A garden pathway lined with white roses leading to a building with a stone facade and a window.

Book a Healdsburg Cottage

  • 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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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 NZ$677
includes taxes & fees
22 Oct - 23 Oct
Country Carriage House in Downtown Geyserville, Vineyard Views

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 NZ$648
includes taxes & fees
27 Sept - 28 Sept
Pumpkin House Summary
A building with a sign that reads "Russian River Brewing Company."

3. 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.
The price is NZ$738
includes taxes & fees
1 Oct - 2 Oct
Wine Country Cottage in downtown Santa Rosa, CA
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
The price is NZ$347
includes taxes & fees
1 Oct - 2 Oct
Garden house with gas fireplace
A wooden deck with a round table and two chairs, surrounded by a white railing.

5. Comfort and Style in Our Queen Cottage

Comfort and Style in Our Queen Cottage
Calistoga
9.8 out of 10, Exceptional, (49 reviews)
The price is NZ$489
includes taxes & fees
25 Oct - 26 Oct
Comfort and Style in Our Queen Cottage
A wooden deck with a stone pathway leading to a hammock.

6. 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.
Stunning Sauna Cottage Retreat on Private Vineyard
A hot tub with a blue light, surrounded by a wooden fence and string lights.

7. 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.
The price is NZ$382
includes taxes & fees
27 Sept - 28 Sept
Hot tub lake wine Cottage State Park 4 mins away
A small, single-story house with a front porch, a chimney, and a door with a window above it.

8. 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, (45 reviews)
"Host, amenities, location….all excellent. "
United States
Amy B.
The price is NZ$811
includes taxes & fees
29 Sept - 30 Sept
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.

9. 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 NZ$746
includes taxes & fees
5 Oct - 6 Oct
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
A house with a porch, a wooden door, and two rocking chairs. There are two suitcases and a table with bottles on the porch.

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 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 NZ$746
includes taxes & fees
5 Oct - 6 Oct
Escape to wine country in your independent cottage in downtown Calistoga
A small, single-story house with a porch, a red door, and two bicycles parked outside.

11. 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 NZ$562
includes taxes & fees
27 Sept - 28 Sept
Charming King Cottage
A wooden pathway leading to a house with a view of a lake and mountains.

12. 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 NZ$478
includes taxes & fees
4 Oct - 5 Oct
Watefront Getaway w/ Mtn Views & Dock in Clearlake
A wooden deck with a view of a large tree, a fenced yard, and a distant body of water.

13. 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.
The price is NZ$950
includes taxes & fees
27 Sept - 28 Sept
Ocean view, Huge backyard, 5 minutes walk to the beach
A two-story house with a wooden deck and a covered front porch.

14. 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.
The price is NZ$992
includes taxes & fees
30 Sept - 1 Oct
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog

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 NZ$524
includes taxes & fees
28 Sept - 29 Sept
Antique Indonesian Teakwood Cottage for a Romantic Getaway in Petaluma, California
A deck with a sofa, a glass-top coffee table, and a view of a hilly landscape.

16. Dog-friendly Haven w/ Stunning Views in Bodega Bay

Dog-friendly Haven w/ Stunning Views in Bodega Bay
3.0 star property
Bodega Bay
The price is NZ$1,881
includes taxes & fees
2 Oct - 3 Oct
Dog-friendly Haven w/ Stunning Views in Bodega Bay
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

Hotel Trio Healdsburg

Hotel Trio Healdsburg

8/10 Good
"This hotel met my expectations which made my stay very pleasant and the staff was very attentive. A particular great amenity was the shuttle service to the downtown area."
David 1-night trip
Posted less than an hour ago
Hotel Trio Healdsburg

Find out more about Healdsburg

Healdsburg Cottages information

Number of reviews
294
Accommodation
16 Cottages
Lowest Price
NZ$347
Highest Price
NZ$1,881

Frequently asked questions

How much do cottages in Healdsburg cost?
Prepare to pay between NZ$347 and NZ$1,881 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 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.
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.