Healdsburg Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Healdsburg vacation rentals

Deluxe Cabin, 1 Queen Bed, Patio, Garden View | Laptop workspace, free WiFi, bed sheets

Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (112 reviews)
"Nice location to go and have a good time in the family "
United States
Ismelda Cortez
The price is ￥26,587
￥30,309 total
includes taxes & fees
Jul 7 - Jul 8
Wildhaven Sonoma Glamping
Terrace/patio

Private Vineyard Retreat • Wine Tasting Perks • Fire Pit

Private Vineyard Retreat • Wine Tasting Perks • Fire Pit
Healdsburg
10.0 out of 10, Exceptional, (14 reviews)
"This is a great property! Everything about it from the beginning to the end was amazing. Our two fur babies agree as well. Glenn is a great host, always available if needed. Definitely would stay again. "
United States
Audie P.
The price is ￥26,173
￥63,545 total
includes taxes & fees
Jun 30 - Jul 1
Private Vineyard Retreat • Wine Tasting Perks • Fire Pit
Fridge, microwave, oven, stovetop

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 ￥30,647
￥75,505 total
includes taxes & fees
Jun 24 - Jun 25
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Interior

Creekside Under the Redwoods

Creekside Under the Redwoods
Guerneville
9.8 out of 10, Exceptional, (20 reviews)
"Very cute and comfortable place! We enjoyed our stay!"
United States
Kathy M.
The price is ￥24,428
￥56,278 total
includes taxes & fees
Jun 24 - Jun 25
Creekside Under the Redwoods
TV, fireplace

Tranquil Redwood Retreat

Tranquil Redwood Retreat
Guerneville
8.8 out of 10, Excellent, (10 reviews)
"Perfect hun for enjoying downtown guernville "
United States
Alex A.
The price is ￥24,389
￥56,026 total
includes taxes & fees
Jul 21 - Jul 22
Tranquil Redwood Retreat
TV, fireplace, books, offices

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, (1 review)
"Loved our stay. Well stocked kitchen and close to some great little wineries."
United States
Ellen B.
The price is ￥46,799
￥106,075 total
includes taxes & fees
Jun 25 - Jun 26
Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
Dining

Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is ￥26,615
￥59,940 total
includes taxes & fees
Jun 25 - Jun 26
Wine Country Cottage Escape
Outdoor dining

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

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Guerneville
8.0 out of 10, Very Good, (2 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 ￥24,615
￥74,038 total
includes taxes & fees
Jun 24 - Jun 25
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Exterior detail

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

Farm Country Cottage in Downtown Geyserville, Vineyard Views + UNTI Wine
Geyserville
10.0 out of 10, Exceptional, (2 reviews)
"Cozy, rustic, and with all great amenities."
United States
Gina I.
The price is ￥32,260
￥61,133 total
includes taxes & fees
Jul 9 - Jul 10
Farm Country Cottage in Downtown Geyserville, Vineyard Views + UNTI Wine
Pool

Lodge Room for 2-3 people

Lodge Room for 2-3 people
Geyserville
The price is ￥19,164
￥24,690 total
includes taxes & fees
Jun 24 - Jun 25
Lodge Room for 2-3 people
TV, fireplace

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, (73 reviews)
"Great place close to KJ and La Crema wineries!"
United States
Nancy P.
The price is ￥37,422
￥87,277 total
includes taxes & fees
Jun 28 - Jun 29
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Outdoor pool, a heated pool

Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6

Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6
Windsor
10.0 out of 10, Exceptional, (1 review)
The price is ￥32,260
￥60,791 total
includes taxes & fees
Jul 5 - Jul 6
Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6
Dining

Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts

Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
Northwest Santa Rosa
10.0 out of 10, Exceptional, (82 reviews)
"We enjoyed our stay. We had a lovely girls weekend and had no issues. The owner was very responsive and helpful."
United States
Avani S.
The price is ￥45,883
￥99,369 total
includes taxes & fees
Jun 24 - Jun 25
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
Dining

Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.6 out of 10, Exceptional, (17 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is ￥60,104
￥128,405 total
includes taxes & fees
Jul 7 - Jul 8
Cozy Riverfront Cabin - Beach Access & Wood Stove
Outdoor dining

Healdsburg Charmer, Steps to Plaza + Hot Tub!

