Book Holiday Homes in Healdsburg

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Featured Holiday Homes in Healdsburg

Walk to Russian River - Casa Del Rio - Unit A

Walk to Russian River - Casa Del Rio - Unit A

Forestville
The price is NZ$613 per night from 27 Apr to 28 Apr
NZ$613
includes taxes & fees
27 Apr - 28 Apr
Stay at this vacation home in Forestville. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Russian River and Porter Creek Vineyards ...
Walk to Russian River - Casa Del Rio - Unit A
Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views

Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views

Guerneville
Stay at this vacation home in Guerneville. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Korbel Winery and Pee Wee Golf and ...
Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views
 Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country

Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country

Guerneville
Stay at this vacation home in Guerneville. Enjoy free WiFi, patios, and cable/satellite TV service. Our guests praise the helpful staff in our reviews. Popular ...
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country
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~Riverfront 3 Bed 2 Bath+ hot tub, private dock & watercraft. 3/4 mile to town~

~Riverfront 3 Bed 2 Bath+ hot tub, private dock & watercraft. 3/4 mile to town~

Guerneville
Stay at this vacation home in Guerneville. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Pee Wee Golf and Arcade and Johnson's ...
~Riverfront 3 Bed 2 Bath+ hot tub, private dock & watercraft. 3/4 mile to town~
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
Stay at this vacation home in Healdsburg. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Russian River and Windsor Oaks Vineyards ...
Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi
Wine Country Get Away

Wine Country Get Away

Windsor
Stay at this vacation home in Windsor. Enjoy free WiFi, a garden, and tennis courts. Popular attractions Russian River and Powell's Sweet Shoppe - Windsor are ...
Wine Country Get Away
5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley

5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley

Windsor
Book a stay at this family-friendly vacation home in Santa Rosa. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Russian River and ...
5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley
~ Main House + 3 Private Guest Cottages ~ Hot Tub ~ Pool ~ Pet Friendly ~

~ Main House + 3 Private Guest Cottages ~ Hot Tub ~ Pool ~ Pet Friendly ~

Guerneville
Stay at this vacation home in Guerneville. Enjoy free WiFi, private pools, and a garden. Popular attractions Johnson's Beach and Armstrong Redwoods State Park ...
~ Main House + 3 Private Guest Cottages ~ Hot Tub ~ Pool ~ Pet Friendly ~
Luxurious Large Home, Beautiful Pool, Extensive Gardens

Luxurious Large Home, Beautiful Pool, Extensive Gardens

Guerneville
Book a stay at this family-friendly vacation home in Guerneville. Enjoy free WiFi, private pools, and a garden. Popular attractions Johnson's Beach and Pee Wee ...
Luxurious Large Home, Beautiful Pool, Extensive Gardens
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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
247 Holiday Homes
Lowest Price
NZ$328
Highest Price
NZ$1,854
Popular accommodation
Walk to Russian River - Casa Del Rio - Unit A, Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views, Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country, ~Riverfront 3 Bed 2 Bath+ hot tub, private dock & watercraft. 3/4 mile to town~, Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi, Wine Country Get Away, 5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley, ~ Main House + 3 Private Guest Cottages ~ Hot Tub ~ Pool ~ Pet Friendly ~, Luxurious Large Home, Beautiful Pool, Extensive Gardens

Top trending hotels in Healdsburg

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 NZ$328 per night from 27 Apr to 28 Apr
NZ$328
includes taxes & fees
27 Apr - 28 Apr
Stay at this 3.5-star hotel in Healdsburg. Enjoy free WiFi, 2 hot tubs, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
The Lodge at Healdsburg, Tapestry Collection by Hilton
H2Hotel

H2Hotel

4 out of 5
219 Healdsburg Ave, Healdsburg, CA
Fully refundableReserve now, pay when you stay
The price is NZ$448 per night from 27 Apr to 28 Apr
NZ$448
includes taxes & fees
27 Apr - 28 Apr
Stay at this 4-star spa hotel in Healdsburg. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
H2Hotel
Montage Healdsburg

Montage Healdsburg

5 out of 5
100 Montage Way, Healdsburg, CA
Fully refundableReserve now, pay when you stay
The price is NZ$1,854 per night from 26 May to 27 May
NZ$1,854
includes taxes & fees
26 May - 27 May
Stay at this 5-star luxury hotel in Healdsburg. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
Montage Healdsburg
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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 NZ$359 per night from 11 May to 12 May
NZ$359
includes taxes & fees
11 May - 12 May
Stay at this 3-star business-friendly hotel in Healdsburg. Enjoy free breakfast, free WiFi, and a free area shuttle. Our guests praise the helpful staff and ...
Hotel Trio Healdsburg
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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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^Subject to availability and chosen travel dates.