Healdsburg Holiday Rentals

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Healdsburg holiday rentals

Laptop workspace, free WiFi, bed sheets

Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.0 out of 10, Wonderful, (107 reviews)
"Nice location to go and have a good time in the family "
United States
Ismelda Cortez
The price is HK$884
HK$1,008 total
includes taxes & fees
3 Jun - 4 Jun
Wildhaven Sonoma Glamping
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$1,810
HK$4,216 total
includes taxes & fees
8 Jun - 9 Jun
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
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 completely enjoyed our stay. We will be back next time we are in the area."
United States
Robert M.
The price is HK$2,226
HK$4,749 total
includes taxes & fees
3 Jun - 4 Jun
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
Outdoor dining

Healdsburg Plaza Charmer with Hot Tub!

Healdsburg Plaza Charmer with 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$3,358
HK$6,462 total
includes taxes & fees
30 Jun - 1 Jul
Healdsburg Plaza Charmer with Hot Tub!
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 HK$2,292
HK$5,386 total
includes taxes & fees
7 Jun - 8 Jun
Cozy Riverfront Cabin - Beach Access & Wood Stove
Outdoor 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$1,803
HK$4,265 total
includes taxes & fees
3 Jun - 4 Jun
Russian River Brew-cation Home
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 HK$1,309
HK$3,400 total
includes taxes & fees
3 Jun - 4 Jun
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Outdoor pool, a heated pool

TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6

TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6
Windsor
The price is HK$1,567
HK$2,946 total
includes taxes & fees
3 Jun - 4 Jun
TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6
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 HK$1,076
HK$3,402 total
includes taxes & fees
3 Jun - 4 Jun
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Exterior detail

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, (66 reviews)
"Better than expected!! We loved this properly and would most definitely stay again!! It was perfect and magical in every way!!! "
United States
Elaine G.
The price is HK$6,270
HK$11,380 total
includes taxes & fees
3 Jun - 4 Jun
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
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 HK$1,185
HK$2,707 total
includes taxes & fees
3 Jun - 4 Jun
Creekside Under the Redwoods
A heated pool

Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views
Santa Rosa
10.0 out of 10, Exceptional, (16 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$4,929
HK$8,993 total
includes taxes & fees
4 Jun - 5 Jun
Farpoint: Heated Infinity Pool, Mountain Views
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 HK$1,452
HK$4,214 total
includes taxes & fees
3 Jun - 4 Jun
Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
Terrace/patio

Dry Creek Valley Home and Vineyard

Dry Creek Valley Home and Vineyard
Healdsburg
The price is HK$7,415
HK$11,999 total
includes taxes & fees
7 Jun - 8 Jun
Dry Creek Valley Home and Vineyard
Terrace/patio

Rustic cabin w/ decks & hot tub near river

Rustic cabin w/ decks & hot tub near river
Guerneville
9.4 out of 10, Exceptional, (3 reviews)
"It was a great place!"
United States
Lauren H.
The price is HK$1,234
HK$3,603 total
includes taxes & fees
8 Jun - 9 Jun
Rustic cabin w/ decks & hot tub near river
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
9.4 out of 10, Exceptional, (18 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$4,373
HK$8,334 total
includes taxes & fees
3 Jun - 4 Jun
Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar
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$2,946 total
includes taxes & fees
3 Jun - 4 Jun
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
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)
"Kitchen was great, easy area for our dog.."
United States
Brad G.
The price is HK$1,622
HK$3,485 total
includes taxes & fees
30 Jun - 1 Jul
Private Vineyard Retreat • Wine Tasting Perks • Fire Pit
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$1,567
HK$2,963 total
includes taxes & fees
17 Jun - 18 Jun
Farm Country Cottage in Downtown Geyserville, Vineyard Views + UNTI Wine
Interior

Lovely Tudor Home w/ Pool & Spa Near Russian River

Lovely Tudor Home w/ Pool & Spa Near Russian River
Guerneville
9.6 out of 10, Exceptional, (125 reviews)
"Everything you need was there. Stunning grounds, great communication, simply lovely."
United States
Sam F.
The price is HK$4,916
HK$10,311 total
includes taxes & fees
9 Jun - 10 Jun
Lovely Tudor Home w/ Pool & Spa Near Russian River
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
"Coffee shop and general store within walking distance and very good"
Joseph E 2-night trip
Posted 19 hours ago
The Lodge at Healdsburg, Tapestry Collection by Hilton

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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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 wineries and top-notch restaurants.

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

DOG-FRIENDLY, COZY—PERFECT 4 COUPLES—BOOK 3 NIGHTS—4th FREE! Close to EVERYTHING: 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 142 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.