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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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Healdsburg holiday 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, (131 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
The price is AU$167
includes taxes & fees
14 Sept - 15 Sept
Wildhaven Sonoma Glamping
A hot tub on a wooden deck with a view of a forested area.

2. Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Guerneville
9.0 out of 10, Wonderful, (6 reviews)
"Our stay was fantastic! The cabin was everything we needed for a few days; cozy, and quiet. The outdoor spaces were great and the hot tub was perfect at the end of the day. The host was super helpful and responded to my questions almost immediately. "
United States
Rosa N.
The price is AU$598
includes taxes & fees
13 Sept - 14 Sept
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
A wooden sauna structure with a bench inside, a small pool, and a potted plant outside.

3. Wildflower

Wildflower
Windsor
10.0 out of 10, Exceptional, (1 review)
"Very accommodating home with all the essentials. Awesome backyard for the dogs, great location and communication. "
United States
Keri S.
The price is AU$1,281
includes taxes & fees
16 Sept - 17 Sept
Wildflower
A spacious living room with a wooden ceiling, large windows, and a sectional sofa.

4. Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C

Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
Forestville
10.0 out of 10, Exceptional, (4 reviews)
"Loved our stay. Well stocked kitchen and close to some great little wineries."
United States
Ellen B.
The price is AU$758
includes taxes & fees
13 Sept - 14 Sept
Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
A wooden interior with a dining area, a bench, and a mirror on the wall.

5. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (23 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is AU$771
includes taxes & fees
13 Sept - 14 Sept
Cozy Riverfront Cabin - Beach Access & Wood Stove
A kitchen with white cabinets, a wooden table, and a bar stool. There is a window with a view of the outside.

6. Tranquil Redwood Retreat

Tranquil Redwood Retreat
Guerneville
8.8 out of 10, Excellent, (13 reviews)
"Perfect hun for enjoying downtown guernville "
United States
Alex A.
The price is AU$480
includes taxes & fees
14 Sept - 15 Sept
Tranquil Redwood Retreat
A room with a white sofa, a black leather chair, a cowhide rug, and a white chair.

7. Creekside Under the Redwoods

Creekside Under the Redwoods
Guerneville
9.8 out of 10, Exceptional, (21 reviews)
"Very cute and comfortable place! We enjoyed our stay!"
United States
Kathy M.
The price is AU$480
includes taxes & fees
14 Sept - 15 Sept
Creekside Under the Redwoods
A wooden deck with two Adirondack chairs, a small table, and a sign indicating 'SANTA CLARA.'

8. Russian River Retreat: Private Beach & DogFriendly

Russian River Retreat: Private Beach & DogFriendly
Forestville
10.0 out of 10, Exceptional, (1 review)
"Love this place so much! Will rent it every year for my birthday if they’ll let me!"
United States
Anna K.
The price is AU$967
includes taxes & fees
20 Sept - 21 Sept
Russian River Retreat: Private Beach & DogFriendly
A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

9. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Healdsburg
9.8 out of 10, Exceptional, (17 reviews)
"The house was just like advertised. Great location to visit the surrounding area."
United States
David S.
The price is AU$539
includes taxes & fees
21 Sept - 22 Sept
Vineyard View Retreat • Fire Pit • Wine Tasting Perks

10. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Northwest Santa Rosa
9.4 out of 10, Exceptional, (23 reviews)
"very nice space "
United States
kevin c.
The price is AU$535
includes taxes & fees
14 Sept - 15 Sept
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

11. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is AU$511
includes taxes & fees
14 Sept - 15 Sept
Wine Country Cottage Escape
A patio with outdoor seating, a hot tub, and string lights.

12. Healdsburg Plaza Gem-Hot Tub and Tastings Included

Healdsburg Plaza Gem-Hot Tub and Tastings Included
Healdsburg
9.8 out of 10, Exceptional, (48 reviews)
"Great location and charming cottage. "
United States
Christopher T.
The price is AU$2,156
includes taxes & fees
28 Sept - 29 Sept
Healdsburg Plaza Gem-Hot Tub and Tastings Included
An outdoor patio with a pergola labeled 'Brewing Station,' surrounded by chairs and a table, with string lights overhead.

