Healdsburg Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

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

Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.6 out of 10, Exceptional, (15 reviews)
"Wonderful location and had everything we needed! "
United States
Maryrose H.
The price is HK$1,056
HK$3,817 total
includes taxes & fees
2 Mar - 3 Mar
Cozy Riverfront Cabin - Beach Access & Wood Stove
Terrace/patio

Peaceful Redwood Hideaway - Hot Tub, Hammock, Walk to Russian River and Downtown

Peaceful Redwood Hideaway - Hot Tub, Hammock, Walk to Russian River and Downtown
Guerneville
10.0 out of 10, Exceptional, (46 reviews)
"Great location, very clean, private hot tub, bed was comfortable. "
United States
Peter J.
Peaceful Redwood Hideaway - Hot Tub, Hammock, Walk to Russian River and Downtown
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)
"The absolutely perfect home and location! We enjoyed the Graton Casino, shopping and wineries! The photos were on-point for the comfort, beauty and spaciousness of this home. We truly appreciated the amenities, fully-stocked home and especially the en-suite accommodations for every room. It was the perfect getaway for me and my family. Thank you! "
United States
Monica M.
The price is HK$1,917
HK$4,297 total
includes taxes & fees
2 Mar - 3 Mar
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$1,098
HK$2,393 total
includes taxes & fees
2 Mar - 3 Mar
Enchanting Retreat in the heart of Redwoods
TV, fireplace

Tranquil Redwood Retreat

Tranquil Redwood Retreat
Guerneville
8.8 out of 10, Excellent, (10 reviews)
"Perfect hun for enjoying downtown guernville "
United States
Alex A.
The price is HK$1,183
HK$2,503 total
includes taxes & fees
2 Mar - 3 Mar
Tranquil Redwood Retreat
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$1,737
HK$2,541 total
includes taxes & fees
2 Mar - 3 Mar
NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River

Vineyard-View Wine Country Retreat Near Healdsburg

Vineyard-View Wine Country Retreat Near Healdsburg
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$1,612
HK$3,368 total
includes taxes & fees
15 Mar - 16 Mar
Vineyard-View Wine Country Retreat Near Healdsburg
Exterior

Secluded Home, Wine Tastings Included

Secluded Home, Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (2 reviews)
"Was a great stay. Very much appreciated the location, amenities and communication."
United States
Jill M.
The price is HK$1,619
HK$5,587 total
includes taxes & fees
11 Mar - 12 Mar
Secluded Home, Wine Tastings Included
Property grounds

Redwoods getaway w/ decks & fenced yard

Redwoods getaway w/ decks & fenced yard
Guerneville
9.0 out of 10, Wonderful, (2 reviews)
"Nice kitchen, comfortable bed, and clean spa. Easy entry with plenty of parking. "
United States
Scott L.
Redwoods getaway w/ decks & fenced yard
Dining

Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is HK$1,291
HK$2,899 total
includes taxes & fees
3 Mar - 4 Mar
Wine Country Cottage Escape
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$1,572
HK$3,481 total
includes taxes & fees
2 Mar - 3 Mar
Sonoma Getaway: Winemaker’s Home with Modern Amenities
Terrace/patio

Vista Retreat with Hot Tub and Tastings Included

Vista Retreat with Hot Tub and Tastings Included
Guerneville
10.0 out of 10, Exceptional, (86 reviews)
"Fully stocked kitchen was amazing for making meals. House was very clean and in a quiet neighborhood. "
United States
Joey W.
Vista Retreat with Hot Tub and Tastings Included
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$1,541
HK$4,336 total
includes taxes & fees
2 Mar - 3 Mar
Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
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, (23 reviews)
"enjoyed our stay, no surprises and a good value"
United States
Craig M.
The price is HK$1,220
HK$3,162 total
includes taxes & fees
14 Mar - 15 Mar
Wineries & Wine: A Comforting Getaway in Wine Country
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$1,909
HK$4,353 total
includes taxes & fees
15 Mar - 16 Mar
Russian River Brew-cation Home
Smart TV, stereo

❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤

❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤
Healdsburg
10.0 out of 10, Exceptional, (4 reviews)
"This property was amazing! I will definitely stay here again."
United States
Shauntele J.
The price is HK$782
HK$2,577 total
includes taxes & fees
2 Mar - 3 Mar
❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤
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, (44 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$1,565
HK$2,917 total
includes taxes & fees
2 Mar - 3 Mar
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Interior

Botany House Designer Home with Hot Tub

Botany House Designer Home with Hot Tub
Northwest Santa Rosa
10.0 out of 10, Exceptional, (11 reviews)
"Great stay"
United States
Gabriela L.
The price is HK$1,740
HK$4,900 total
includes taxes & fees
24 Mar - 25 Mar
Botany House Designer Home with Hot Tub
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
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$3,697
HK$7,492 total
includes taxes & fees
2 Mar - 3 Mar
Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar
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

Hotel Trio Healdsburg

Hotel Trio Healdsburg

10/10 Excellent
"Super clean, organized and fantastic staff."
Tim 4-night trip
Posted 3 days ago
Hotel Trio Healdsburg

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?

Bodega Bay on the Edge of Pacific Ocean: This holiday home rental outside of Healdsburg is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in Healdsburg?

Expedia has 138 holiday rentals for your stay in Healdsburg.

What can I see and do in Healdsburg?

Russian River and Healdsburg Ridge Open Space Preserve are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include SingleThread Farm at Dry Creek. Healdsburg Plaza and Jordan Vineyard & 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.