Healdsburg, CA Cottage Rentals from $192

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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

Geyserville

Gina I.

$340 nightly

Dec 3 - Dec 4

Total with taxes and fees

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

Calistoga

"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...

William

$292 nightly

Nov 19 - Nov 20

Total with taxes and fees

3. Pumpkin House Summary

Guerneville

Nathan B.

$335 nightly

Nov 15 - Nov 16

Total with taxes and fees

A wooden deck with wicker furniture and a metal table, overlooking a vineyard and hills.

4. Garden house with gas fireplace

Middletown

Amy

$192 nightly

Nov 15 - Nov 16

Total with taxes and fees

5. Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

Calistoga

Paul L.

$292 nightly

Nov 16 - Nov 17

Total with taxes and fees

A two-story house with a front porch, a mailbox, and a number 839 on the front wall.

6. Wine Country Cottage in downtown Santa Rosa, CA

Santa Rosa

joanne h.

$389 nightly

Nov 15 - Nov 16

Total with taxes and fees

A wooden pathway leading to a treehouse with a wooden deck and a staircase.

7. Hillside Retreat in the Redwoods | Hot Tub

Guerneville

John B.

$539 nightly

Nov 19 - Nov 20

Total with taxes and fees

A pathway flanked by neatly trimmed hedges and a large tree, leading to a white building with a porch.

8. Escape to wine country in your independent cottage in downtown Calistoga

Calistoga

Douglas F.

$292 nightly

Nov 19 - Nov 20

Total with taxes and fees

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

Kelseyville

Janneth M.

$239 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

Bodega Bay

$848 nightly

Nov 18 - Nov 19

Total with taxes and fees

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

Bodega Bay

Amber B.

$492 nightly

Nov 15 - Nov 16

Total with taxes and fees

A wooden cabin with a stone pathway leading to a porch.

12. Stunning Sauna Cottage Retreat on Private Vineyard

Sebastopol

Cesar R.

$415 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

Dillon Beach

Katie M.

$495 nightly

Nov 16 - Nov 17

Total with taxes and fees

A wooden pathway leading to a house with a green door and windows, surrounded by greenery and a tree.

14. Relaxing Beekeeper's Cottage with hot tub

Bodega Bay

Edie H.

$532 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

Sonoma

David B.

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

Petaluma

$313 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

Calistoga

Joel S.

$727 nightly

Nov 24 - Nov 25

Total with taxes and fees

A wooden deck with outdoor furniture, a covered area, and a view of trees and mountains.

18. Spacious Beautiful Country Home on 8 Private Acres

Kelseyville

$603 nightly

Nov 15 - Nov 16

Total with taxes and fees

A wooden pathway leading to a house with a view of a lake and mountains.

19. Watefront Getaway w/ Mtn Views & Dock in Clearlake

Clearlake

"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...

Jennifer

$245 nightly

Nov 22 - Nov 23

Total with taxes and fees

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

St. Helena

10/10 Excellent

Christine

A cabin with a wooden deck and a porch, surrounded by dense forest.

Highlands Resort - Adults Only

Guerneville

10/10 Excellent

Diane

A building with large windows and a tree in front.

Wydown Hotel

Downtown St. Helena

10/10 Excellent

Diane

A modern house with a well-lit entrance, a covered patio, and a landscaped garden.

Olea Hotel

Glen Ellen

10/10 Excellent

Anonymous traveler

A two-story building with a central entrance, large windows, and a balcony.

Liora Estate

Healdsburg

10/10 Excellent

This hotel is truly 5 stars. The staff was very accommodating upon arrival. The room was eloquent and inspiring with classical music already playing when we entered. After a long day of tastings, we were not in the mood to attend our dinner reservations, so thankfully the staff allowed us to order from the restaurant, Chalkboard, although it was a bit after the restaurant was technically 'closed'. The food was wonderful and kudos to the Chef! The bed was extremely comfortable. So much so that...

David

A row of cabins with outdoor seating areas, surrounded by a well-maintained garden and a forested backdrop.

Cottages on River Road

Guerneville

10/10 Excellent

Julie

A modern outdoor deck with a stone fireplace, overlooking a mountainous landscape.

Montage Healdsburg

Healdsburg

10/10 Excellent

Peter

A two-story house with a porch, a wooden fence, and a small garden area.

The Inn on Pine

Calistoga

10/10 Excellent

Dana

A two-story building with a covered outdoor seating area, a fire pit, and a sign indicating a no-entry zone.

Golden Haven Hot Springs

Calistoga

10/10 Excellent

Jessalyne

A modern hotel entrance with a stone facade, a curved overhang, and a sign welcoming guests to Rahrner Park.

Fairfield Inn & Suites by Marriott Santa Rosa Rohnert Park

Rohnert Park

10/10 Excellent

Rachel

A row of wooden cabins with red umbrellas, surrounded by lush greenery and a winding path.

Aurora Park Cottages

Calistoga

10/10 Excellent

Quetia

A large, stucco building with a central entrance, surrounded by lush greenery and potted plants.

Kenwood Inn and Spa

Kenwood

10/10 Excellent

Nestled amongst dozens of nearby vineyards, this picturesque inn provided all the comforts of an intimate b&b with the high end care of a boutique property. The grounds were serene and well kept with winding pathways covered by fragrant flowering trellises and sounds of bubbling fountains throughout. The amenities were well-catered. Cool waters upon check in and check out. Turndown service including chocolates, lit fireplace and a custom playlist on surround sound. The brunch included with the...

Anonymous traveler

A lodge with a stone facade, a porch, and a well-maintained garden.

Harvest Inn

Thoman

10/10 Excellent

My wife and I checked in here on our Honeymoon and we’re immediately greeted by some of the nicest people we’ve met so far. Extremely helpful and nice and they also upgraded us on our Honeymoon to a wonderful room looking out at the Vineyard. The room was incredible, large and very scenic. We even had our own in room fireplace. The staff is absolutely amazing, and that extends to the Harvest Kitchen which is located near check in. The food service was wonderful, including their pre fix menus....

Michael

A row of traditional European-style buildings with balconies and hanging plants, a clear sky, and a gravel path.

Southbridge Napa Valley

Downtown St. Helena

10/10 Excellent

Hoilun

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

Healdsburg Vacation Rentals
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Search Healdsburg Cottages

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Healdsburg cottages

1. Country Carriage House in Downtown Geyserville, Vineyard Views

2. Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown

3. Pumpkin House Summary

4. Garden house with gas fireplace

5. Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

6. Wine Country Cottage in downtown Santa Rosa, CA

7. Hillside Retreat in the Redwoods | Hot Tub

8. Escape to wine country in your independent cottage in downtown Calistoga

9. Hot tub lake wine Cottage State Park 4 mins away

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

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

12. Stunning Sauna Cottage Retreat on Private Vineyard

13. Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog

14. Relaxing Beekeeper's Cottage with hot tub

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

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

17. The Atlas Calistoga - Cottage #3

18. Spacious Beautiful Country Home on 8 Private Acres

19. Watefront Getaway w/ Mtn Views & Dock in Clearlake

Learn more about Healdsburg

Top reviews in Healdsburg

Rancho Caymus Inn

10/10 Excellent

Frequently Asked Questions

How much do cottages in Healdsburg cost?

How many cottages are there in Healdsburg?

Are there any family-friendly cottages in Healdsburg?

Why book your cottage in Healdsburg with Expedia?

How can I find cheap cottages in Healdsburg?

What is there to do in Healdsburg near my cottage?

Explore a world of travel with Expedia