Search Vacation Homes in Healdsburg
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Our top choices for Healdsburg vacation homes
Vacation Home in Forestville
Walk to Russian River - Casa Del Rio - Unit A9.2 out of 10, Wonderful, (38)
"Would definitely go back"
liz n.
$372 nightly
The price is $385
Dec 14 - Dec 15
Total with taxes and fees
Vacation Home in Guerneville
Cozy Riverfront Cabin - Beach Access & Wood Stove9.8 out of 10, Exceptional, (12)
"Wonderful location and had everything we needed! "
Maryrose H.
$442 nightly
The price is $497
Dec 14 - Dec 15
Total with taxes and fees
Vacation Home in Northwest Santa Rosa
Russian River Brew-cation Home10.0 out of 10, Exceptional, (55)
"My family of 6 adults enjoyed this lovely home. It was as advertised and there were even little extras like labels and notes to find things, a basket of necessities in case we forgot something, and everything you could think of to make us feel comfortable and at home. Thank-you!!"
Sherrie R.
$403 nightly
The price is $442
Dec 15 - Dec 16
Total with taxes and fees
Vacation Home in Northwest Santa Rosa
Winemaker's Delight: 3BD/3BA Russian River Valley9.8 out of 10, Exceptional, (72)
"Comfortable beds and clean place. We enjoyed it"
Amy F.
$401 nightly
The price is $440
Dec 12 - Dec 13
Total with taxes and fees
Vacation Home in Northwest Santa Rosa
Sonoma Getaway: Winemaker’s Home with Modern Amenities10.0 out of 10, Exceptional, (77)
"The house was very clean and cozy in a cute neighborhood. Very nice backyard space and interior, would definitely recommend and stay again."
Gary R.
$412 nightly
The price is $452
Jan 4 - Jan 5, 2026
Total with taxes and fees
Vacation Home in Northwest Santa Rosa
Wineries & Wine: A Comforting Getaway in Wine Country9.4 out of 10, Exceptional, (22)
"This is a great location, and comfortable space for us to tour wine country! We enjoyed the condo, it was quite and clean."
Gayle C.
$355 nightly
The price is $389
Jan 5 - Jan 6, 2026
Total with taxes and fees
Vacation Home in Healdsburg
Vineyard Oasis: Luxury Home in the Heart of Sonoma.10.0 out of 10, Exceptional, (7)
"We had a great time!The house was perfect for our needs!"
Theresa C.
$359 nightly
The price is $397
Jan 4 - Jan 5, 2026
Total with taxes and fees
Vacation Home in Healdsburg
Heron House | Wine Tastings Included10.0 out of 10, Exceptional, (26)
"Loved this house for a weekend getaway. We loved taking advantage of the deck, grill, and river access. Short drive to the town square and wineries."
Maria D.
$860 nightly
The price is $970
Dec 27 - Dec 28
Total with taxes and fees
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.
Top Healdsburg Hotel Reviews
Fairview Inn and Suites
10/10 Excellent
Find out more about Healdsburg
Healdsburg Vacation Homes information
Number of reviews | 558 |
|---|---|
Accommodation | 231 Vacation Homes |
Lowest Price | $216 |
Highest Price | $2,254 |
Explore a world of travel with Expedia
- Hotels near Healdsburg Plaza
- Hotels near Healdsburg Center for the Arts
- Hotels near Raven Performing Arts Theater
- Hotels near Pezzi King Winery
- Hotels near Tayman Park Golf Course
- Hotels near Healdsburg Golf Club
- Hotels near Krug Event Center
- Hotels near Simi Winery
- Hotels near Healdsburg Ridge Open Space Preserve
- Hotels near Matrix Winery
- Hotels near Wilson Winery
- Hotels near Windsor Oaks Vineyards
- Hotels near Mazzocco Winery
- Hotels near Russian River
- Hotels near Dry Creek Vineyard
- Condo Rentals in Windsor
- Resorts in Windsor
- B&B in Windsor
- Cabin Rentals in Windsor
- Motels in Windsor
- Condo Resorts in Windsor
- Vacation Homes in Windsor
- Castles in Windsor
- Villas in Windsor
- Windsor Hotels
- Hotels near Francis Ford Coppola Winery
- Hotels near Trentadue Winery
- Hotels near Starlite Vineyards
- Hotels near Soda Rock Winery
- Cheap Hotels in Windsor
- Hotels near Dom Whitney Tasting Lounge
- Hotels near Powell's Sweet Shoppe - Windsor
- 4 Star Hotels in Windsor
- Pet-friendly Hotels in Windsor
- Romantic Hotels in Windsor
- Resorts & Hotels with Spas in Windsor
- Winery Hotels in Windsor
- Best Western Hotels in Windsor
- Motel 6 Hotels in Windsor
- Hotels with Restaurants in Windsor
- Casino Hotels in Windsor
- 3 Star Hotels in Windsor
- Marriott Hotels & Resorts in Windsor
- Hotels with Kitchenettes in Windsor
- Hotels with Free Breakfast in Windsor
- Extended Stay Hotels in Windsor
- 5 Star Hotels in Windsor
- Hotel Wedding Venues Hotels in Windsor
- Luxury Hotels in Windsor
- Gay friendly Hotels in Windsor
- All-inclusive Resorts in Windsor
- Hotels with an Outdoor Pool in Windsor
- Family Hotels in Windsor
- Hotels with Laundry Facilities in Windsor
- Hotels with Fireplaces in Windsor
- Hotels with Suites in Windsor
- Golf Hotels in Windsor
- Hotels with Balconies in Windsor
- Flights to Windsor
- Flights from Windsor
- Flights from San Bernardino to Windsor
- Flights from Phoenix to Windsor
- Flights from Southampton to Windsor
- Flights from Burlington to Windsor
- Flights from Luxembourg City to Windsor
- Flights from Grand Island to Windsor
- Flights from Great Falls to Windsor
- Flights from Cedar Rapids - Iowa City to Windsor
- Flights from El Cajon to Windsor
- Flights from Elliot Lake to Windsor
- Flights from Alamosa to Windsor
- Healdsburg Plaza
- Healdsburg Museum
- Raven Performing Arts Theater
- Pezzi King Winery
- Krug Event Center
- Simi Winery
- Matrix Winery
- Windsor Oaks Vineyards
- Mazzocco Winery
- Dry Creek Vineyard
- Francis Ford Coppola Winery
- Trentadue Winery
- Starlite Vineyards
- Soda Rock Winery
- Dom Whitney Tasting Lounge
- Powell's Sweet Shoppe - Windsor
- Visit Windsor
- Windsor Vacations
- Car rentals near Healdsburg Plaza
- Car rentals near Raven Performing Arts Theater
- Car rentals near Krug Event Center
- Car rentals near Matrix Winery
- Sportscar Car Rentals near Matrix Winery
- Car rentals near Dry Creek Vineyard
- Car rentals near Russian River
- Car rentals near Francis Ford Coppola Winery
- Car rentals near Windsor