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

Walk to Russian River - Casa Del Rio - Unit A

9.4 out of 10, Exceptional, (28)
"Our family of three enjoyed our stay and had plenty of space. We received all the check-in information ahead of time and management was very responsive with inquiries. We found the location to be great. Unfortunately, it rained a lot the first few days of our stay and we did not get to enjoy the Russian River as planned. But the river is a short walk away. This unit is on the 3rd floor which may be a challenge for seniors. We didn't spend much time outside the house due to the rain, aside from...
The price is SAR 375
SAR 1,313 total
includes taxes & fees
20 Apr - 21 Apr
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, (22)
"Our stay was overall really good.We did get a very wet weekend and we didn't know that to go from the kitchen to the rooms/bathroom we had to pass through the open patio, so we'd get wet and the floor got soaked as we came in and out.Other than that we had a lovely stay! The hot tub worked well, we watched DVDs and were able to prepare all our meals.I'd definitely come back."
Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views

Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country

10.0 out of 10, Exceptional, (123)
"Very nice riverfront property in a quiet neighborhood near Guerneville on the Russian River. View of the river off the back deck was quite scenic and the hot tub was an added pleasure.The interior was modern , clean and met all our needs. The drive to Santa Rosa was a bit longer than we’d like (About 30 minutes) but we got used to it. We would stay again if we go back to Sonoma county."
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country

~Riverfront 3 Bed 2 Bath+ hot tub, private dock & watercraft. 3/4 mile to town~

10.0 out of 10, Exceptional, (73)
"The house was really big and clean. The hot tub was hot and the view amazing. We loved watching the otters go by and the ducks and birds play in the river. Will be back when the river is slow and low so we can enjoy in the water activities. "
~Riverfront 3 Bed 2 Bath+ hot tub, private dock & watercraft. 3/4 mile to town~

Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi

10.0 out of 10, Exceptional, (14)
"Great place!! "
Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi

The Sonoma Valley Cottage

10.0 out of 10, Exceptional, (12)
"Great home and highly recommend this house. Very clean and comfy home."
The price is SAR 1,473
SAR 2,688 total
includes taxes & fees
19 Apr - 20 Apr
The Sonoma Valley Cottage

Wine Country Get Away

9.8 out of 10, Exceptional, (26)
"We enjoyed our stay at this property. The location is quiet, yet fairly close to stores and restaurants. The beds are soft but comfortable and the living room accommodated the 2 of us quite well. Kitchen had what we needed. It was nice to sit in the backyard. I do wish the lighting in the bedrooms and second bathroom was brighter. "
The price is SAR 634
SAR 1,657 total
includes taxes & fees
19 Apr - 20 Apr
Wine Country Get Away

5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley

9.8 out of 10, Exceptional, (25)
"We had 8 people in our group and the house was perfect. The house and backyard are amazing. Looking forward to coming back and staying here again. "
5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley

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

9.8 out of 10, Exceptional, (24)
"We had a 10 person retreat and the place was great combination of facilities and privacy. There is a cozy living room, large dining table, and two outside areas for meeting space. And the hot tub is a fantastic way for offline bonding. Rooms are fastidiously clean. There were a few problems with the property (unavoidable pool maintenance) and the management was highly communicative and accommodating. I can't recommend this place enough! "
~ Main House + 3 Private Guest Cottages ~ Hot Tub ~ Pool ~ Pet Friendly ~

Luxurious Large Home, Beautiful Pool, Extensive Gardens

9.8 out of 10, Exceptional, (142)
"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

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

Farpoint: Heated Infinity Pool, Mountain Views

10.0 out of 10, Exceptional, (6)
"Great location with lots of amenities. Very calming atmosphere. Very attentive staff. Can’t wait to go back."
Farpoint: Heated Infinity Pool, Mountain Views

Winemaker's Delight: 3BD/3BA Russian River Valley

9.8 out of 10, Exceptional, (55)
"Easily accessible VRBO from the freeway made our stay in Santa Rosa perfect. We had appointments in Healdsburg, SR and SF so the location was centrally located, making it ideal for us. Clean and comfortable- we’d stay again!"
Winemaker's Delight: 3BD/3BA Russian River Valley

