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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 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$681
includes taxes & fees
3 Dec - 4 Dec
Country Carriage House in Downtown Geyserville, Vineyard Views
yard view of old growth stump, stairs to front door, gate from off-parking

2. 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.
The price is NZ$655
includes taxes & fees
9 Nov - 10 Nov
Pumpkin House Summary
A small, single-story house with a front porch, a chimney, and a door with a window above it.

3. 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
The price is NZ$796
includes taxes & fees
11 Nov - 12 Nov
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
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$343
includes taxes & fees
9 Nov - 10 Nov
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.
The price is NZ$815
includes taxes & fees
9 Nov - 10 Nov
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.
The price is NZ$758
includes taxes & fees
9 Nov - 10 Nov
Wine Country Cottage in downtown Santa Rosa, CA
A wooden deck with a red umbrella, a wooden chair, and a table.

7. Relaxing Beekeeper's Cottage with hot tub

Relaxing Beekeeper's Cottage with hot tub
Bodega Bay
10.0 out of 10, Exceptional, (22 reviews)
"The cottage was charming, clean and well appointed. "
United States
Edie H.
The price is NZ$1,109
includes taxes & fees
9 Nov - 10 Nov
Relaxing Beekeeper's Cottage with hot tub
A wooden pathway leading to a treehouse with a wooden deck and a staircase.

8. 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.
The price is NZ$1,027
includes taxes & fees
19 Nov - 20 Nov
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.

9. 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)
"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$815
includes taxes & fees
9 Nov - 10 Nov
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.

10. 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.
The price is NZ$480
includes taxes & fees
10 Nov - 11 Nov
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.

11. 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$1,744
includes taxes & fees
18 Nov - 19 Nov
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.

12. 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.
Ocean view, Huge backyard, 5 minutes walk to the beach
A wooden deck with a stone pathway leading to a hammock.

13. 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 NZ$866
includes taxes & fees
15 Nov - 16 Nov
Stunning Sauna Cottage Retreat on Private Vineyard
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, (85 reviews)
"Lovely spot for a getaway!"
United States
Lisa M.
The price is NZ$1,124
includes taxes & fees
16 Nov - 17 Nov
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
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
The price is NZ$607
includes taxes & fees
9 Nov - 10 Nov
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.
The Atlas Calistoga - Cottage #3
A wooden pathway leading to a house with a view of a lake and mountains.

18. 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$494
includes taxes & fees
22 Nov - 23 Nov
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.
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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

An outdoor dining area with tables and chairs under trees, string lights, and a view of the landscape.
Montage Healdsburg

Montage Healdsburg

Montage Healdsburg
Healdsburg

10/10 Excellent

Great service
Australia
Rhiana
Reviewed April 14, 2024
Montage Healdsburg

Frequently Asked Questions

How much do cottages in Healdsburg cost?

Prepare to pay between NZ$342 and NZ$1,744 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 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.