Search Cottages in Healdsburg

  • 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
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Healdsburg cottages

Exterior detail

Farm Country Cottage in Downtown Geyserville, Vineyard Views + UNTI Wine

Farm Country Cottage in Downtown Geyserville, Vineyard Views + UNTI Wine
Geyserville
10.0 out of 10, Exceptional, (2 reviews)
"Cozy, rustic, and with all great amenities."
United States
Gina I.
The price is AED 716
AED 1,361 total
includes taxes & fees
20 May - 21 May
Farm Country Cottage in Downtown Geyserville, Vineyard Views + UNTI Wine
Exterior

Backyard Garden Oasis

Backyard Garden Oasis
3.0 star property
Middletown
9.6 out of 10, Exceptional, (51 reviews)
"Cute garden area, quiet, nice all inclusive spot"
United States
Jodi
The price is AED 768
AED 856 total
includes taxes & fees
7 May - 8 May
Backyard Garden Oasis
Outdoor dining

Garden house with gas fireplace

Garden house with gas fireplace
Middletown
10.0 out of 10, Exceptional, (1 review)
"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.
The price is AED 375
AED 830 total
includes taxes & fees
12 May - 13 May
Garden house with gas fireplace
Exterior

Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Calistoga
10.0 out of 10, Exceptional, (3 reviews)
"Yes, our little buddy was welcome!"
United States
Doug G.
The price is AED 951
AED 1,300 total
includes taxes & fees
11 May - 12 May
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Smart TV, fireplace

Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.6 out of 10, Exceptional, (73 reviews)
"We stayed for a girls weekend for a napa get away. and we brought the dog and it was a great stay. And clean too. Easy for a home base. And it was affordable. Would stay again "
United States
Valerie C.
The price is AED 698
AED 1,487 total
includes taxes & fees
10 May - 11 May
Wine Country Cottage in downtown Santa Rosa, CA
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
Dillon Beach
10.0 out of 10, Exceptional, (73 reviews)
"The property was wonderful. The Sundog cottage is adorable with all the amenities needed for a great stay with kids and pets. As an added bonus the property is close to the beach which is just a short walk away and the beach is dog friendly. "
United States
Gabriella W.
The price is AED 988
AED 2,069 total
includes taxes & fees
7 May - 8 May
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
Exterior

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, (39 reviews)
"Perfect little cottage within walking distance to everything in downtown Calistoga! Bed was so comfy and the fireplace made it feel extra cozy. We definitely want to stay here again!"
United States
Cameron D.
The price is AED 1,062
AED 1,450 total
includes taxes & fees
11 May - 12 May
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
House (2 Bedrooms) | Interior

Watefront Getaway w/ Mtn Views & Dock in Clearlake

Watefront Getaway w/ Mtn Views & Dock in Clearlake
3.0 star property
Clearlake
The price is AED 529
AED 991 total
includes taxes & fees
7 May - 8 May
Watefront Getaway w/ Mtn Views & Dock in Clearlake
Terrace/patio

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 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
The price is AED 1,025
AED 1,405 total
includes taxes & fees
13 May - 14 May
Escape to wine country in your independent cottage in downtown Calistoga
Exterior

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 AED 1,649
AED 2,121 total
includes taxes & fees
15 May - 16 May
Charming King Cottage
Dining

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 AED 657
AED 830 total
includes taxes & fees
13 May - 14 May
Comfort and Style in Our Queen Cottage
Outdoor dining

Relaxing Beekeeper's Cottage with hot tub

Relaxing Beekeeper's Cottage with hot tub
Bodega Bay
10.0 out of 10, Exceptional, (22 reviews)
"A Lovely tucked away Cottage, with relaxing amenities, close to everything Bodega Bay has to offer"
United States
Brian K.
The price is AED 786
AED 1,718 total
includes taxes & fees
7 May - 8 May
Relaxing Beekeeper's Cottage with hot tub
Outdoor spa tub

The Carriage House Sonoma • Hot Tub • Vineyard Views • Complimentary Bottle

The Carriage House Sonoma • Hot Tub • Vineyard Views • Complimentary Bottle
Kenwood
9.0 out of 10, Wonderful, (2 reviews)
"Such a cute place! The turn into the property is a bit hidden right before the bridge but once you find it the house is so secluded with plenty of space. The kitchen was fully stocked and had everything you could think of. Did a wine tasting with their tasting room and everyone was so welcoming and sweet. Thank you! "
United States
Sara W.
The price is AED 1,833
AED 2,288 total
includes taxes & fees
10 May - 11 May
The Carriage House Sonoma • Hot Tub • Vineyard Views • Complimentary Bottle
Terrace/patio

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, (3 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 AED 551
AED 1,146 total
includes taxes & fees
2 Jun - 3 Jun
Modern Farmhouse on Vineyard w/ Deck, Bocce & Wine Country Views
Terrace/patio

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 AED 1,025
AED 1,760 total
includes taxes & fees
11 May - 12 May
Stunning Sauna Cottage Retreat on Private Vineyard
Terrace/patio

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 AED 940
AED 1,057 total
includes taxes & fees
11 May - 12 May
Antique Indonesian Teakwood Cottage for a Romantic Getaway in Petaluma, California
Microwave, oven, stovetop, dishwasher

Enchanting Vineyard cottage nestled in the wine country!

Enchanting Vineyard cottage nestled in the wine country!
Santa Rosa
The price is AED 1,451
AED 2,760 total
includes taxes & fees
11 May - 12 May
Enchanting Vineyard cottage nestled in the wine country!
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

Harmon Guest House

Harmon Guest House

10/10 Excellent
"Excellent location with modern rooms. The only negative was that the bed was way too soft for us, but for a 3 day weekend we could tolerate it. I loved that the hotel had refillable water containers which creates less waste. Staff were very nice. Breakfast is very basic but plenty of great restaurants within walking distance. Would definitely come back! "
Linda 3-night trip
Posted 6 hours ago
Harmon Guest House

Frequently asked questions

How much do cottages in Healdsburg cost?
Prepare to pay between AED 830 and AED 2,760 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 19 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.
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.