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

Healdsburg Holiday Rentals

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Our top choices for Healdsburg holiday rentals

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 NZ$199
includes taxes & fees
13 Dec - 14 Dec
Wildhaven Sonoma Glamping

2. Hideaway Cottages

Hideaway Cottages
2.0 star property
Calistoga
4.0 out of 10, (1 review)
"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 NZ$431
includes taxes & fees
19 Nov - 20 Nov
Hideaway Cottages

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 NZ$161
includes taxes & fees
13 Nov - 14 Nov
The Ranch at Lake Sonoma

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 NZ$279
includes taxes & fees
13 Dec - 14 Dec
Clear Lake Cottages & Marina

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 NZ$279
includes taxes & fees
16 Nov - 17 Nov
Mandala Springs Wellness Retreat Center

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 NZ$513
includes taxes & fees
15 Nov - 16 Nov
Suites On Main

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 NZ$1,725
includes taxes & fees
18 Nov - 19 Nov
Dog-friendly Haven w/ Stunning Views in Bodega Bay

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 NZ$1,200
includes taxes & fees
15 Nov - 16 Nov
Spacious Beautiful Country Home on 8 Private Acres

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

Private Pool & Large Deck: Modern Cotati Villa!
4.0 star property
Cotati
The price is NZ$1,974
includes taxes & fees
15 Nov - 16 Nov
Private Pool & Large Deck: Modern Cotati Villa!

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 NZ$488
includes taxes & fees
23 Nov - 24 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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Top Healdsburg Hotel Reviews

Find out more about Healdsburg

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Healdsburg holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Healdsburg. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Healdsburg. Seeing all the best attractions is bound to make you fall in love with Healdsburg. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Healdsburg short-term rentals, that won’t be hard to do.

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Frequently asked questions

Are there holiday rentals in Healdsburg?

Yes, there are holiday rentals in Healdsburg close to Healdsburg Center for the Arts, or you can select a more secluded option if you're looking for 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 are some of the best holiday rentals that Healdsburg has to offer?

DOG-FRIENDLY, COZY—PERFECT 4 COUPLES—Close to EVERYTHING. SPECIAL DISCOUNTS!: This holiday 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 holiday rentals are there in Healdsburg?

Expedia has 135 holiday 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 holiday rentals like in Healdsburg?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Healdsburg. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family trip or a small group gathering.