Healdsburg Vacation Rentals
Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Browse Select Healdsburg Vacation Homes
Riverfront, dog-friendly home with private hot tub, fireplaces & amazing decks
Riverfront, dog-friendly home with private hot tub, fireplaces & amazing decks
8.0 out of 10, Very good, (7)
Valley Vista- Forest bungalow with valley views, dog friendly and hot tub!
Valley Vista- Forest bungalow with valley views, dog friendly and hot tub!
10.0 out of 10, Exceptional, (58)
Dog-friendly home with firepit, Hot tub, woodstove & 2 decks - walk to beach
Dog-friendly home with firepit, Hot tub, woodstove & 2 decks - walk to beach
9.8 out of 10, Exceptional, (11)
Save an average of 15% on thousands of hotels when you're signed in
Beautiful 4 bedroom home w/ luxurious furnishings
Beautiful 4 bedroom home w/ luxurious furnishings
9.4 out of 10, Exceptional, (15)
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country
10.0 out of 10, Exceptional, (89)
Private Vineyard Haven--walk to the HBG Square!
Private Vineyard Haven--walk to the HBG Square!
9.8 out of 10, Exceptional, (38)
Guerneville Getaway: Craftsman Retreat! Fun! GameRoom! Hot Tub! Near Wineries
Guerneville Getaway: Craftsman Retreat! Fun! GameRoom! Hot Tub! Near Wineries
9.4 out of 10, Exceptional, (3)
Cottage home near the Russian River; county parks; numerous wineries
Cottage home near the Russian River; county parks; numerous wineries
10.0 out of 10, Exceptional, (78)
Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views
Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views
7.6 out of 10, Good, (8)
Stunning Views🌲Pet-Friendly🐶 Kayaks avail🚣♀️ Semi-Private Beach🏖Lux Spa
Stunning Views🌲Pet-Friendly🐶 Kayaks avail🚣♀️ Semi-Private Beach🏖Lux Spa
9.6 out of 10, Exceptional, (157)
Windsor Wine Country Vacation Home
Windsor Wine Country Vacation Home
9.6 out of 10, Exceptional, (87)
Santa Rosa Serenity: Cozy 1bd Perch Amidst Wine Country
Santa Rosa Serenity: Cozy 1bd Perch Amidst Wine Country
9.4 out of 10, Exceptional, (12)
The price is CA $148
CA $446 total
includes taxes & fees
May 28 - May 29
4 Couple or 2/3 Families, Private w/Fantastic location, Views + Pool + Hot Tub
4 Couple or 2/3 Families, Private w/Fantastic location, Views + Pool + Hot Tub
9.8 out of 10, Exceptional, (46)
Lazy Bear Lodge- Enchanting Upscale Cabin! Cozy!Private!HotTub!Decks!PupOk!
Lazy Bear Lodge- Enchanting Upscale Cabin! Cozy!Private!HotTub!Decks!PupOk!
9.6 out of 10, Exceptional, (36)
Luxurious Wine Country Estate
Luxurious Wine Country Estate
10.0 out of 10, Exceptional, (1)
Wooded Restful Retreat, with broad scenic views, outdoor dining
Wooded Restful Retreat, with broad scenic views, outdoor dining
10.0 out of 10, Exceptional, (278)
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat
10.0 out of 10, Exceptional, (15)
Villa Eileen: Riverfront Gem w/ Outdoor Kitchen & Private Beach
Villa Eileen: Riverfront Gem w/ Outdoor Kitchen & Private Beach
9.4 out of 10, Exceptional, (8)
Outside Inn-Newly Renovated, Open Layout, Large Yard, Walk to Beach, Spa, Kayaks
Outside Inn-Newly Renovated, Open Layout, Large Yard, Walk to Beach, Spa, Kayaks
9.6 out of 10, Exceptional, (80)
NEW! Local Winemaker's 6 BDRM & VIP Wine Tasting!
NEW! Local Winemaker's 6 BDRM & VIP Wine Tasting!
9.6 out of 10, Exceptional, (13)
The price is CA $275
CA $725 total
includes taxes & fees
May 28 - May 29
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.
Other property types in Healdsburg
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
10.0 out of 10, Exceptional, (148)
Stunning Views🌲Pet-Friendly🐶 Kayaks avail🚣♀️ Semi-Private Beach🏖Lux Spa
Stunning Views🌲Pet-Friendly🐶 Kayaks avail🚣♀️ Semi-Private Beach🏖Lux Spa
9.6 out of 10, Exceptional, (157)
Chalk Hill Cottage Close to Wineries
Chalk Hill Cottage Close to Wineries
10.0 out of 10, Exceptional, (12)
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 Vacation Homes information
Number of reviews | 981 |
---|---|
Accommodation | 216 Vacation Homes |
Lowest Price | CA $148 |
Highest Price | CA $275 |
Recent Reviews in HealdsburgExpedia verified reviews
5/5 Excellent
A Fantastic Place in Dry Creek
"We love staying at this property in Dry Creek! It is so clean and has everything you'd want.. the location is perfect, right in the middle of everything Dry Creek and Healdsburg."
A verified traveller from San Rafael, California stayed at Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
Posted 3 days ago
Top Vacation Homes in Other Destinations
More Accommodation Types in Healdsburg
All Accommodation Types
Be inspired: Top Vacation Homes destinations in 2024
- Orlando Vacation Homes
- Florida Vacation Homes
- Kissimmee Vacation Homes
- Hawaii Vacation Homes
- Costa Rica Vacation Homes
- Walt Disney World® Vacation Homes
- Palm Springs Vacation Homes
- Naples Vacation Homes
- Victoria Vacation Homes
- Kelowna Vacation Homes
- Toronto Vacation Homes
- Las Vegas Vacation Homes
- Vancouver Vacation Homes
- Mexico Vacation Homes
- Phoenix Vacation Homes
- Fort Lauderdale Vacation Homes
- Davenport Vacation Homes
- Myrtle Beach Vacation Homes
- Los Angeles Vacation Homes
- Cape Coral Vacation Homes