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In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Healdsburg cottages

Property grounds
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard

True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard

True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Forestville
10.0 out of 10, Exceptional, (11)
"Ideal for a relaxing time in wine country! The winery on property is fantastic and highly recommend it!"
United States
Paul H.
$440 nightly
The price is $495
Dec 21 - Dec 22
Total with taxes and fees
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Exterior
Backyard Garden Oasis

Backyard Garden Oasis

Backyard Garden Oasis
3.0 star property
Middletown
9.6 out of 10, Exceptional, (51)
"Cute garden area, quiet, nice all inclusive spot"
United States
Jodi
$209 nightly
The price is $233
Dec 21 - Dec 22
Total with taxes and fees
Backyard Garden Oasis
Outdoor dining
Garden house with gas fireplace

Garden house with gas fireplace

Garden house with gas fireplace
Middletown
10.0 out of 10, Exceptional, (1)
"We were not originally planning on staying in Middletown but were pleasantly surprised on arrival. The Garden House is very comfortable and convenient to many things in town. Linda, our host had special little touches that made the stay relaxing. Number one the shower is amazing! I looked forward to it every evening the pressure and hot water is perfect and the quality shampoos and soaps provides smelled wonderful! The kitchen is well stocked if you are cooking during your stay. And there is...
United States
kelsie i.
$231 nightly
The price is $254
Dec 22 - Dec 23
Total with taxes and fees
Garden house with gas fireplace
Property grounds
Comfort and Style in Our Queen Cottage

Comfort and Style in Our Queen Cottage

Comfort and Style in Our Queen Cottage
Calistoga
9.8 out of 10, Exceptional, (49)
"The cottage was very well appointed, very clean and comfortable. we really enjoyed our 2 night stay!Communication, check in and out were a breeze!Thank you!!"
United States
Kevin T.
$359 nightly
The price is $430
Jan 11 - Jan 12, 2026
Total with taxes and fees
Comfort and Style in Our Queen Cottage
Exterior
Escape to Wine Country in your independant Cottage in Downtown Calistoga

Escape to Wine Country in your independant Cottage in Downtown Calistoga

Escape to Wine Country in your independant Cottage in Downtown Calistoga
Calistoga
10.0 out of 10, Exceptional, (2)
"Loved everything Ellen was very accommodating ,pleasant and polite As well as professional The furnishings were very up scale and same style as my home One suggestion The tv should be more accessible so it does not block AC when pulled out from the wall I’m not being critical because I love this place. I will stay there every time I would ever be close to Calistoga. AND I adore Ellen personally and professionally!!👍❤️"
United States
Ronny
$305 nightly
The price is $366
Dec 22 - Dec 23
Total with taxes and fees
Escape to Wine Country in your independant Cottage in Downtown Calistoga
Terrace/patio
Escape to wine country in your independent cottage in downtown Calistoga

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, (3)
"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
$308 nightly
The price is $369
Dec 22 - Dec 23
Total with taxes and fees
Escape to wine country in your independent cottage in downtown Calistoga
House (2 Bedrooms) | Interior
Watefront Getaway w/ Mtn Views & Dock in Clearlake

Watefront Getaway w/ Mtn Views & Dock in Clearlake

Watefront Getaway w/ Mtn Views & Dock in Clearlake
3.0 star property
Clearlake
$209 nightly
The price is $230
Jan 1 - Jan 2, 2026
Total with taxes and fees
Watefront Getaway w/ Mtn Views & Dock in Clearlake
Exterior
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

Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
Dillon Beach
10.0 out of 10, Exceptional, (59)
"This cottage was so cute! So close to the beach, super comfortable beds, and Valerie was an awesome host! This is a must stay if you are looking for a place in Dillon beach "
United States
Lauren S.
$546 nightly
The price is $613
Jan 4 - Jan 5, 2026
Total with taxes and fees
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
Exterior
Charming King Cottage

