Book Holiday Homes in Healdsburg

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Healdsburg

Wooded Restful Retreat, with broad scenic views, outdoor dining

Wooded Restful Retreat, with broad scenic views, outdoor dining

Healdsburg CA
With a stay at this vacation home, you'll be centrally located in Healdsburg, within a 5-minute drive of Russian River and Badger Dog Park.
Opens in a new windowWooded Restful Retreat, with broad scenic views, outdoor dining
Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi

Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi

Healdsburg CA
With a stay at this vacation home in Healdsburg, you'll be within a 10-minute drive of Russian River and Pezzi King Winery.
Opens in a new windowHealdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi
Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove

Guerneville CA
The price is AU$707 per night from 18 May to 19 May
AU$707
18 May - 19 May
includes taxes & fees
With a stay at this vacation home in Guerneville, you'll be on the beach, within a 10-minute drive of Russian River and Pee Wee Golf and Arcade.
Opens in a new windowCozy Riverfront Cabin - Beach Access & Wood Stove
Save an average of 15% on thousands of hotels when you're signed in
Spacious house in marvelous Healdsburg close to town

Spacious house in marvelous Healdsburg close to town

Healdsburg CA
With a stay at this vacation home in Healdsburg, you'll be a 5-minute walk from Russian River and 14 minutes by foot from Pezzi King Winery.
Opens in a new windowSpacious house in marvelous Healdsburg close to town
Luxurious Large Home, Beautiful Pool, Extensive Gardens

Luxurious Large Home, Beautiful Pool, Extensive Gardens

Guerneville CA
With a stay at this vacation home in Guerneville, you'll be by the sea, within a 5-minute drive of Russian River and Armstrong Redwoods State Park.
Opens in a new windowLuxurious Large Home, Beautiful Pool, Extensive Gardens
Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views

Santa Rosa CA
The price is AU$1,351 per night from 20 May to 21 May
AU$1,351
20 May - 21 May
includes taxes & fees
Located in Santa Rosa, this vacation home is in the mountains, within a 10-minute drive of Kendall-Jackson Wine Estate and Gardens and Sutter Santa Rosa Regional ...
Opens in a new windowFarpoint: Heated Infinity Pool, Mountain Views
Paradise: Riverfront 3 Bed 2 Bath + Hot Tub, Dock & Boats. 3/4 mile to town

Paradise: Riverfront 3 Bed 2 Bath + Hot Tub, Dock & Boats. 3/4 mile to town

Guerneville CA
When you stay at this vacation home in Guerneville, you'll be on the waterfront, just steps from Russian River and a 2-minute drive from Pee Wee Golf and ...
Opens in a new windowParadise: Riverfront 3 Bed 2 Bath + Hot Tub, Dock & Boats. 3/4 mile to town
4 Couples or 2 Families, Private and Prime Location, Pool and Hot Tub

4 Couples or 2 Families, Private and Prime Location, Pool and Hot Tub

Forestville CA
With a stay at this vacation home in Forestville, you'll be in the mountains, within a 10-minute drive of Russian River and Korbel Winery.
Opens in a new window4 Couples or 2 Families, Private and Prime Location, Pool and Hot Tub
Heart of Wine Country, Cute Cottage w/Hot Tub

Heart of Wine Country, Cute Cottage w/Hot Tub

Windsor CA
Located in Windsor, this vacation home is a 2-minute drive from Powell's Sweet Shoppe - Windsor and 6 minutes from Windsor Golf Club.
Opens in a new windowHeart of Wine Country, Cute Cottage w/Hot Tub
Don't see what you're looking for?
See all available properties in Healdsburg
View all properties
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.

Healdsburg Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Healdsburg vacation homes are the perfect way for you to wing it.

Holiday houses in Healdsburg let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Healdsburg in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Healdsburg adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Healdsburg with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Healdsburg vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Healdsburg Holiday Homes essential information

Accommodation
230 Holiday Homes
Lowest Price
AU$210
Highest Price
AU$1,351
Popular accommodation
Wooded Restful Retreat, with broad scenic views, outdoor dining, Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi, Cozy Riverfront Cabin - Beach Access & Wood Stove, Spacious house in marvelous Healdsburg close to town, Luxurious Large Home, Beautiful Pool, Extensive Gardens, Farpoint: Heated Infinity Pool, Mountain Views, Paradise: Riverfront 3 Bed 2 Bath + Hot Tub, Dock & Boats. 3/4 mile to town, 4 Couples or 2 Families, Private and Prime Location, Pool and Hot Tub , Heart of Wine Country, Cute Cottage w/Hot Tub

Top trending hotels in Healdsburg

Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta

3 out of 5
198 Dry Creek Road Healdsburg CA
Fully refundableReserve now, pay when you stay
The price is AU$210 per night from 17 May to 18 May
AU$210
17 May - 18 May
includes taxes & fees
Located in Healdsburg, Dry Creek Inn MOD Collection by Sonesta is in the suburbs, within a 5-minute drive of Healdsburg Plaza and Trentadue Winery.
Opens in a new windowDry Creek Inn MOD Collection by Sonesta
The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton

3.5 out of 5
1261 Grove St Healdsburg CA
Fully refundableReserve now, pay when you stay
The price is AU$247 per night from 25 May to 26 May
AU$247
25 May - 26 May
includes taxes & fees
With a stay at The Lodge at Healdsburg, Tapestry Collection by Hilton in Healdsburg, you'll be within a 10-minute drive of Russian River and Krug Event ...
Opens in a new windowThe Lodge at Healdsburg, Tapestry Collection by Hilton
Hotel Trio Healdsburg

Hotel Trio Healdsburg

3 out of 5
110 Dry Creek Rd Healdsburg CA
Fully refundableReserve now, pay when you stay
The price is AU$314 per night from 25 May to 26 May
AU$314
25 May - 26 May
includes taxes & fees
With a stay at Hotel Trio Healdsburg in Healdsburg, you'll be within a 10-minute drive of Russian River and Krug Event Center.
Opens in a new windowHotel Trio Healdsburg
Save an average of 15% on thousands of hotels when you're signed in
H2Hotel

H2Hotel

4 out of 5
219 Healdsburg Ave Healdsburg CA
Fully refundableReserve now, pay when you stay
The price is AU$654 per night from 14 June to 15 June
AU$654
14 June - 15 June
includes taxes & fees
With a stay at H2Hotel, you'll be centrally located in Healdsburg, steps from Healdsburg Plaza and within a 10-minute walk of Healdsburg Museum.
Opens in a new windowH2Hotel
Don't see what you're looking for?
See all available properties in Healdsburg
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.