13. Russian River Brew-cation Home

Russian River Brew-cation Home
Northwest Santa Rosa
10.0 out of 10, Exceptional, (56 reviews)
"What a perfect place to stay for a wine country weekend! We’ll definitely be back!"
United States
Gina N.
Russian River Brew-cation Home
A deck with outdoor seating, hot tubs, and a glass door leading to a forested area.

14. River View Lodge - Hot Tub and Tastings Included

River View Lodge - Hot Tub and Tastings Included
Healdsburg
9.6 out of 10, Exceptional, (75 reviews)
"View was lovely. The Hot tub was great. Beds were very comfy!"
United States
Julie B.
The price is AU$1,581
includes taxes & fees
22 Sept - 23 Sept
River View Lodge - Hot Tub and Tastings Included
A living room with a fireplace, leather sofas, a glass coffee table, and a guitar.

15. Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries

Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Northwest Santa Rosa
9.8 out of 10, Exceptional, (75 reviews)
"Great place close to KJ and La Crema wineries!"
United States
Nancy P.
The price is AU$961
includes taxes & fees
13 Sept - 14 Sept
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
A modern kitchen with a central island, bar stools, a stainless steel refrigerator, and a backsplash with a geometric pattern.

16. Vineyard Vue - Wine Tastings Included

Vineyard Vue - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (39 reviews)
"Had a great time staying at Vineyard Vue"
United States
Grace N.
The price is AU$2,779
includes taxes & fees
30 Sept - 1 Oct
Vineyard Vue - Wine Tastings Included
A modern house with a deck, outdoor seating, and a large glass door leading to an interior space.

17. Private Vineyard Haven with Pool, Hot Tub and Tastings Included

Private Vineyard Haven with Pool, Hot Tub and Tastings Included
Healdsburg
9.8 out of 10, Exceptional, (68 reviews)
"Great location for touring wineries in the area. Very nice accommodations for 2 couples."
United States
Rock R.
Private Vineyard Haven with Pool, Hot Tub and Tastings Included
A wooden house with a stone staircase leading to a deck, surrounded by palm trees and a stone wall.

18. Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar

Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar
Geyserville
9.2 out of 10, Wonderful, (23 reviews)
"Fabulous property perfect for our needs. Family was able to stay together eat meals together in the big kitchen enjoy fantastic outdoor time together - really nice ambience and breathtaking views."
United States
Margo R.
The price is AU$1,732
includes taxes & fees
14 Sept - 15 Sept
Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar
A kitchen with a granite countertop, a fruit bowl, and a dining area with chairs and a table.

19. Elegant Vineyard Living at a Private Wine Country Estate

Elegant Vineyard Living at a Private Wine Country Estate
Windsor
8.4 out of 10, Very good, (6 reviews)
"What an amazing place! The hosts made it very easy to be prepared for our stay."
United States
Eric B.
The price is AU$1,482
includes taxes & fees
14 Sept - 15 Sept
Elegant Vineyard Living at a Private Wine Country Estate
A modern building entrance with a stone facade, a wooden pergola, and two wall-mounted lights.

20. Luxury Private Estate at Zoella Vineyards in the heart of Wine Country

Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
Healdsburg
9.6 out of 10, Exceptional, (67 reviews)
"Unbelievable property – we will absolutely stay here again –Just fabulous!"
United States
Jeffrey S.
The price is AU$3,072
includes taxes & fees
14 Sept - 15 Sept
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
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

The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton

10/10 Excellent
"This is the second time I’ve stayed here and I will definitely stay again the next time I’m back in Healdsburg. The location is really good it’s a lovely small walk on a path to downtown. It’s super clean and the beds are very comfortable. The rooms have cute little patios too! And it’s a dog friendly place. Highly recommend!"
Rebecca 1-night trip
Posted 5 hours ago
The Lodge at Healdsburg, Tapestry Collection by Hilton

Find out more about Healdsburg

Everything you need to know about Healdsburg holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Healdsburg holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Healdsburg holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Healdsburg holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Healdsburg holiday rentals we have selected for you start as low as AU$125 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Healdsburg rentals

At Expedia, we put the best Healdsburg holiday 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 holiday.

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 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?

Bodega Bay - Sonoma Coastline: This holiday home rental outside of Healdsburg is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a garden and a selection of books.

How many holiday rentals are there in Healdsburg?

Expedia has 137 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.