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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 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 €357
includes taxes & fees
22 Oct - 23 Oct
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 €342
includes taxes & fees
18 Oct - 19 Oct
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 €186
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.

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, (46 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 €430
includes taxes & fees
20 Oct - 21 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.

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 €430
includes taxes & fees
19 Oct - 20 Oct
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
A cabin with a wooden deck, a balcony, and a staircase leading to a door.

6. 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 €455
includes taxes & fees
18 Oct - 19 Oct
Hillside Retreat in the Redwoods | Hot Tub
A building with a sign that reads "Russian River Brewing Company."

7. 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 €415
includes taxes & fees
15 Nov - 16 Nov
Wine Country Cottage in downtown Santa Rosa, CA
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.
The price is €235
includes taxes & fees
18 Oct - 19 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.

9. 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 €430
includes taxes & fees
19 Oct - 20 Oct
Escape to wine country in your independent cottage in downtown Calistoga
A wooden pathway leading to a house with a view of a lake and mountains.

10. 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 €244
includes taxes & fees
18 Oct - 19 Oct
Watefront Getaway w/ Mtn Views & Dock in Clearlake
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 €438
includes taxes & fees
19 Oct - 20 Oct
Stunning Sauna Cottage Retreat on Private Vineyard
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, (85 reviews)
"Lovely spot for a getaway!"
United States
Lisa M.
The price is €550
includes taxes & fees
28 Oct - 29 Oct
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
A modern, open-plan living space with a large sliding door, a sofa set, and a dining area with a table and benches.

13. 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.
Modern Farmhouse on Vineyard w/ Deck, Bocce & Wine Country Views
A wooden deck with a red umbrella, a wooden chair, and a table.

14. 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 €531
includes taxes & fees
27 Oct - 28 Oct
Relaxing Beekeeper's Cottage with hot tub
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 €304
includes taxes & fees
16 Nov - 17 Nov
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 #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 €580
includes taxes & fees
21 Oct - 22 Oct
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

Calderwood Inn

Calderwood Inn

10/10 Excellent
"Calderwood Inn was a very nice Bed and breakfast I would highly recommend, our room was very spacious and breakfast was quite delicious. The property had a nice porch and a lovely garden and with several sitting areas to enjoy the our door and a glass of wine if you like. The hotel was located within a 5 minute walk to town. We thouroghly enjoyed our stay at this quaint little bed and breakfast."
Janet 3-night trip
Posted 12 hours ago
Calderwood Inn

Find out more about Healdsburg

Healdsburg Cottages information

Number of reviews
297
Accommodation
15 Cottages
Lowest Price
€235
Highest Price
€580

Frequently asked questions

How much do cottages in Healdsburg cost?
Prepare to pay between €235 and €580 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 holiday 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 holiday 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 holiday 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 favourite 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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