Healdsburg Holiday Rentals

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Healdsburg holiday rentals

Terrace/patio

Peaceful Healdsburg Wine Country Retreat with Vineyard Views

Peaceful Healdsburg Wine Country Retreat with Vineyard Views
Healdsburg
10.0 out of 10, Exceptional, (10 reviews)
"Kitchen was great, easy area for our dog.."
United States
Brad G.
The price is HK$1,481
HK$3,207 total
includes taxes & fees
19 Apr - 20 Apr
Peaceful Healdsburg Wine Country Retreat with Vineyard Views
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)
"Loved our stay!!"
United States
kristen s.
The price is HK$1,669
HK$4,053 total
includes taxes & fees
20 Apr - 21 Apr
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Dining

Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.6 out of 10, Exceptional, (15 reviews)
"Great location on the river. Can't wait to come back in the summer."
United States
Gregg B.
The price is HK$1,054
HK$3,809 total
includes taxes & fees
19 Apr - 20 Apr
Cozy Riverfront Cabin - Beach Access & Wood Stove
Interior

Creekside Under the Redwoods

Creekside Under the Redwoods
Guerneville
9.8 out of 10, Exceptional, (18 reviews)
"Very cute and comfortable place! We enjoyed our stay!"
United States
Kathy M.
The price is HK$1,184
HK$2,522 total
includes taxes & fees
20 Apr - 21 Apr
Creekside Under the Redwoods
Outdoor dining

Heron House - Hot Tub and Wine Tastings Included

Heron House - Hot Tub and Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (27 reviews)
"Wonderful stay at the Heron house very comfortable and accommodating very peaceful which is what we always look for everything you need is here enjoyed our once of year trip to Healdsburg"
United States
Dean M.
Heron House - Hot Tub and Wine Tastings Included
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 HK$1,184
HK$2,522 total
includes taxes & fees
20 Apr - 21 Apr
Tranquil Redwood Retreat
Dining

Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is HK$1,293
HK$2,895 total
includes taxes & fees
21 Apr - 22 Apr
Wine Country Cottage Escape
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
The price is HK$1,567
HK$2,960 total
includes taxes & fees
19 Apr - 20 Apr
Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6
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)
"enjoyed our stay, no surprises and a good value"
United States
Craig M.
The price is HK$877
HK$2,853 total
includes taxes & fees
17 May - 18 May
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Dining

Russian River Brew-cation Home

Russian River Brew-cation Home
Northwest Santa Rosa
10.0 out of 10, Exceptional, (56 reviews)
"The house was great! We enjoyed our stay"
United States
Warren M.
The price is HK$1,778
HK$4,244 total
includes taxes & fees
19 Apr - 20 Apr
Russian River Brew-cation Home
A heated pool

Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views
Santa Rosa
10.0 out of 10, Exceptional, (12 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 HK$3,618
HK$7,444 total
includes taxes & fees
19 Apr - 20 Apr
Farpoint: Heated Infinity Pool, Mountain Views
Terrace/patio

Peaceful Redwood Hideaway - Hot Tub, Hammock, Walk to Russian River and Downtown

Peaceful Redwood Hideaway - Hot Tub, Hammock, Walk to Russian River and Downtown
Guerneville
10.0 out of 10, Exceptional, (50 reviews)
"Great location, very clean, private hot tub, bed was comfortable. "
United States
Peter J.
The price is HK$1,872
HK$3,748 total
includes taxes & fees
20 Apr - 21 Apr
Peaceful Redwood Hideaway - Hot Tub, Hammock, Walk to Russian River and Downtown
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 HK$1,512
HK$2,821 total
includes taxes & fees
27 Apr - 28 Apr
Farm Country Cottage in Downtown Geyserville, Vineyard Views + UNTI Wine
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, (45 reviews)
"Check-in was a little difficult, but the condo itself was convenient and a great stay."
United States
SB L.
The price is HK$1,567
HK$2,827 total
includes taxes & fees
19 Apr - 20 Apr
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 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, (81 reviews)
"We completely enjoyed our stay. We will be back next time we are in the area."
United States
Robert M.
The price is HK$1,731
HK$4,185 total
includes taxes & fees
21 Apr - 22 Apr
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
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
The price is HK$1,613
HK$4,482 total
includes taxes & fees
12 May - 13 May
Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
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, (16 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 HK$5,405
HK$9,629 total
includes taxes & fees
12 May - 13 May
Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar
Exterior

Healdsburg Plaza Charmer w/ Hot Tub!

Healdsburg Plaza Charmer w/ Hot Tub!
Healdsburg
10.0 out of 10, Exceptional, (18 reviews)
"great location! the cottage was perfect for our trip with pets."
United States
Sue P.
The price is HK$2,495
HK$5,209 total
includes taxes & fees
22 Apr - 23 Apr
Healdsburg Plaza Charmer w/ Hot Tub!
Fridge, microwave, oven, stovetop

Vineyard Vue - Wine Tastings Included

Vineyard Vue - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (37 reviews)
"Had a great time staying at Vineyard Vue"
United States
Grace N.
The price is HK$3,447
HK$7,469 total
includes taxes & fees
22 Apr - 23 Apr
Vineyard Vue - Wine Tastings Included
Terrace/patio

Sonoma Wine Country Home: Pool, Hot Tub & Fun!

Sonoma Wine Country Home: Pool, Hot Tub & Fun!
Windsor
10.0 out of 10, Exceptional, (9 reviews)
"The backyard is as fantastic as the pictures promise, and the pool was at an excellent temperature. Would definitely stay here again."
United States
Joshua J.
The price is HK$2,969
HK$11,237 total
includes taxes & fees
12 May - 13 May
Sonoma Wine Country Home: Pool, Hot Tub & Fun!
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

H2Hotel

H2Hotel

10/10 Excellent
"Clean room great bed beautiful bathroom and very spacious shower"
Rosanna 2-night trip
Posted 7 hours ago
H2Hotel

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:

  • View our selection of featured holiday rentals in Healdsburg
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  • Enter your travel dates to view the best deals on holiday rentals in Healdsburg while they last

Look no further and take a look at our great range of rental properties in Healdsburg!

Frequently asked questions

Are there holiday rentals in Healdsburg?

Yes, there are holiday rentals in Healdsburg close to SingleThread Farm at Dry Creek, 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 top-notch restaurants and wineries.

What are some of the best holiday rentals that Healdsburg has to offer?

Bodega Bay - Pacific Ocean Edge: 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. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in Healdsburg?

Expedia has 143 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.