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Vacation Homes in Healdsburg

Dog-friendly home with AC, walk to downtown Guerneville & Johnson's Beach

9.6 out of 10, Exceptional, (12)
"The home was quite and comfortable. Easy walk to a lovely town, and lots of great wineries and eateries with live entertainment. "
Dog-friendly home with AC, walk to downtown Guerneville & Johnson's Beach

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

8.4 out of 10, Very Good, (25)
"This place was so ideal. Beautiful outdoor area, plenty of room for socializing as well as privacy. So great!"
Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views

Gorgeous Views, Pool and Hot Tub, 12 mins to HB Plaza

10.0 out of 10, Exceptional, (166)
"Fantastic and relaxing stay. Beautiful views, comfortable home, peaceful surroundings. Always an excellent place to recharge. "
Gorgeous Views, Pool and Hot Tub, 12 mins to HB Plaza

Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg

10.0 out of 10, Exceptional, (32)
"Absolutely wonderful stay. The house was beautiful and clean, with multiple spacious common areas for family time. The Limerick Lane team was also incredibly communicative and accommodating throughout. 100% recommend."
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg

Cozy Riverfront Cabin - Beach Access & Wood Stove

9.6 out of 10, Exceptional, (7)
"Cozy cottage, communicative hosts"
The price is SAR 596
SAR 1,970 total
includes taxes & fees
16 Jul - 17 Jul
Cozy Riverfront Cabin - Beach Access & Wood Stove

Beautiful Bohemian Retreat

8.6 out of 10, Excellent, (40)
"The decor was clearly thought out and created a real Bohemian feel which was just so charming for a little place nestled in the trees. Loved the bedroom configuration with one bedroom on the main level and the 2 down below. Our room on the main level had a big skylight which allowed us to see the moon and trees above us while in bed which was romantic. The living room and kitchen have a lot of unique pieces and paintings and was well stocked with the essentials. The manager was very responsive...
Beautiful Bohemian Retreat

Heart of Wine Country, Cute Cottage w/Hot Tub

9.8 out of 10, Exceptional, (26)
"We enjoyed our stay in this home although it was very brief. A great location in Windsor. "
The price is SAR 1,097
SAR 2,200 total
includes taxes & fees
16 Jul - 17 Jul
Heart of Wine Country, Cute Cottage w/Hot Tub

Cozy & Stylish Cottage w/Hot Tub, Free WiFi, Private Washer/Dryer, & Gas Grill

8.8 out of 10, Excellent, (9)
"Comfortable place and tastefully decorated!"
Cozy & Stylish Cottage w/Hot Tub, Free WiFi, Private Washer/Dryer, & Gas Grill

Stylish, Private, Sunny Spot close to Everything - Excellent Location!

2.0 star property
9.0 out of 10, Wonderful, (2)
"Being surrounded by trees was by far the best thing about this place. Huge deck to play games on, sit by the pool (the pool was pretty chilly the whole time, but felt nice when it was so hot out). We had such a great time. "
Stylish, Private, Sunny Spot close to Everything - Excellent Location!

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

10.0 out of 10, Exceptional, (62)
"Great stay, recommend in every way"
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

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

9.8 out of 10, Exceptional, (32)
"Great property with plenty of room for family gathering and privacy with lots of sleeping areas. "
~ Main House + 3 Guest Cottages ~ Hot Tub ~ Pool ~ EV Charger ~ Pet Friendly ~

Relaxing retreat in the redwoods-not recommended for partiers..

9.8 out of 10, Exceptional, (144)
"Loved this place! Had everything you could want or need, comfy beds, stuff to cook with, a hot tub and beautiful scenery to boot. Definitely recommend! "
Relaxing retreat in the redwoods-not recommended for partiers..

Wine country home base with dog-friendly fenced yard & alfresco patio

8.0 out of 10, Very Good, (9)
"Very welcoming and relaxing experience. Would definitely recommend!"
Wine country home base with dog-friendly fenced yard & alfresco patio

Sonoma Wine County Oasis: King | BBQ | Fire Pit

10.0 out of 10, Exceptional, (1)
"Very nice property in a very quiet neighborhood."
Sonoma Wine County Oasis: King | BBQ | Fire Pit

Wooded Restful Retreat, with broad scenic views, outdoor dining

10.0 out of 10, Exceptional, (308)
"Property is spotless. View is spectacular. Central location to restaurants and vineyards. Host was friendly and helpful! Highly recommend this property. "
Wooded Restful Retreat, with broad scenic views, outdoor dining

Vineyard View. Main house + Swimming Pool; a Resort Feel in a Vineyard Setting!

10.0 out of 10, Exceptional, (32)
"Fabulous property with many amenities. Pool, lovely well equipped kitchen outstanding location."
Vineyard View. Main house + Swimming Pool; a Resort Feel in a Vineyard Setting!

Dog-friendly cabin under towering redwoods w/expansive deck, bbq & hot tub

8.6 out of 10, Excellent, (4)
"It was a gorgeous home that felt quite remote. The hot tub was very nice aswell as the cookware and amenities. My only complaint is the road there is very narrow barely fitting my Toyota tundra. If you miss the cabin and go past it there’s not many places to turn around and leads to an unpaved road otherwise it is absolutely something I would recommend just keep your eye out along that road for the lazy bear sign to not go too far."
Dog-friendly cabin under towering redwoods w/expansive deck, bbq & hot tub

Retreat to Rise and Shine! Pool, Hot Tub, Walk to Drake's Beach! Game Room!

9.4 out of 10, Exceptional, (13)
"The house was clean, the tub was hot, and the game room was a hit! Thank you so much for sharing your beautiful home with us!"
Retreat to Rise and Shine! Pool, Hot Tub, Walk to Drake's Beach! Game Room!

Villa Eileen: Riverfront Gem w/ Outdoor Kitchen & Private Beach

8.8 out of 10, Excellent, (16)
"Perfect Russian River home for my wife and my parents."
Villa Eileen: Riverfront Gem w/ Outdoor Kitchen & Private Beach

Wine Country Estate Home

2.0 star property
9.2 out of 10, Wonderful, (5)
"Very enjoyable and very close to great wineries and Healdsburg "
Wine Country Estate Home
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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