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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, (15)
"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, (27)
"Cute cottage. The outdoor chairs in front were very old and worn out. The furniture by the hot tub was dirty from being under the trees but we used one of the sheets and it was fine. was dirty"
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, (168)
"Lovely setting. Cant wait to return!"
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, (34)
"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"
Cozy Riverfront Cabin - Beach Access & Wood Stove

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

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

Heart of Wine Country, Cute Cottage w/Hot Tub

9.4 out of 10, Exceptional, (27)
"We enjoyed our stay in this home although it was very brief. A great location in Windsor. "
Heart of Wine Country, Cute Cottage w/Hot Tub

Beautiful Bohemian Retreat

8.6 out of 10, Excellent, (41)
"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

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

2.0 star property
9.4 out of 10, Exceptional, (3)
"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, (63)
"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, (33)
"The main house (2 bedroom/2 bath) and the 3 bungalows (each with a bed/bath) were perfect for the 5 couples in our group. We all loved our stay will go back! "
~ 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, (145)
"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..

Rivers Breeze | Complimentary wine tasting at Croix included!

10.0 out of 10, Exceptional, (14)
"In Healdsburg to visit family and could not have had a more comfortable and lovely place to stay! It was impeccably clean, well located and so cute! We loved it!"
Rivers Breeze | Complimentary wine tasting at Croix included!

Wooded Restful Retreat, with broad scenic views, outdoor dining

10.0 out of 10, Exceptional, (310)
"The VRBO was exactly as described. Communication with Cynthia was fast and she answered all of our questions. The beds were super comfortable and place was spotless and exactly as described. Would definitely stay again!"
Wooded Restful Retreat, with broad scenic views, outdoor dining

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

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

9.4 out of 10, Exceptional, (14)
"Had a great time. 1st time stay in the area and it was a blast. Close to river and short drive to ocean. The house had great amenities for my teenage daughter and her friends. Very pleased with the overall trip. "
Retreat to Rise and Shine! Pool, Hot Tub, Walk to Drake's Beach! Game Room!

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

8.8 out of 10, Excellent, (5)
"Although it was raining during our stay, looking out the windows at the mossy trees was magical. The temp of the cabin when we checked in was a freezing 50 degrees! It would have been nice for it to be somewhat warmer. Having said that, the place warmed up super fast and stayed warm. We cooked almost all our meals at the cabin so we would have liked a few more pans. The place was very clean with an abundance of clean towels, pillows and blankets. The deck is lovely and would be great to spend...
Dog-friendly cabin under towering redwoods w/expansive deck, bbq & hot tub

Cypress House & Studio, Walk to Healdsburg Plaza by RedAwning

9.8 out of 10, Exceptional, (26)
"This place was super convenient and spacious. Easy walk to plenty of Healdsburg restaurants and shops. The only minus was the early morning garbage trucks noise. But that was minor. "
Cypress House & Studio, Walk to Healdsburg Plaza by RedAwning

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

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

10.0 out of 10, Exceptional, (33)
"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!
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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Top Healdsburg Hotel Reviews