Holiday Homes in Healdsburg

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Featured Holiday Homes in Healdsburg and around

Walk to Russian River - Casa Del Rio - Unit A

9.2 out of 10, Wonderful, (34)
"Great location to stay to get the most out of your wine trip. "
The price is €342
includes taxes & fees
18 Aug - 19 Aug
Walk to Russian River - Casa Del Rio - Unit A

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

Casa Pavone, by Vinifera Homes

10.0 out of 10, Exceptional, (7)
Casa Pavone, by Vinifera Homes

Luxurious Large Home, Beautiful Pool, Extensive Gardens

9.8 out of 10, Exceptional, (153)
"The property is stunning, the house has everything you need, the kitchen was fully equipped with every gadget required for a gourmet meal. The pool was amazing to have, the hot tub was a killer, the outdoor space was stunning. All in all an incredible experience. The costs do start to add up with pool heating, dogs, etc. so make sure to read the listing in its entirety before committing. The host was very communicative and respectful. Highly recommend this stay! "
Luxurious Large Home, Beautiful Pool, Extensive Gardens

Valley Vista | Complimentary wine tasting at Croix Estate included!

10.0 out of 10, Exceptional, (78)
"Lovely house with everything needed for a wonderful stay. Truly a tree top paradise!"
Valley Vista | Complimentary wine tasting at Croix Estate included!

Beautiful Bohemian Retreat

8.6 out of 10, Excellent, (42)
"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

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

9.8 out of 10, Exceptional, (16)
"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

Magnolia Ranch Vineyards | Historic house in Healdsburg with lovely private yard

10.0 out of 10, Exceptional, (12)
"Comfy beds, great location & views. 1 mile from town - very peaceful and nice sized 2 bedroom home. Perfect for a coupes wine tasting. "
Magnolia Ranch Vineyards | Historic house in Healdsburg with lovely private yard

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

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

Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown

10.0 out of 10, Exceptional, (256)
"Our group had a fantastic stay at this property. The location is amazing - minutes from downtown Healdsburg but just far enough to feel a bit secluded. Tons of great wineries nearby (I recommend De La Montanya)."
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown

Wooded Restful Retreat, with broad scenic views, outdoor dining

10.0 out of 10, Exceptional, (312)
"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, (15)
"We loved our stay at the place. It was clean, well-maintained, and well-stocked. It was perfect for our girls weekend. "
Retreat to Rise and Shine! Pool, Hot Tub, Walk to Drake's Beach! Game Room!

Xanadu Healdsburg | Luxury Estate in Healdsburg

10.0 out of 10, Exceptional, (26)
"We really enjoyed the pool and family room!"
Xanadu Healdsburg | Luxury Estate in Healdsburg

Vineyards Edge - Pool, Hot Tub, Bikes, Pets Welcome, Fire Pit- 1mi to Downtown

10.0 out of 10, Exceptional, (11)
"This was one of the most incredible VRBOs I have ever stayed at. Far exceeded every expectation and the hosts were so nice and communicative."
Vineyards Edge - Pool, Hot Tub, Bikes, Pets Welcome, Fire Pit- 1mi to Downtown

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

Wood Chalet:Peaceful,Modern Vibe! Contemporary Cabin in Redwoods! HtTb/WiFi!

9.8 out of 10, Exceptional, (30)
"The 3 of us loved all the room, hot tub, ease of access and proximity to everything. Highly recommend!"
Wood Chalet:Peaceful,Modern Vibe! Contemporary Cabin in Redwoods! HtTb/WiFi!

✨River View Lodge | Tasting at Croix included!

9.6 out of 10, Exceptional, (70)
"The property is perfectly located just 10 minutes from central Healdsburg. Great for wine tasting and family time. "
✨River View Lodge | Tasting at Croix included!

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

9.8 out of 10, Exceptional, (35)
"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 ~
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