Search Healdsburg Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
apart-hotel image
Aparthotels
Aparthotels

Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

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.
$340 nightly
The price is $378
Dec 3 - Dec 4
Total with taxes and fees
Country Carriage House in Downtown Geyserville, Vineyard Views
A small, single-story house with a front porch, a chimney, and a door with a window above it.

2. 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, (49 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
$292 nightly
The price is $353
Nov 19 - Nov 20
Total with taxes and fees
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
yard view of old growth stump, stairs to front door, gate from off-parking

3. Pumpkin House Summary

Pumpkin House Summary
Guerneville
10.0 out of 10, Exceptional, (14 reviews)
"Nice place, quiet. Loved the hot tub. "
United States
Nathan B.
$335 nightly
The price is $359
Nov 15 - Nov 16
Total with taxes and fees
Pumpkin House Summary
A wooden deck with wicker furniture and a metal table, overlooking a vineyard and hills.

4. 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
$192 nightly
The price is $192
Nov 15 - Nov 16
Total with taxes and fees
Garden house with gas fireplace
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.
$292 nightly
The price is $353
Nov 16 - Nov 17
Total with taxes and fees
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, (83 reviews)
"Our stay was pleasant, the place was exceptionally clean and the owners were very helpful."
United States
joanne h.
$389 nightly
The price is $414
Nov 15 - Nov 16
Total with taxes and fees
Wine Country Cottage in downtown Santa Rosa, CA
A wooden pathway leading to a treehouse with a wooden deck and a staircase.

7. 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.
$539 nightly
The price is $598
Nov 19 - Nov 20
Total with taxes and fees
Hillside Retreat in the Redwoods | Hot Tub
A house with a porch, a wooden door, and two rocking chairs. There are two suitcases and a table with bottles on the porch.

8. 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)
"Such a great property. Idyllic, clean and lovely interior. Nice area for breakfast and coffee, loved the bikes! Very friendly staff. Will return."
United States
Douglas F.
$292 nightly
The price is $353
Nov 19 - Nov 20
Total with taxes and fees
Escape to wine country in your independent cottage in downtown Calistoga
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
9.8 out of 10, Exceptional, (7 reviews)
"10/10 stay!"
United States
Janneth M.
$239 nightly
The price is $265
Nov 15 - Nov 16
Total with taxes and fees
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
$848 nightly
The price is $967
Nov 18 - Nov 19
Total with taxes and fees
Dog-friendly Haven w/ Stunning Views in Bodega Bay
A wooden deck with a view of a large tree, a fenced yard, and a distant body of water.

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

Ocean view, Huge backyard, 5 minutes walk to the beach
Bodega Bay
9.6 out of 10, Exceptional, (5 reviews)
"So nice and quite "
United States
Amber B.
$492 nightly
The price is $556
Nov 15 - Nov 16
Total with taxes and fees
Ocean view, Huge backyard, 5 minutes walk to the beach
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.
$415 nightly
The price is $461
Nov 15 - Nov 16
Total with taxes and fees
Stunning Sauna Cottage Retreat on Private Vineyard
A two-story house with a wooden deck and a covered front porch.

13. 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, (86 reviews)
"The place is very cute and cozy. A nice little walk to the beach. The bed was incredible! The price for 1 night was a little crazy, but otherwise it was lovely."
United States
Katie M.
$495 nightly
The price is $559
Nov 16 - Nov 17
Total with taxes and fees
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
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, (23 reviews)
"The cottage was charming, clean and well appointed. "
United States
Edie H.
$532 nightly
The price is $604
Nov 16 - Nov 17
Total with taxes and fees
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.

15. 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, (7 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
Outdoor dining

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

Antique Indonesian Teakwood Cottage for a Romantic Getaway in Petaluma, California
Petaluma
$313 nightly
The price is $348
Nov 16 - Nov 17
Total with taxes and fees
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.

17. 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.
$727 nightly
The price is $822
Nov 24 - Nov 25
Total with taxes and fees
The Atlas Calistoga - Cottage #3
A wooden deck with outdoor seating and a covered area.

18. Spacious Beautiful Country Home on 8 Private Acres

Spacious Beautiful Country Home on 8 Private Acres
3.0 star property
Kelseyville
$603 nightly
The price is $672
Nov 15 - Nov 16
Total with taxes and fees
Spacious Beautiful Country Home on 8 Private Acres
A wooden pathway leading to a house with a view of a lake and mountains.

19. 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
Nov 22 - Nov 23
Total with taxes and fees
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

Learn more about Healdsburg

Stroll between tasting rooms in this charming wine country plaza where vintners pour small-batch Pinot Noir and Zinfandel. Bike through rolling vineyards in the morning, then spend afternoons browsing farm-to-table restaurants and artisan shops with locally-made olive oils.

See all hotels in Healdsburg
A vineyard sign with "Dry Creek Vineyard" written above a stone archway.

Top reviews in Healdsburg

A building with a tiled roof, arched windows, and a balcony with a railing.
Rancho Caymus Inn

Rancho Caymus Inn

Rancho Caymus Inn
St. Helena

10/10 Excellent

We absolutely loved the inn. The breakfast was wonderful and the staff was great and incredibly helpful. The facilities were clean and comfortable and extremely well-managed. Our needs were attended whenever we needed something or advice on where to go. The burritos across the street were also AMAZING! Can’t wait to stay here again on our next trip to the area.
United States
Christine
Reviewed August 4, 2025
Rancho Caymus Inn

Frequently Asked Questions

How much do cottages in Healdsburg cost?

Prepare to pay between $192 and $966 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 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