Healdsburg Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Healdsburg vacation rentals

A cozy cabin with a loft bedroom, wooden exterior, and a small balcony.

1. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (140 reviews)
"Awesome place to stay . So fun"
United States
Amy
The price is CA $140
CA $159 total
includes taxes & fees
Dec 14 - Dec 15
Wildhaven Sonoma Glamping
A room with a brown sofa, two wicker chairs, a small table, and a lamp.

2. Hideaway Cottages

Hideaway Cottages
2.0 star property
Calistoga
8.0 out of 10, Very good, (3 reviews)
"Old but quaint. No amenities, no updates. Coffee cups looked like thrift shop purchases. Bed was comfortable. Bath shower drained poorly. Too expensive for a 2 star property."
United States
Chris
The price is CA $310
CA $357 total
includes taxes & fees
Dec 14 - Dec 15
Hideaway Cottages
A single-story cabin with a small porch, situated on a hillside overlooking a body of water and mountains.

3. The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.0 out of 10, Wonderful, (10 reviews)
"Enjoyed my stay"
United States
Epeli
The price is CA $113
CA $129 total
includes taxes & fees
Nov 17 - Nov 18
The Ranch at Lake Sonoma
A view from a window overlooking a lake with a dock and greenery.

4. Clear Lake Cottages & Marina

Clear Lake Cottages & Marina
2.5 star property
Clearlake
9.2 out of 10, Wonderful, (396 reviews)
"All of positive things such as a lake view, clean room, and nice staff made a good memory for my family"
United States
leila karbalaei
The price is CA $204
CA $227 total
includes taxes & fees
Nov 15 - Nov 16
Clear Lake Cottages & Marina
A bedroom with a bed, a small table, and a chair, a bathroom with a sink and a mirror, and a sliding glass door leading to an outdoor area.

5. Mandala Springs Wellness Retreat Center

Mandala Springs Wellness Retreat Center
3.5 star property
Cobb
8.8 out of 10, Excellent, (39 reviews)
"Waterfront cabins were amazing. The location and wildlife were serene, fantastic place to stay."
United States
Carmino
The price is CA $191
CA $213 total
includes taxes & fees
Nov 17 - Nov 18
Mandala Springs Wellness Retreat Center
A kitchen with a stainless steel faucet, a microwave, and an oven.

6. Suites On Main

Suites On Main
2.0 star property
Kelseyville
9.0 out of 10, Wonderful, (4 reviews)
"Staff is great! They were right there to answer any questions or to assist with our needs. Our suite was very spacious, clean and great ambiance. Great restaurant the Saw Shop a block away and coffee & pastries across the street. We very much enjoyed our stay and will stay again."
United States
Margaret
The price is CA $278
CA $410 total
includes taxes & fees
Nov 15 - Nov 16
Suites On Main
A spacious living area with a sectional sofa, a blue armchair, and a dining table.

7. 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 CA $599
CA $1,379 total
includes taxes & fees
Nov 18 - Nov 19
Dog-friendly Haven w/ Stunning Views in Bodega Bay
A kitchen with a central island, wooden cabinets, and a large window overlooking a deck.

8. Spacious Beautiful Country Home on 8 Private Acres

Spacious Beautiful Country Home on 8 Private Acres
3.0 star property
Kelseyville
The price is CA $476
CA $958 total
includes taxes & fees
Nov 16 - Nov 17
Spacious Beautiful Country Home on 8 Private Acres
A modern kitchen with wooden cabinets, stainless steel appliances, and a glass door refrigerator.

9. Private Pool & Large Deck: Modern Cotati Villa!

Private Pool & Large Deck: Modern Cotati Villa!
4.0 star property
Cotati
The price is CA $599
CA $1,578 total
includes taxes & fees
Nov 15 - Nov 16
Private Pool & Large Deck: Modern Cotati Villa!
A wooden pathway leading to a house with a view of a lake and mountains.

10. 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 CA $245
CA $390 total
includes taxes & fees
Nov 22 - Nov 23
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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Top Healdsburg Hotel Reviews

A stone fireplace with a fire, outdoor seating with chairs and a table, and a sign reading "Rancho Cayman Inn".
Rancho Caymus Inn

Rancho Caymus Inn

Rancho Caymus Inn
St. Helena

10/10 Excellent

Perfect little retreat.
Canada
Grant
Reviewed October 30, 2026
Rancho Caymus Inn

Find out more about Healdsburg

Everything you need to know about Healdsburg vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Healdsburg vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Healdsburg vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Healdsburg vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Healdsburg. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Healdsburg vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Healdsburg vacation rentals we have selected for you start as low as CA $139 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Healdsburg rentals

At Expedia, we put the best Healdsburg vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Healdsburg rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Healdsburg vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Healdsburg. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there vacation rentals in Healdsburg?

Yes, there are vacation rentals in Healdsburg near Healdsburg Center for the Arts, or you can choose a secluded option if you want a relaxing stay. Visitors like the array of shops and scenic riverfront in Healdsburg. While you're here, grab a bite or have a drink at the wineries and top-notch restaurants.

What's the top vacation rental that Healdsburg has to offer?

DOG-FRIENDLY, COZY—PERFECT 4 COUPLES—Close to EVERYTHING. SPECIAL DISCOUNTS!: This vacation home rental outside of Healdsburg is located on the waterfront and has a balcony, a selection of books, and a Smart TV to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Healdsburg?

Expedia has 135 vacation rentals for your stay in Healdsburg.

What can I see and do in Healdsburg?

Russian River and Healdsburg Ridge Open Space Preserve are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include SingleThread Farm at Dry Creek. Healdsburg Plaza and Jordan Vineyard & Winery are other places to visit while you're in town.

What are vacation rentals like in Healdsburg?

Vacation rentals are privately owned properties you can book for several days or more in Healdsburg. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for small groups.