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

Healdsburg Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (133 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
The price is CA $150
CA $171 total
includes taxes & fees
Sep 28 - Sep 29
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
9.4 out of 10, Exceptional, (9 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 CA $194
CA $617 total
includes taxes & fees
Sep 28 - Sep 29
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

3. 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)
"Great location!"
United States
Riley F.
The price is CA $242
CA $572 total
includes taxes & fees
Sep 29 - Sep 30
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
A deck with red Adirondack chairs, a fire pit, and a wooden staircase leading to a house.

4. 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 CA $214
CA $490 total
includes taxes & fees
Sep 28 - Sep 29
Tranquil Redwood Retreat
A spacious living room with a wooden ceiling, large windows, and a sectional sofa.

5. 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, (6 reviews)
"Loved our stay. Well stocked kitchen and close to some great little wineries."
United States
Ellen B.
The price is CA $262
CA $766 total
includes taxes & fees
Sep 28 - Sep 29
Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C

6. 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 CA $165
CA $530 total
includes taxes & fees
Sep 29 - Sep 30
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A wooden interior with a dining area, a bench, and a mirror on the wall.

7. 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 CA $211
CA $717 total
includes taxes & fees
Oct 5 - Oct 6
Cozy Riverfront Cabin - Beach Access & Wood Stove
A modern building with a metal exterior, a wooden door, and a small window on the side.

8. Country Carriage House in Downtown Geyserville, Vineyard Views

Country Carriage House in Downtown Geyserville, Vineyard Views
Geyserville
10.0 out of 10, Exceptional, (5 reviews)
"Cozy, rustic, and with all great amenities."
United States
Gina I.
The price is CA $231
CA $554 total
includes taxes & fees
Oct 22 - Oct 23
Country Carriage House in Downtown Geyserville, Vineyard Views
A wooden deck with two Adirondack chairs, a small table, and a sign indicating 'SANTA CLARA.'

9. 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 CA $321
CA $945 total
includes taxes & fees
Sep 30 - Oct 1
Russian River Retreat: Private Beach & DogFriendly
A two-story house with a covered porch and a gravel driveway.

10. Enchanting Retreat in the heart of Redwoods

Enchanting Retreat in the heart of Redwoods
Guerneville
8.4 out of 10, Very good, (15 reviews)
"Great place to stay clean quiet peaceful loved it "
United States
Josie B.
The price is CA $199
CA $471 total
includes taxes & fees
Sep 28 - Sep 29
Enchanting Retreat in the heart of Redwoods
A patio with outdoor seating, a hot tub, and string lights.

11. 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 CA $916
CA $1,879 total
includes taxes & fees
Sep 28 - Sep 29
Healdsburg Plaza Gem-Hot Tub and Tastings Included
A deck with outdoor seating, hot tubs, and a glass door leading to a forested area.

12. 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 CA $676
CA $1,604 total
includes taxes & fees
Sep 28 - Sep 29
River View Lodge - Hot Tub and Tastings Included
A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

13. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is CA $233
CA $523 total
includes taxes & fees
Sep 28 - Sep 29
Wine Country Cottage Escape
A covered patio with a dining table, chairs, and a sofa.

14. Redwood Riverfront - Hot Tub and Tastings Included

Redwood Riverfront - Hot Tub and Tastings Included
Healdsburg
9.2 out of 10, Wonderful, (69 reviews)
"We had a decent stay at Riverfront. Having the house by the river was pleasant. We were a bit disappointed to find that the hot tub was below the deck and we couldnt use it at night since there seem to be no outdoor light. Overall it was nice secluded stay."
United States
Kenneth M.
The price is CA $740
CA $1,688 total
includes taxes & fees
Oct 6 - Oct 7
Redwood Riverfront - Hot Tub and Tastings Included
A swimming pool with lounge chairs and an umbrella, surrounded by a grassy area and trees.

15. Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg

Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg
Healdsburg
9.6 out of 10, Exceptional, (193 reviews)
"Great location and cozy home."
United States
Kelly B.
The price is CA $742
CA $1,385 total
includes taxes & fees
Sep 28 - Sep 29
Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg
An outdoor patio with a pergola labeled 'Brewing Station,' surrounded by chairs and a table, with string lights overhead.

16. 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.
The price is CA $286
CA $724 total
includes taxes & fees
Sep 28 - Sep 29
Russian River Brew-cation Home
A wooden sauna structure with a bench inside, a small pool, and a potted plant outside.

17. 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 CA $373
CA $1,447 total
includes taxes & fees
Oct 13 - Oct 14
Wildflower
A living room with a fireplace, leather sofas, a glass coffee table, and a guitar.

18. 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, (76 reviews)
"Our stay was very comfortable."
United States
Kim R.
The price is CA $488
CA $967 total
includes taxes & fees
Oct 5 - Oct 6
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
A modern house with a deck, outdoor seating, and a large glass door leading to an interior space.

19. 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, (69 reviews)
"Great location for touring wineries in the area. Very nice accommodations for 2 couples."
United States
Rock R.
The price is CA $1,262
CA $2,368 total
includes taxes & fees
Sep 29 - Sep 30
Private Vineyard Haven with Pool, Hot Tub and Tastings Included
A modern kitchen with a central island, bar stools, a stainless steel refrigerator, and a backsplash with a geometric pattern.

20. 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 CA $1,544
CA $2,739 total
includes taxes & fees
Sep 30 - Oct 1
Vineyard Vue - Wine Tastings Included
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

Hotel Trio Healdsburg

Hotel Trio Healdsburg

10/10 Excellent
"Clean room, comfortable beds, nice pool, no jacuzzi. Used the bicycles to ride to the plaza. Friendly staff"
Vince 3-night trip
Posted less than an hour ago
Hotel Trio Healdsburg

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 $128 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.