Charming King Cottage

Charming King Cottage
Calistoga
9.8 out of 10, Exceptional, (11)
"This property was amazing!! Very clean, comfortable and exactly as described in the listing. Our host reached out personally to make sure we had the check in instructions. When we come back to Calistoga we will stay here again!!"
United States
Rich S.
$382 nightly
The price is $458
Jan 11 - Jan 12, 2026
Total with taxes and fees
Charming King Cottage
Exterior
Escape to Wine County in your independant Cottage in Downtown Calistoga

Escape to Wine County in your independant Cottage in Downtown Calistoga

Escape to Wine County in your independant Cottage in Downtown Calistoga
Calistoga
9.6 out of 10, Exceptional, (30)
"Great place! Clean, and very close to everything!"
United States
Levi J.
$305 nightly
The price is $368
Jan 4 - Jan 5, 2026
Total with taxes and fees
Escape to Wine County in your independant Cottage in Downtown Calistoga
Exterior
Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (62)
"Tim and Caroline’s cottage was perfect for our two night stay. We loved how close it was to the shops and restaurants in downtown Santa Rosa. Definitely recommend."
United States
Adam R.
$368 nightly
The price is $389
Jan 2 - Jan 3, 2026
Total with taxes and fees
Wine Country Cottage in downtown Santa Rosa, CA
Outdoor dining
Relaxing Beekeeper's Cottage with hot tub

Relaxing Beekeeper's Cottage with hot tub

Relaxing Beekeeper's Cottage with hot tub
Bodega Bay
10.0 out of 10, Exceptional, (21)
"A Lovely tucked away Cottage, with relaxing amenities, close to everything Bodega Bay has to offer"
United States
Brian K.
$623 nightly
The price is $699
Dec 25 - Dec 26
Total with taxes and fees
Relaxing Beekeeper's Cottage with hot tub
Terrace/patio
Stunning Sauna Cottage Retreat on Private Vineyard

Stunning Sauna Cottage Retreat on Private Vineyard

Stunning Sauna Cottage Retreat on Private Vineyard
Sebastopol
10.0 out of 10, Exceptional, (3)
"Nice area in the vineyards. Sauna was great. Place was clean. "
United States
Cesar R.
$471 nightly
The price is $521
Dec 26 - Dec 27
Total with taxes and fees
Stunning Sauna Cottage Retreat on Private Vineyard
Terrace/patio
Modern Farmhouse on Vineyard w/ Deck, Bocce & Wine Country Views

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

Modern Farmhouse on Vineyard w/ Deck, Bocce & Wine Country Views
Sonoma
$257 nightly
The price is $284
Jan 19 - Jan 20, 2026
Total with taxes and fees
Modern Farmhouse on Vineyard w/ Deck, Bocce & Wine Country Views
Outdoor dining
Antique Indonesian Teakwood Cottage for a Romantic Getaway in Petaluma, California

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

Antique Indonesian Teakwood Cottage for a Romantic Getaway in Petaluma, California
2.0 star property
Petaluma
$291 nightly
The price is $291
Jan 1 - Jan 2, 2026
Total with taxes and fees
Antique Indonesian Teakwood Cottage for a Romantic Getaway in Petaluma, California
Interior
Russian River Retreat! Woodsy Guerneville Bungalow

Russian River Retreat! Woodsy Guerneville Bungalow

Russian River Retreat! Woodsy Guerneville Bungalow
3.0 star property
Guerneville
$394 nightly
The price is $445
Dec 22 - Dec 23
Total with taxes and fees
Russian River Retreat! Woodsy Guerneville Bungalow
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 Vinea, a Travelodge by Wyndham

Hotel Vinea, a Travelodge by Wyndham

10/10 Excellent
"♡"
Chloe 1-night trip
Posted 2 days ago
Hotel Vinea, a Travelodge by Wyndham

Find out more about Healdsburg

Healdsburg Cottages information

Number of reviews
292
Accommodation
17 Cottages
Lowest Price
$230
Highest Price
$699

Frequently asked questions

How much do cottages in Healdsburg cost?
Prepare to pay between $230 and $699 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 17 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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