Healdsburg Charmer, Steps to Plaza + Hot Tub!
Healdsburg
10.0 out of 10, Exceptional, (18 reviews)
"Clementine Cottage is perfect for a trip to Healdsburg. The place is immaculate, the outdoor space is lovely and the proximity to restaurants and tasting rooms is perfect. The bed was very comfortable. I would definitely stay again."
United States
Gail B.
The price is ￥81,465
￥146,374 total
includes taxes & fees
Jul 13 - Jul 14
Healdsburg Charmer, Steps to Plaza + Hot Tub!
Terrace/patio

Russian River Retreat: Private Beach & DogFriendly

Russian River Retreat: Private Beach & DogFriendly
Forestville
The price is ￥41,364
￥115,136 total
includes taxes & fees
Jun 24 - Jun 25
Russian River Retreat: Private Beach & DogFriendly
Terrace/patio

Vista Retreat-Hot Tub and Wine Tastings Included

Vista Retreat-Hot Tub and Wine Tastings Included
Guerneville
10.0 out of 10, Exceptional, (89 reviews)
"We enjoyed our time at this property. Ot was very clean and well stocked. Check in was easy and there was plenty of space to relax. The outdoor space was excellent although you are not as secluded as it seems in the pictures. "
United States
Vickie M.
The price is ￥56,061
￥153,252 total
includes taxes & fees
Jun 25 - Jun 26
Vista Retreat-Hot Tub and Wine Tastings Included
A heated pool

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Windsor
9.2 out of 10, Wonderful, (46 reviews)
"Check-in was a little difficult, but the condo itself was convenient and a great stay."
United States
SB L.
The price is ￥32,260
￥60,791 total
includes taxes & fees
Jul 5 - Jul 6
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
A heated pool

Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views
Santa Rosa
10.0 out of 10, Exceptional, (18 reviews)
"We had excellent communication and customer service from our host. The property had amazing views and a nice home comfortable feel."
United States
Padrick G.
The price is ￥101,450
￥182,660 total
includes taxes & fees
Jun 24 - Jun 25
Farpoint: Heated Infinity Pool, Mountain Views
Property grounds

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, (17 reviews)
"We were having a girlfriend’s birthday getaway and this place was just perfect. Comfortable, lots of room, well equipped, & beautiful views. Would definitely return! Host was really great too!"
United States
Sherry W.
The price is ￥114,684
￥204,806 total
includes taxes & fees
Jun 29 - Jun 30
Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar
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 Madrona

The Madrona

10/10 Excellent
"I cannot wait to return to this hotel. The breakfast, the lunch, the dinner were fantastic. The grounds were beautiful. Staff friendly."
Mabrie 2-night trip
Posted 7 hours ago
The Madrona

Find out more about Healdsburg

Search for holiday rentals in Healdsburg on Expedia! You can easily find your home rentals, villas, holiday apartments in Healdsburg using one of the methods below:

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Frequently asked questions

Are there vacation rentals in Healdsburg?

Yes, there are vacation rentals in Healdsburg near SingleThread Farm at Dry Creek, 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 top-notch restaurants and wineries.

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

Bird Watcher Paradise 2 Bedroom 2 Bath with Beautiful View: This vacation home rental outside of Healdsburg is located on the waterfront and has a fireplace, a balcony, and a barbecue grill 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 145 vacation rentals for your stay in Healdsburg.

What can I see and do in Healdsburg?

Healdsburg Ridge Open Space Preserve and Russian River 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.