Healdsburg, CA Cottage Rentals

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

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Our top choices for Healdsburg cottages

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

Geyserville

Gina I.

$341 nightly

Aug 17 - Aug 18

Total with taxes and fees

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

Calistoga

Paul L.

$348 nightly

Aug 4 - Aug 5

Total with taxes and fees

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

Calistoga

"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!"

Jennifer G.

$346 nightly

Aug 4 - Aug 5

Total with taxes and fees

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

Calistoga

Amy B.

$340 nightly

Aug 16 - Aug 17

Total with taxes and fees

5. Charming King Cottage

Calistoga

Michael E. S.

$220 nightly

Aug 4 - Aug 5

Total with taxes and fees

6. Wine Country Cottage in downtown Santa Rosa, CA

Santa Rosa

Stan R.

$398 nightly

Aug 10 - Aug 11

Total with taxes and fees

7. Comfort and Style in Our Queen Cottage

Calistoga

Robert

$199 nightly

Aug 4 - Aug 5

Total with taxes and fees

8. The Atlas Calistoga - Cottage #1

Calistoga

Kris R.

$590 nightly

Aug 31 - Sep 1

Total with taxes and fees

9. Stunning Sauna Cottage Retreat on Private Vineyard

Sebastopol

Cesar R.

$474 nightly

Aug 12 - Aug 13

Total with taxes and fees

10. Garden house with gas fireplace

Middletown

"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...

kelsie i.

$234 nightly

Aug 16 - Aug 17

Total with taxes and fees

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

Dillon Beach

Lisa M.

$691 nightly

Aug 27 - Aug 28

Total with taxes and fees

12. 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

Aug 9 - Aug 10

Total with taxes and fees

13. Relaxing Beekeeper's Cottage with hot tub

Bodega Bay

Edie H.

$502 nightly

Aug 26 - Aug 27

Total with taxes and fees

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

Kelseyville

Julio L.

$209 nightly

Aug 10 - Aug 11

Total with taxes and fees

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

Petaluma

$292 nightly

Aug 6 - Aug 7

Total with taxes and fees

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Top Healdsburg Hotel Reviews

The Lodge at Healdsburg, Tapestry Collection by Hilton

8/10 Good

"Our stay was comfortable and the staff was friendly. However, being "senior citizens" when I asked about a bell man for our bags, we had not assistance at all. In the end, we discovered several carts to make carrying our carts easier. They were pointed out to us and we had to discover them accidentally. Food service was not that impressive. Our room was clean and neat and comfortable, though."

Liora Estate

10/10 Excellent

"The Liora Estate Hotel is gorgeous. Our high end restaurant was just around the corner. The location is right in the middle of things. The valet parking is complimentary and a real convenience. My favorite amenity was the spectacular breakfast delivered to the room in a basket. Everything you need to start the day."

Wildhaven Sonoma Glamping

8/10 Good

"Swimming in the river was the best part of the trip. Bring your water shoes; there are rocks and I almost lost my sandals three times . Bring an extra fan for the tent. If you are in a tent; bring a portable umbrella for the outside. Our bench was not covered by the trees most of the day and the sun was strong. It is hot in the tent during the summer; that’s when you go swimming or hiking during the day. We recommend going to riverfront park trail; it’s an easy hike 20 mins drive from wildheaven. And it is beautiful there. Oh bring a hoodie for the night time; it gets cold at night. Hot days and cold nights in the summer."

Find out more about Healdsburg

Healdsburg Cottages information

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Frequently asked questions

How much do cottages in Healdsburg cost?

Prepare to pay between and 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.

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Healdsburg Vacation Rentals

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OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Healdsburg cottages

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

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

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