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 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

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, (5 reviews)
"Cozy, rustic, and with all great amenities."
United States
Gina I.
$353 nightly
The price is $391
Oct 8 - Oct 9
Total with taxes and fees
Country Carriage House in Downtown Geyserville, Vineyard Views
Property grounds

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.
$336 nightly
The price is $360
Sep 22 - Sep 23
Total with taxes and fees
Pumpkin House Summary
Outdoor dining

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
$201 nightly
The price is $201
Sep 27 - Sep 28
Total with taxes and fees
Garden house with gas fireplace
Exterior

4. 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.
$395 nightly
The price is $419
Sep 20 - Sep 21
Total with taxes and fees
Wine Country Cottage in downtown Santa Rosa, CA
Exterior

5. 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.
$367 nightly
The price is $444
Sep 21 - Sep 22
Total with taxes and fees
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Property grounds

6. 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
$247 nightly
The price is $280
Sep 20 - Sep 21
Total with taxes and fees
Comfort and Style in Our Queen Cottage
Exterior

7. Charming King Cottage

Charming King Cottage
Calistoga
9.8 out of 10, Exceptional, (11 reviews)
"Nice comfortable cottage."
United States
Michael E. S.
$270 nightly
The price is $306
Sep 20 - Sep 21
Total with taxes and fees
Charming King Cottage
Exterior

8. 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.
$353 nightly
The price is $423
Oct 5 - Oct 6
Total with taxes and fees
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Outdoor spa tub

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, (2 reviews)
"10/10 stay!"
United States
Janneth M.
$209 nightly
The price is $225
Sep 22 - Sep 23
Total with taxes and fees
Hot tub lake wine Cottage State Park 4 mins away
Terrace/patio

10. 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 traveler
$353 nightly
The price is $423
Oct 5 - Oct 6
Total with taxes and fees
Escape to wine country in your independent cottage in downtown Calistoga
Terrace/patio

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.
$433 nightly
The price is $479
Sep 22 - Sep 23
Total with taxes and fees
Stunning Sauna Cottage Retreat on Private Vineyard
Property grounds

12. Ocean view, Huge backyard, 5 minutes walk to the beach

Ocean view, Huge backyard, 5 minutes walk to the beach
Bodega Bay
9.0 out of 10, Wonderful, (2 reviews)
"So nice and quite "
United States
Amber B.
$439 nightly
The price is $496
Sep 21 - Sep 22
Total with taxes and fees
Ocean view, Huge backyard, 5 minutes walk to the beach
House (2 Bedrooms) | Interior

13. 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
Sep 21 - Sep 22
Total with taxes and fees
Watefront Getaway w/ Mtn Views & Dock in Clearlake
Exterior

14. Sebastopol Retreat w/ Pool, Hot Tub, Fire Pit, Entertainment Barn, Orchard & BBQ

Sebastopol Retreat w/ Pool, Hot Tub, Fire Pit, Entertainment Barn, Orchard & BBQ
Sebastopol
10.0 out of 10, Exceptional, (2 reviews)
"We needed a place to relax and reconnect with family. This home is perfect for a small family or two couples to hang out. It has everything you need to make coffee, cook food and has plenty of space to spread out. Loved the backyard with hot tub. We did not use the pool given the weather but the hot tub was perfect. Plus, the backyard was ideal to let our son's dog get out and chase a frisbee. Overall, fantastic experience plus, communication with Ehab was easy and responsive."
United States
Robert K.
$1,022 nightly
The price is $1,117
Sep 30 - Oct 1
Total with taxes and fees
Sebastopol Retreat w/ Pool, Hot Tub, Fire Pit, Entertainment Barn, Orchard & BBQ
Exterior

15. 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.
$554 nightly
The price is $623
Sep 20 - Sep 21
Total with taxes and fees
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
Iron/ironing board, travel crib, WiFi, bed sheets

16. 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.
$545 nightly
The price is $617
Sep 20 - Sep 21
Total with taxes and fees
The Atlas Calistoga - Cottage #2
Terrace/patio

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

Antique Indonesian Teakwood Cottage for a Romantic Getaway in Petaluma, California
Petaluma
$291 nightly
The price is $291
Sep 25 - Sep 26
Total with taxes and fees
Antique Indonesian Teakwood Cottage for a Romantic Getaway in Petaluma, California
Exterior

18. The Atlas Calistoga - Cottage #1

The Atlas Calistoga - Cottage #1
Calistoga
10.0 out of 10, Exceptional, (18 reviews)
"Great space, impeccably appointed, amazing location. Would stay again. "
United States
Kris R.
$599 nightly
The price is $678
Sep 20 - Sep 21
Total with taxes and fees
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

Hotel Trio Healdsburg

Hotel Trio Healdsburg

10/10 Excellent
"Absolutely wonderful. The breakfast was superb a you eat on real china with silverware."
Mark 1-night trip
Posted 1 hour ago
Hotel Trio Healdsburg

Find out more about Healdsburg

Healdsburg Cottages information

Number of reviews
297
Accommodation
16 Cottages
Lowest Price
$201
Highest Price
$1,117

Frequently asked questions

How much do cottages in Healdsburg cost?
Prepare to pay between $201 and $1,117 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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