleasant, the place was exceptionally clean and the owners were very helpful."
United States
joanne h.
The price is CA $322
CA $644 total
includes taxes & fees
Nov 2 - Nov 3
Wine Country Cottage in downtown Santa Rosa, CA
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 CA $419
CA $574 total
includes taxes & fees
Oct 27 - Oct 28
Escape to wine country in your independent cottage in downtown Calistoga
A wooden pathway leading to a treehouse with a wooden deck and a staircase.

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 CA $545
CA $949 total
includes taxes & fees
Nov 12 - Nov 13
Hillside Retreat in the Redwoods | Hot Tub
A hot tub with a blue light, surrounded by a wooden fence and string lights.

9. 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, (5 reviews)
"10/10 stay!"
United States
Janneth M.
The price is CA $168
CA $359 total
includes taxes & fees
Oct 28 - Oct 29
Hot tub lake wine Cottage State Park 4 mins away
A deck with a sofa, a glass-top coffee table, and a view of a hilly landscape.

10. 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 CA $588
CA $1,354 total
includes taxes & fees
Nov 5 - Nov 6
Dog-friendly Haven w/ Stunning Views in Bodega Bay
A two-story house with a wooden deck and a covered front porch.

11. 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 CA $377
CA $794 total
includes taxes & fees
Oct 29 - Oct 30
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
A wooden deck with a stone pathway leading to a hammock.

12. 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 $391
CA $676 total
includes taxes & fees
Oct 27 - Oct 28
Stunning Sauna Cottage Retreat on Private Vineyard
A wooden deck with a red umbrella, a wooden chair, and a table.

13. 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 CA $447
CA $884 total
includes taxes & fees
Nov 16 - Nov 17
Relaxing Beekeeper's Cottage with hot tub
A modern, open-plan living space with a large sliding door, a sofa set, and a dining area with a table and benches.

14. Modern Farmhouse on Vineyard w/ Deck, Bocce & Wine Country Views

Modern Farmhouse on Vineyard w/ Deck, Bocce & Wine Country Views
Sonoma
10.0 out of 10, Exceptional, (6 reviews)
"Had a wonderful stay, right next to a vinyard. Area was nice and quiet. Would definitely recommend. "
United States
David B.
The price is CA $319
CA $577 total
includes taxes & fees
Oct 27 - Oct 28
Modern Farmhouse on Vineyard w/ Deck, Bocce & Wine Country Views
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 $375
CA $472 total
includes taxes & fees
Oct 29 - Oct 30
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.

16. The Atlas Calistoga - Cottage #3

The Atlas Calistoga - Cottage #3
Calistoga
10.0 out of 10, Exceptional, (22 reviews)
"Great cottage within walking distance to downtown Calistoga."
United States
Joel S.
The price is CA $648
CA $1,011 total
includes taxes & fees
Oct 31 - Nov 1
The Atlas Calistoga - Cottage #3
A wooden pathway leading to a house with a view of a lake and mountains.

17. 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 $241
CA $383 total
includes taxes & fees
Oct 27 - Oct 28
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Healdsburg Hotel Reviews

The Madrona

The Madrona

8/10 Good
"Lovely property, will beautiful views of the surrounding area."
Alexandra 1-night trip
Posted 4 hours ago
The Madrona

Find out more about Healdsburg

Healdsburg Cottages information

Number of reviews
307
Accommodation
15 Cottages
Lowest Price
CA $281
Highest Price
CA $1,354

Frequently asked questions

How much do cottages in Healdsburg cost?
Prepare to pay between CA $281 and CA $1,354 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 15 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.

Explore a world of travel with Expedia