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Healdsburg Holiday Rentals

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Check prices for these dates

Tonight
15 Jan - 16 Jan
Tomorrow
16 Jan - 17 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

Our top choices for Healdsburg holiday rentals

Outdoor dining

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Guerneville
10.0 out of 10, Exceptional, (1 review)
"Our stay was fantastic! The cabin was everything we needed for a few days; cozy, and quiet. The outdoor spaces were great and the hot tub was perfect at the end of the day. The host was super helpful and responded to my questions almost immediately. "
United States
Rosa N.
The price is HK$1,193
HK$3,766 total
includes taxes & fees
19 Jan - 20 Jan
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Outdoor dining

True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard

True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Forestville
10.0 out of 10, Exceptional, (11 reviews)
"Ideal for a relaxing time in wine country! The winery on property is fantastic and highly recommend it!"
United States
Paul H.
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Dining

Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (13 reviews)
"Wonderful location and had everything we needed! "
United States
Maryrose H.
The price is HK$1,107
HK$3,906 total
includes taxes & fees
19 Jan - 20 Jan
Cozy Riverfront Cabin - Beach Access & Wood Stove
Fridge, microwave, oven, stovetop

Wineries & Wine: A Comforting Getaway in Wine Country

Wineries & Wine: A Comforting Getaway in Wine Country
Northwest Santa Rosa
9.4 out of 10, Exceptional, (22 reviews)
"This is a great location, and comfortable space for us to tour wine country! We enjoyed the condo, it was quite and clean."
United States
Gayle C.
The price is HK$858
HK$2,673 total
includes taxes & fees
19 Jan - 20 Jan
Wineries & Wine: A Comforting Getaway in Wine Country
TV, fireplace

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

Winemaker's Delight: 3BD/3BA Russian River Valley
Northwest Santa Rosa
9.8 out of 10, Exceptional, (72 reviews)
"Comfortable beds and clean place. We enjoyed it"
United States
Amy F.
The price is HK$1,310
HK$3,520 total
includes taxes & fees
9 Feb - 10 Feb
Winemaker's Delight: 3BD/3BA Russian River Valley
Exterior

Enchanting Retreat in the heart of Redwoods

Enchanting Retreat in the heart of Redwoods
Guerneville
8.8 out of 10, Excellent, (12 reviews)
"Beautiful, clean house nestled in the woods. Loved the hot tub and the fire pit in the AM. Super comfortable mattresses."
United States
Jennifer H.
The price is HK$1,179
HK$2,518 total
includes taxes & fees
19 Jan - 20 Jan
Enchanting Retreat in the heart of Redwoods
Outdoor pool, a heated pool

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

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Healdsburg
10.0 out of 10, Exceptional, (66 reviews)
"This place was beautiful and we had such a lovely stay. Would recommend and also stay here again! Hosts were communicative and Andy at the property’s winery (Limerick) was an absolute gem! 🥹"
United States
Alex D.
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Interior

Private Vineyard-View Wine Country Home Near Healdsburg and Sonoma Wineries

Private Vineyard-View Wine Country Home Near Healdsburg and Sonoma Wineries
Healdsburg
10.0 out of 10, Exceptional, (8 reviews)
"Kitchen was great, easy area for our dog.."
United States
Brad G.
The price is HK$1,552
HK$3,287 total
includes taxes & fees
20 Jan - 21 Jan
Private Vineyard-View Wine Country Home Near Healdsburg and Sonoma Wineries
Exterior

Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa

Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa
3.5 star property
Geyserville
The price is HK$3,747
HK$9,146 total
includes taxes & fees
20 Jan - 21 Jan
Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa
Dining

Sonoma Getaway: Winemaker’s Home with Modern Amenities

Sonoma Getaway: Winemaker’s Home with Modern Amenities
Northwest Santa Rosa
10.0 out of 10, Exceptional, (78 reviews)
"The house was very clean and cozy in a cute neighborhood. Very nice backyard space and interior, would definitely recommend and stay again."
United States
Gary R.
The price is HK$1,505
HK$3,810 total
includes taxes & fees
24 Jan - 25 Jan
Sonoma Getaway: Winemaker’s Home with Modern Amenities
Dining

Russian River Brew-cation Home

Russian River Brew-cation Home
Northwest Santa Rosa
10.0 out of 10, Exceptional, (55 reviews)
"The house was great! We enjoyed our stay"
United States
Warren M.
The price is HK$1,482
HK$3,804 total
includes taxes & fees
19 Jan - 20 Jan
Russian River Brew-cation Home
TV, fireplace, books, offices

Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C

Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
Forestville
The price is HK$1,622
HK$4,563 total
includes taxes & fees
19 Jan - 20 Jan
Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
A heated pool

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Windsor
9.2 out of 10, Wonderful, (43 reviews)
"Check-in was a little difficult, but the condo itself was convenient and a great stay."
United States
SB L.
The price is HK$1,560
HK$2,931 total
includes taxes & fees
19 Jan - 20 Jan
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Property grounds

Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar

Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar
2.5 star property
Geyserville
9.2 out of 10, Wonderful, (15 reviews)
"Fabulous property perfect for our needs. Family was able to stay together eat meals together in the big kitchen enjoy fantastic outdoor time together - really nice ambience and breathtaking views."
United States
Margo R.
The price is HK$4,842
HK$8,928 total
includes taxes & fees
26 Jan - 27 Jan
Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar
Property grounds

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

NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River
Guerneville
9.0 out of 10, Wonderful, (4 reviews)
"This was a beautiful, quiet and lovely spot.It was very clean and comfortable and private."
United States
Cheryl P.
The price is HK$1,731
HK$2,525 total
includes taxes & fees
16 Jan - 17 Jan
NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River
Exterior detail

Luxury Private Estate at Zoella Vineyards in the heart of Wine Country

Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
Healdsburg
9.6 out of 10, Exceptional, (65 reviews)
"Better than expected!! We loved this properly and would most definitely stay again!! It was perfect and magical in every way!!! "
United States
Elaine G.
The price is HK$11,193
HK$17,449 total
includes taxes & fees
19 Jan - 20 Jan
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
Pool

NEW! Adventure Alexander Valley Lodge with Pool & Hot tub

NEW! Adventure Alexander Valley Lodge with Pool & Hot tub
2.0 star property
Geyserville
The price is HK$4,260
HK$9,506 total
includes taxes & fees
20 Jan - 21 Jan
NEW! Adventure Alexander Valley Lodge with Pool & Hot tub
A heated pool

Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views
Santa Rosa
9.8 out of 10, Exceptional, (9 reviews)
"Great location with lots of amenities. Very calming atmosphere. Very attentive staff. Can’t wait to go back."
United States
Christy
The price is HK$3,158
HK$6,687 total
includes taxes & fees
21 Jan - 22 Jan
Farpoint: Heated Infinity Pool, Mountain Views
Exterior

Luxury Hilltop Villa | Pool, Hot Tub & Close to Downtown

Luxury Hilltop Villa | Pool, Hot Tub & Close to Downtown
Healdsburg
The price is HK$6,909
HK$13,636 total
includes taxes & fees
20 Jan - 21 Jan
Luxury Hilltop Villa | Pool, Hot Tub & Close to Downtown
Interior

Creekside Under the Redwoods

Creekside Under the Redwoods
Guerneville
9.8 out of 10, Exceptional, (17 reviews)
"Very enjoyable stay at this place. Very cute and charming and had everything we needed. Close to restaurants and shopping. I'd definitely stay here again."
United States
Anonymous traveller
The price is HK$1,179
HK$2,495 total
includes taxes & fees
2 Feb - 3 Feb
Creekside Under the Redwoods
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

Best Western Dry Creek Inn

Best Western Dry Creek Inn

10/10 Excellent
"Clean room, comfortable bed and exactly what we needed for our weekend in town. "
Ariana 2-night trip
Posted 1 day ago
Best Western Dry Creek Inn

Find out more about Healdsburg

Search for holiday rentals in Healdsburg on Expedia! You can easily find your home rentals, villas, holiday apartments in Healdsburg using one of the methods below:

  • View our selection of featured holiday rentals in Healdsburg
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  • Enter your travel dates to view the best deals on holiday rentals in Healdsburg while they last

Look no further and take a look at our great range of rental properties in Healdsburg!

Frequently asked questions

Are there holiday rentals in Healdsburg?

Yes, there are holiday rentals in Healdsburg close to SingleThread Farm at Dry Creek, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the array of shops and scenic riverfront in Healdsburg. While you're here, grab a bite or have a drink at the wineries and top-notch restaurants.

What are some of the best holiday rentals that Healdsburg has to offer?

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg: This highly rated holiday home rental in Healdsburg is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Healdsburg?

Expedia has 141 holiday rentals for your stay in Healdsburg.

What can I see and do in Healdsburg?

Enjoy the outdoors at Russian River and Healdsburg Ridge Open Space Preserve, or simply take in cultural attractions like Healdsburg Museum and Raven Performing Arts Theater. Healdsburg Plaza and Wilson Winery are other places to visit while you're in town.

What are holiday rentals like in Healdsburg?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Healdsburg. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family trip or a small group gathering.