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Compare 248 Vacation Homes in Healdsburg with updated reviews, rates, and availability.

Luxurious Large Home, Beautiful Pool, Extensive Gardens

9.8 out of 10, Exceptional, (147)
"Spent a weekend here with family and friends. The vacation home is beautiful and very tastefully done! Offers spectacular views from front yard and backyard, and lots of entertainment with the game room and swimming pool. David is a warm and welcoming host, very easy to communicate with. We had a great time, and would definitely recommend this vacation home to those visiting the area!"
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, (24)
"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

Valley Vista: Redwoods Retreat w/ Hot Tub, Deck & Views

10.0 out of 10, Exceptional, (77)
"The place was beautiful! Surrounded by Redwood Trees and nestled on a quiet road. Well worth it!"
Valley Vista: Redwoods Retreat w/ Hot Tub, Deck & Views

GuernevilleGetaway:Lounge,GmRm,Redwoods, HotTub, Pup, WiFi! Super Chill Home

10.0 out of 10, Exceptional, (21)
"Loved this place, had a great time with my partner and the area is just awesome. "
GuernevilleGetaway:Lounge,GmRm,Redwoods, HotTub, Pup, WiFi! Super Chill Home

Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg

10.0 out of 10, Exceptional, (30)
"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

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

9.6 out of 10, Exceptional, (11)
"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

Walk to Russian River - Casa Del Rio - Unit A

9.2 out of 10, Wonderful, (30)
"Only stayed one night for a family get together at another residence. House was exactly as expected and met our needs. Beds were clean, comfortable and made for a good nights sleep. Location is close to the river in a quiet neighborhood. Would stay again the next time we're in town. "
The price is AED 400
AED 1,345 total
includes taxes & fees
8 Jun - 9 Jun
Walk to Russian River - Casa Del Rio - Unit A

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

10.0 out of 10, Exceptional, (5)
"Stunning property, great communication with Sarah and her property manager Nicole "
Private Luxury home in Healdsburg with Vineyard, Sauna, Hot tub, Tesla Charger

Melody Vineyard Cottage

10.0 out of 10, Exceptional, (1)
"Great place for a couple for a getaway."
Melody Vineyard Cottage

Vinehaven - 3BD Healdsburg Retreat with Spa

10.0 out of 10, Exceptional, (1)
"We had a lovely stay at Vinehaven as we explored Sonoma County. Thanks so much!"
Vinehaven - 3BD Healdsburg Retreat with Spa

Charming house in Healdsburg with Pool and Hot Tub

Charming house in Healdsburg with Pool and Hot Tub

Wine Country Home of Healdsburg Wine Maker

9.4 out of 10, Exceptional, (20)
"What a wonderful place to call home while on vacation!!!! Cynthia and staff are amazing and added so much to our stay. Make sure you experience the Barn tasting…it was the highlight of our trip. Property is exactly as described and the location is perfect. "
The price is AED 1,770
AED 3,261 total
includes taxes & fees
2 Jul - 3 Jul
Wine Country Home of Healdsburg Wine Maker

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

10.0 out of 10, Exceptional, (163)
"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

Wine Country Get Away

9.8 out of 10, Exceptional, (29)
"Great location especially for proximity to our family. So enjoyed being able to have our family over for dinner. our"
The price is AED 621
AED 1,394 total
includes taxes & fees
3 Jun - 4 Jun
Wine Country Get Away

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

2.0 star property
8.0 out of 10, Very Good, (1)
"Comfortable and cozy. We were told in the guidebook not to use the wood burning stove as it was under construction. It was indeed ready for use after a brief call to management. There was no instructions for how to use it. We decided against it. The electronic Gate lock for entry wasn’t always working. The refrigerator is newish but beat up inside. Broken drawers and missing shelves.Otherwise, it’s a nice. Little place to stay."
Stylish, Private, Sunny Spot close to Everything - Excellent Location!

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

9.8 out of 10, Exceptional, (28)
"Great property with plenty of room for family gathering and privacy with lots of sleeping areas. "
~ Main House + 3 Private Guest Cottages ~ Hot Tub ~ Pool ~ Pet Friendly ~

Cozy Riverfront Cabin - Beach Access & Wood Stove

9.2 out of 10, Wonderful, (5)
"Nice rustic place, redwoods and river are in the back yard!! Host are very helpful and extremely quick to answer any questions you might have during your stay. Will definitely be back again"
The price is AED 573
AED 1,861 total
includes taxes & fees
10 Jun - 11 Jun
Cozy Riverfront Cabin - Beach Access & Wood Stove

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

10.0 out of 10, Exceptional, (58)
"Our second stay at the property. Will be back again!"
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

𝑳𝒖𝒙𝒖𝒓𝒚 𝑷𝒓𝒊𝒗𝒂𝒕𝒆 𝑬𝒔𝒕𝒂𝒕𝒆 𝒂𝒕 𝒁𝒐𝒆𝒍𝒍𝒂 𝑽𝒊𝒏𝒆𝒚𝒂𝒓𝒅.𝑷𝑶𝑶𝑳&𝑺𝑷𝑨!𝑮𝑨𝑴𝑬𝑹𝑶𝑶𝑴!

9.6 out of 10, Exceptional, (61)
"I had a group of 10 people staying at Zoella Vineyard for my birthday and the place was so perfect for us. The house was massive and had tons of amenities and games. The pool and hot tub were awesome too! If you have a big group and want to enjoy the beautiful Sonoma in a gorgeous house, this is the place to be!"
The price is AED 3,673
AED 6,079 total
includes taxes & fees
3 Jun - 4 Jun
𝑳𝒖𝒙𝒖𝒓𝒚 𝑷𝒓𝒊𝒗𝒂𝒕𝒆 𝑬𝒔𝒕𝒂𝒕𝒆 𝒂𝒕 𝒁𝒐𝒆𝒍𝒍𝒂 𝑽𝒊𝒏𝒆𝒚𝒂𝒓𝒅.𝑷𝑶𝑶𝑳&𝑺𝑷𝑨!𝑮𝑨𝑴𝑬𝑹𝑶𝑶𝑴!

4BD/4BA Heated Pool+Spa+Sonos+8 beds: 11min Healdsburg & Alexander Valley

9.8 out of 10, Exceptional, (28)
"We spent Thanksgiving week at the home. Description of property is good. Lots of space for families to gather. Good access to groceries in Santa Rosa , good restaurants and wine tours. Outdoor space is ample "
4BD/4BA Heated Pool+Spa+Sonos+8 beds: 11min Healdsburg & Alexander Valley
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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