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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Our top choices for Healdsburg holiday homes

Love Shack private retreat
Property grounds

Love Shack private retreat

9.0 out of 10, Wonderful, (2)
"Natural light, high ceilings, ac, good WiFi and tv, great location, thoughtful host. "
The price is HK$719
HK$1,737 total
includes taxes & fees
25 Aug - 26 Aug
Love Shack private retreat
NEW Gurneville Backyard Oasis + Spa + Firepit + Dog Friendly + Wi-Fi
Private kitchen

NEW Gurneville Backyard Oasis + Spa + Firepit + Dog Friendly + Wi-Fi

10.0 out of 10, Exceptional, (1)
"The cabin is thoughtfully and beautifully appointed. Perfectly cozy for our group of three (two adults, one tween) and a dog. We really enjoyed our stay. Very close to a lot of fun activities and peaceful. Host Mike was awesome and communicative."
The price is HK$1,460
HK$3,470 total
includes taxes & fees
24 Aug - 25 Aug
NEW Gurneville Backyard Oasis + Spa + Firepit + Dog Friendly + Wi-Fi
Vineyard Oasis: Luxury Home in the Heart of Sonoma.
Fridge, microwave, oven, stovetop

Vineyard Oasis: Luxury Home in the Heart of Sonoma.

10.0 out of 10, Exceptional, (6)
"Great place in a beautiful setting. Looking forward to staying here again during the next trip."
The price is HK$1,555
HK$3,386 total
includes taxes & fees
10 Sept - 11 Sept
Vineyard Oasis: Luxury Home in the Heart of Sonoma.
Walk to Russian River - Casa Del Rio - Unit A
Interior

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 HK$859
HK$3,017 total
includes taxes & fees
17 Sept - 18 Sept
Walk to Russian River - Casa Del Rio - Unit A
Russian River Brew-cation Home
TV, fireplace

Russian River Brew-cation Home

10.0 out of 10, Exceptional, (51)
"3 couples had a great introduction to California wine country.!! Our stay here was the perfect โ€œbase campโ€ each days adventure. Would highly recommend staying here. "
Russian River Brew-cation Home
NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River
Exterior

NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River

The price is HK$1,734
HK$2,538 total
includes taxes & fees
25 Aug - 26 Aug
NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River
King Room ADA with Balcony
Living area

King Room ADA with Balcony

9.0 out of 10, Wonderful, (2)
"It was a nice room with a great view of the bay. The bed was vary comfortable. the hotel is under renovation and the grounds are in dire need of TLC. There is no sign for the hotel so watch for it also the spa was out of service but over all I would stay again"
The price is HK$1,456
HK$1,922 total
includes taxes & fees
7 Sept - 8 Sept
King Room ADA with Balcony
Winemaker's Delight: 3BD/3BA Russian River Valley
Outdoor dining

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

9.8 out of 10, Exceptional, (65)
"The house was in a great location, central to all the area attractions we were looking to visit. There was plenty of room to hang out and having 3 bathroom was a plus!"
The price is HK$2,149
HK$4,474 total
includes taxes & fees
7 Sept - 8 Sept
Winemaker's Delight: 3BD/3BA Russian River Valley
๐‘ณ๐’–๐’™๐’–๐’“๐’š ๐‘ท๐’“๐’Š๐’—๐’‚๐’•๐’† ๐‘ฌ๐’”๐’•๐’‚๐’•๐’† ๐’‚๐’• ๐’๐’๐’†๐’๐’๐’‚ ๐‘ฝ๐’Š๐’๐’†๐’š๐’‚๐’“๐’….๐‘ท๐‘ถ๐‘ถ๐‘ณ&๐‘บ๐‘ท๐‘จ!๐‘ฎ๐‘จ๐‘ด๐‘ฌ๐‘น๐‘ถ๐‘ถ๐‘ด!
Outdoor pool

๐‘ณ๐’–๐’™๐’–๐’“๐’š ๐‘ท๐’“๐’Š๐’—๐’‚๐’•๐’† ๐‘ฌ๐’”๐’•๐’‚๐’•๐’† ๐’‚๐’• ๐’๐’๐’†๐’๐’๐’‚ ๐‘ฝ๐’Š๐’๐’†๐’š๐’‚๐’“๐’….๐‘ท๐‘ถ๐‘ถ๐‘ณ&๐‘บ๐‘ท๐‘จ!๐‘ฎ๐‘จ๐‘ด๐‘ฌ๐‘น๐‘ถ๐‘ถ๐‘ด!

