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Compare 238 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, (26)
"The family and I had a fun stay at Casa Del Rio. Couple of things to make note of: 1) the unit is on the third floor. Access is via a super-sturdy staircase on the river side of the building. You have to carry everything up. 2) there is a neighbor dog that starts barking around 5am and barks every few minutes until 8am. I believe the dog barking and the run down property to the east are a package. 3) the unit is clean and everything is functional. The floors aren't all plumb so pay attention to...
The price is SAR 383
SAR 1,340 total
includes taxes & fees
6 Apr - 7 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, (122)
"The property was well maintained and very nice for a group of eight or so. (We had six.) We were there in the off season (February) so didn't get to enjoy the outdoor space as much as I think we would in warmer weather. "
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, (69)
"I picked this property to have a couple of friends come out to help celebrate a milestone birthday. We had a great time at the house which is set up perfectly. The common area has a ton of space and is good for when everyone wants to be together and good if people want a little separation. All of the bedrooms are in separate corners of the house which is also nice. Would love to come back in the warmer months when we can use the dock. Great location for a quick walk into town for coffee and for...
~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

9.8 out of 10, Exceptional, (10)
"This was the perfect location and a beautiful space for our family reunion. The sweetest touch was a high chair for my neice, along with bathroom amenities.Highly recommend!! "
The Sonoma Valley Cottage

Wine Country Get Away

10.0 out of 10, Exceptional, (25)
"Overall stay was good and the location is great for visits to Wine Country. Host was accessible and helpful. "
The price is SAR 634
SAR 1,656 total
includes taxes & fees
7 Apr - 8 Apr
Wine Country Get Away

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

9.8 out of 10, Exceptional, (23)
"The house is exactly as described! It has everything you need whether you plan to take advantage of the amenities of the property or touring the surrounding wine country, or alittle of both. Joe was a great host, available and responsive to a few questions that we had. The house has a keurig and basic spices like salt/pepper and brita water jugs in the fridge. I would stay here again for sure next time I am in Sonoma. "
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, (22)
"We met up with our out of town family for the holidays at Reflections and it was perfect for us. It was very clean, the beds were comfortable, the hot tub was nice, and we really liked having the separate spaces which gave everyone plenty of room. We’d love to visit again when it is warm enough to use the pool."
~ 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

9.4 out of 10, Exceptional, (10)
"Place was clean and comfortable. Easy check in. Provided with access code that is a full 10-digit phone number...so not easy to memorize and had to bring code with when leaving the home. Good location in terms of closeness to town for easy walking. Loud in terms of being located on road just behind the main highway. Weird in terms of the back dirt road seems to be used as a dump for random housing appliances and garbage halfway between home and traffic light. Comfortable inside, bedding and...
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."
The price is SAR 1,853
SAR 3,694 total
includes taxes & fees
1 Apr - 2 Apr
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!"
The price is SAR 548
SAR 1,539 total
includes taxes & fees
28 Apr - 29 Apr
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, (2)
"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, (57)
"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 SAR 4,059
SAR 6,710 total
includes taxes & fees
1 Apr - 2 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, (165)
" Place is a real gem: Beautiful views of the Russian River valley from the house and from several decks; Spacious and comfortable inside; Hot tub outside on deck with beautiful view of the valley; easy walk to water. We also did some nearby hikes and spent time in the lovely town of Healdsburg. Owner Stephen and manager Tenay were great hosts."
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, (54)
"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, (283)
"My spouse and I celebrated our 44th anniversary with a second stay at the cabin in Rogers Vineyard. The cabin is on a hill surrounded by beautiful vineyards and views of the mountains. It is a peaceful refuge. Everything you could possibly need was provided, including beautiful fresh flowers, an overflowing library, a selection of beverages, and a full kitchen with all essentials. We enjoyed meals that we prepared and also those from a few excellent Healdsburg restaurants. We visited the Due...
✨Rustic Cabin in Dry Creek Valley with beautiful views // 5 miles to Plaza ✨

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

10.0 out of 10, Exceptional, (144)
"Beautiful setting with a wonderful home. Loved the location near Healdsburg. Everything was convenient. The property manager was fantastic!"
Renovated Vineyard Home - 4 BR/4 BA - Solar Pool, Spa, Views

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

10.0 out of 10, Exceptional, (240)
"We so enjoyed our stay! The location was lovely with amazing views, well stocked kitchen, super quiet and close to many wine tasting options. This is a well cared for family home and it feels like you are a guest of your own family member, not a generic VRBO property. Highly recommend!"
Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
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.