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

10.0 out of 10, Exceptional, (3)
"We loved everything about our stay. The pre-trip communications were great and the home was perfectly suited for our family vacation in wine country. The location is ideal - close to the plaza, while still having easy access to excellent countryside roads. We wouldn't hesitate to stay there again."
Private Luxury home in Healdsburg with Vineyard, Sauna, Hot tub, Tesla Charger

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

9.6 out of 10, Exceptional, (59)
"Great house. Great host! "
The price is SAR 3,186
SAR 5,673 total
includes taxes & fees
21 Apr - 22 Apr
February SPECIAL 𝑳𝒖𝒙𝒖𝒓𝒚 𝑷𝒓𝒊𝒗𝒂𝒕𝒆 𝑬𝒔𝒕𝒂𝒕𝒆 𝒂𝒕 𝒁𝒐𝒆𝒍𝒍𝒂 𝑽𝒊𝒏𝒆𝒚𝒂𝒓𝒅.𝑷𝑶𝑶𝑳&𝑺𝑷𝑨!𝑮𝑨𝑴𝑬𝑹𝑶𝑶𝑴!

Fitch Mtn Lookout- Gorg & Comfy!Pets-Walkable Russian River-Spa under the stars!

9.6 out of 10, Exceptional, (166)
"Cool cabin, lots of communication with host. Hummingbirds were amazing, there were hundreds. Didn’t realize both bathrooms were on the lowest floor so the top floor bedroom had a two story walk down when facilities were needed. Roads are extremely narrow to get to house and we were expecting an easier route to the river. Great spot for folks looking for an “off the beaten path” stay. Treehouse feeling was great."
Fitch Mtn Lookout- Gorg & Comfy!Pets-Walkable Russian River-Spa under the stars!

Walk to Russian River - Casa del Rio - Unit B

9.6 out of 10, Exceptional, (14)
"The place was clean, quiet, and comfortable. It was nice to come back to in the evening. It was located well for the things we do: wine, woods, ocean, and food. "
Walk to Russian River - Casa del Rio - Unit B

Renovated farmhouse with vineyard views, bocce ball court, Ping-Pong, basketball

10.0 out of 10, Exceptional, (10)
"Everything about this property was outstanding! Spotless, well equipped, comfortable, spacious, indoor and outdoor relaxation areas, easy access to the freeway while being tucked away in the vineyard, bocce, ping pong, ample outdoor seating. We were blown away! Every detail was thought of and provided. We loved the natural light throughout. Comfortable beds and plenty of linens. This will be our home away from home when we visit Sonoma County!"
Renovated farmhouse with vineyard views, bocce ball court, Ping-Pong, basketball

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

9.6 out of 10, Exceptional, (86)
"Quiet location and plenty of space. We went in the winter but the backyard would be ideal in the summer months with close access to the river. We did enjoy the hot tub. If you are willing, it’s an easy two mile walk into town. Our host was very attentive and easy to communicate with. Thank you!"
Outside Inn-Newly Renovated, Open Layout, Large Yard, Walk to Beach, Spa, Kayaks

Private Vineyard Haven--walk to the HBG Square!

9.8 out of 10, Exceptional, (55)
"The house was exactly as described. Lovely home and garden area. Perfect location to explore Healdsburg and surrounding area"
Private Vineyard Haven--walk to the HBG Square!
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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Other property types in Healdsburg

✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨

10.0 out of 10, Exceptional, (287)
"Amazing cabin. Great location. We had an amazing 2nd time in this little paradise!"
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨

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

10.0 out of 10, Exceptional, (241)
"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, (300)
"The house,view, communications and cleanliness were exactly as promised—excellent. We felt welcomed and at home. With the information Cynthia provided, we did everything we wanted easily. Thank you. "
Wooded Restful Retreat, with broad scenic views, outdoor dining
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.