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Browse Select Healdsburg Vacation Homes

Our top choices for Healdsburg vacation homes

Luxurious Large Home, Beautiful Pool, Extensive Gardens

9.8 out of 10, Exceptional, (153)
"We absolutely loved this spot for our engagement celebration. It housed us comfortably, provided all the necessities, and made it as fun as could be. Top notch"
Luxurious Large Home, Beautiful Pool, Extensive Gardens

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

8.4 out of 10, Very good, (28)
"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

Xanadu Healdsburg | Luxury Estate in Healdsburg

10.0 out of 10, Exceptional, (27)
"We really enjoyed the pool and family room!"
Xanadu Healdsburg | Luxury Estate in Healdsburg

Casa Pavone, by Vinifera Homes

10.0 out of 10, Exceptional, (7)
"Casa Pavone was beautiful inside and out. It is very spacious for you to spread out with your friends and family. We enjoyed sitting outside listening to the water in the stream next to the property. We had everything we needed and enjoyed the quiet setting. Thanks Harman for being there if we needed."
Casa Pavone, by Vinifera Homes

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 CA $152
CA $537 total
includes taxes & fees
Aug 27 - Aug 28
Walk to Russian River - Casa Del Rio - Unit A

Renovated Vineyard Home - 4 BR/4 BA - Solar Pool, Spa, Views

10.0 out of 10, Exceptional, (150)
"Wonderful house and yard. Manager is excellent as well. We love staying here"
Renovated Vineyard Home - 4 BR/4 BA - Solar Pool, Spa, Views

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

5 BEDROOM, 6.5 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE

10.0 out of 10, Exceptional, (194)
"We stayed here for husband’s birthday weekend. Beautiful property. It had everything we needed for a relaxing weekend away. "
5 BEDROOM, 6.5 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE

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

Private Luxury home in Healdsburg with Vineyard, Sauna, Hot tub, Tesla Charger

10.0 out of 10, Exceptional, (8)
"Stunning property! The perfect getaway for a girls weekend. "
Private Luxury home in Healdsburg with Vineyard, Sauna, Hot tub, Tesla Charger

~ 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 ~

~Riverfront 3 Bed 2 Bath + Hot Tub, Private Dock & Watercraft. 3/4 mile to town~

10.0 out of 10, Exceptional, (84)
"We loved our stay! "
~Riverfront 3 Bed 2 Bath + Hot Tub, Private Dock & Watercraft. 3/4 mile to town~

Valley Vista | Complimentary wine tasting at Croix Estate included!

10.0 out of 10, Exceptional, (79)
"Lovely house with everything needed for a wonderful stay. Truly a tree top paradise!"
Valley Vista | Complimentary wine tasting at Croix Estate included!

Lazy Bear: Near Guerneville! Lodge-Enchanting Cabin in a Forest!HtTb,WiFi,Pup

9.6 out of 10, Exceptional, (61)
"Enjoyed our stay. House was clean, well stocked and close to wineries, the golf course and quick drive to the coast. Loved relaxing in the hot tub. Would definitely stay here again if in the area. "
Lazy Bear: Near Guerneville! Lodge-Enchanting Cabin in a Forest!HtTb,WiFi,Pup

Wooded Restful Retreat, with broad scenic views, outdoor dining

10.0 out of 10, Exceptional, (313)
"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

Outside Inn-Newly Renovated, Open Layout, Large Yard, Walk to Beach, Spa, Kayaks

9.6 out of 10, Exceptional, (90)
"Not great curb appeal but very nice once inside. Multiple living spaces for a"
Outside Inn-Newly Renovated, Open Layout, Large Yard, Walk to Beach, Spa, Kayaks

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

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

Redwood River House--Complimentary wine tasting at Croix included!

9.4 out of 10, Exceptional, (63)
"Spent a few days here with some friends and their young children. The space was perfect for our visit and we loved the location!"
Redwood River House--Complimentary wine tasting at Croix included!

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!
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