9.6 out of 10, Exceptional, (62)
"Great location next to some awesome wineries. Great place to relax after a day of wine tasting!"
The price is HK$11,214
HK$17,528 total
includes taxes & fees
25 Aug - 26 Aug
๐‘ณ๐’–๐’™๐’–๐’“๐’š ๐‘ท๐’“๐’Š๐’—๐’‚๐’•๐’† ๐‘ฌ๐’”๐’•๐’‚๐’•๐’† ๐’‚๐’• ๐’๐’๐’†๐’๐’๐’‚ ๐‘ฝ๐’Š๐’๐’†๐’š๐’‚๐’“๐’….๐‘ท๐‘ถ๐‘ถ๐‘ณ&๐‘บ๐‘ท๐‘จ!๐‘ฎ๐‘จ๐‘ด๐‘ฌ๐‘น๐‘ถ๐‘ถ๐‘ด!
AVL Private Retreat Cabin with hot tub on private wooded property
Living area

AVL Private Retreat Cabin with hot tub on private wooded property

The price is HK$2,031
HK$4,290 total
includes taxes & fees
29 Aug - 30 Aug
AVL Private Retreat Cabin with hot tub on private wooded property
Farpoint: Heated Infinity Pool, Mountain Views
A heated pool

Farpoint: Heated Infinity Pool, Mountain Views

9.8 out of 10, Exceptional, (7)
"Great location with lots of amenities. Very calming atmosphere. Very attentive staff. Canโ€™t wait to go back."
The price is HK$4,367
HK$8,141 total
includes taxes & fees
25 Aug - 26 Aug
Farpoint: Heated Infinity Pool, Mountain Views
Double Queen Room with Ocean View!
1 bedroom

Double Queen Room with Ocean View!

8.4 out of 10, Very good, (11)
"The rooms were clean and spacious and very affordably price! Upon checking in clear directions were given to get to and access the room. Overall environment was very quiet and made for an enjoyable stay."
The price is HK$1,482
HK$1,953 total
includes taxes & fees
2 Sept - 3 Sept
Double Queen Room with Ocean View!
Sonoma Wine Country Home: Pool, Hot Tub & Fun!
Terrace/patio

Sonoma Wine Country Home: Pool, Hot Tub & Fun!

10.0 out of 10, Exceptional, (8)
"We enjoyed the property very much"
The price is HK$6,189
HK$15,233 total
includes taxes & fees
16 Sept - 17 Sept
Sonoma Wine Country Home: Pool, Hot Tub & Fun!
Luxury Container Home w 360 Views + Infinity Pool
Outdoor pool, a heated pool

Luxury Container Home w 360 Views + Infinity Pool

10.0 out of 10, Exceptional, (10)
"This property was beautiful clean and comfortable. The beds were cozy and it was well stocked both kitchen and house supplies. We would definitely stay again!"
Luxury Container Home w 360 Views + Infinity Pool
Lovely Tudor Home w/ Pool & Spa Near Russian River
Property grounds

Lovely Tudor Home w/ Pool & Spa Near Russian River

2.0 star property
9.6 out of 10, Exceptional, (122)
"This house is such a great retreat for our friends every year. Plenty of space, and an ideal place to relax by the pool and BBQ on a warm weekend in Russian River."
The price is HK$5,812
HK$11,369 total
includes taxes & fees
28 Aug - 29 Aug
Lovely Tudor Home w/ Pool & Spa Near Russian River
Luxury Estate Awaits: Your Ultimate Vineyard Escape
Outdoor spa tub

Luxury Estate Awaits: Your Ultimate Vineyard Escape

The price is HK$5,415
HK$10,066 total
includes taxes & fees
11 Sept - 12 Sept
Luxury Estate Awaits: Your Ultimate Vineyard Escape
Cobb Mountain Chalet King Size Suite
Smart TV

Cobb Mountain Chalet King Size Suite

9.8 out of 10, Exceptional, (20)
"Perfect place to stay, nice and cozy!"
The price is HK$408
HK$1,134 total
includes taxes & fees
25 Aug - 26 Aug
Cobb Mountain Chalet King Size Suite
Garden house with gas fireplace
Outdoor dining

Garden house with gas fireplace

10.0 out of 10, Exceptional, (1)
"We were not originally planning on staying in Middletown but were pleasantly surprised on arrival. The Garden House is very comfortable and convenient to many things in town. Linda, our host had special little touches that made the stay relaxing. Number one the shower is amazing! I looked forward to it every evening the pressure and hot water is perfect and the quality shampoos and soaps provides smelled wonderful! The kitchen is well stocked if you are cooking during your stay. And there is...
The price is HK$719
HK$1,737 total
includes taxes & fees
25 Aug - 26 Aug
Garden house with gas fireplace
Glen Ellen Retreat #1 Hot Tub and King Beds
Fridge, microwave, oven, stovetop

Glen Ellen Retreat #1 Hot Tub and King Beds

10.0 out of 10, Exceptional, (66)
"Great place to relax. Nice backyard with hot tub. "
The price is HK$1,274
HK$3,186 total
includes taxes & fees
3 Sept - 4 Sept
Glen Ellen Retreat #1 Hot Tub and King Beds
Secret Garden: 1BR Oasis, Dog Friendly
Beach

Secret Garden: 1BR Oasis, Dog Friendly

9.6 out of 10, Exceptional, (5)
The price is HK$1,007
HK$3,159 total
includes taxes & fees
8 Sept - 9 Sept
Secret Garden: 1BR Oasis, Dog Friendly
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

The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton

10/10 Excellent
"Property had a very nice theme. The grounds were very well done with the wine country theme "
Robert 3-night trip
Posted 2 days ago
The Lodge at Healdsburg, Tapestry Collection by Hilton