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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Compare 247 Vacation Homes in Healdsburg with updated reviews, rates, and availability.

Walk to Russian River - Casa Del Rio - Unit A
Fridge, microwave, oven, stovetop

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 AED 411
AED 1,339 total
includes taxes & fees
27 Apr - 28 Apr
Walk to Russian River - Casa Del Rio - Unit A
Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views
Outdoor spa tub

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

8.4 out of 10, Very Good, (23)
"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
Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country
Outdoor spa tub

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~
Outdoor spa tub

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

10.0 out of 10, Exceptional, (73)
"This home was ideal to celebrate my daughter's birthday with her friends! We enjoyed the location, and cooking up a feast. The dock was off limits because of the seasonal rains, however this news was communicated to us ahead of time and we made adjustments as to where to access the river and it did not impact our enjoyment for a long weekend. The girls loved the hot tubbing under the stars. Thank you for having us!"
~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
A heated pool

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
Wine Country Get Away
Exterior

Wine Country Get Away

9.8 out of 10, Exceptional, (27)
"Right next to trails and clean and quiet home with responsive host "
The price is AED 621
AED 1,394 total
includes taxes & fees
29 Apr - 30 Apr
Wine Country Get Away
5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley
Outdoor pool, a heated pool

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

9.8 out of 10, Exceptional, (26)
"Joe’s home was perfect for me and my group of friends. The home was warm and welcoming, decorated beautifully, and spacious. Joe was extremely responsive and a fabulous host. Would definitely stay again and recommend to anyone!"
5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley
~ Main House + 3 Private Guest Cottages ~ Hot Tub ~ Pool ~ Pet Friendly ~
Outdoor pool, a heated pool

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

9.8 out of 10, Exceptional, (25)
"This property was perfect for our family holiday. Everyone had their own space for naptimes ect and we were all able to hang out in the beautiful outdoor space. A overall wonderful experience and a beautiful property "
~ Main House + 3 Private Guest Cottages ~ Hot Tub ~ Pool ~ Pet Friendly ~
Luxurious Large Home, Beautiful Pool, Extensive Gardens
Outdoor pool, a heated pool

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
Property grounds

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
A heated pool

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
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (54)
"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 AED 896
AED 1,973 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
Terrace/patio

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!
Outdoor pool

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

9.6 out of 10, Exceptional, (60)
"Great location next to some awesome wineries. Great place to relax after a day of wine tasting!"
The price is AED 3,427
AED 5,939 total
includes taxes & fees
27 Apr - 28 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!
Golf

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
Exterior

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
Game room

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
Property grounds

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!
A heated pool

Private Vineyard Haven--walk to the HBG Square!

9.8 out of 10, Exceptional, (56)
"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!
Riverfront, dog-friendly home with private hot tub, fireplaces & amazing decks
Fridge, microwave, oven, stovetop

Riverfront, dog-friendly home with private hot tub, fireplaces & amazing decks

8.0 out of 10, Very Good, (13)
"This large river home is full of character and has everything you need in kitchen and laundry room. Location is wonderful, beautiful yard, private beach and canoe. Only complaints are the spa was out of order and it was a big reason we picked this property. Also the pull out sofa which is included as a bed for 2 was very old and had thin mattress so no one slept on it. Luckily we brought an air mattress. The bathroom upstairs only has a tub, toilet and sink, no shower. "
Riverfront, dog-friendly home with private hot tub, fireplaces & amazing decks
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 ✨
Fridge, microwave, oven, stovetop

✨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 ✨
Wooded Restful Retreat, with broad scenic views, outdoor dining
Fridge, microwave, oven, stovetop

Wooded Restful Retreat, with broad scenic views, outdoor dining

10.0 out of 10, Exceptional, (301)
"We had a wonderful time introducing our neighbors to the area and this home was perfect! We relocated to Arizona 5 years ago and miss wine country so it was a perfect location to do some wine tasting in Alexander Valley, Napa, and Russian River areas. The home was very comfortable and quiet. Beds were comfy, kitchen was fully equipped, tv's in the bedrooms were a plus, and the main tv was easy to navigate. Highly recommend staying here!!"
Wooded Restful Retreat, with broad scenic views, outdoor dining
Renovated Vineyard Home - 4 BR/4 BA - Solar Pool, Spa, Views
Fridge, microwave, oven, stovetop

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
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.