Healdsburg Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Healdsburg vacation rentals

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)
"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 ￥15,630
￥50,979 total
includes taxes & fees
Feb 18 - Feb 19
Wineries & Wine: A Comforting Getaway in Wine Country
Dining

Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (13 reviews)
"Love the cabin atmosphere, big windows overlooking the trees and river. It’s my happy place. Been there twice and already planning my next stay."
United States
Sydney G.
The price is ￥20,859
￥74,922 total
includes taxes & fees
Feb 19 - Feb 20
Cozy Riverfront Cabin - Beach Access & Wood Stove
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 ￥21,515
￥47,022 total
includes taxes & fees
Feb 17 - Feb 18
Enchanting Retreat in the heart of Redwoods
Smart TV, DVD player, books, video library

River Retreat - Hot Tub and Tastings Included

River Retreat - Hot Tub and Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (2 reviews)
"The house is in a great secluded location just outside of Healdsburg. It is very easy to get to town, and the house itself is well stocked. We really enjoyed our stay!"
United States
James B.
River Retreat - Hot Tub and Tastings Included
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 ￥22,558
￥68,778 total
includes taxes & fees
Feb 16 - Feb 17
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Property grounds

Redwoods getaway w/ decks & fenced yard

Redwoods getaway w/ decks & fenced yard
Guerneville
9.0 out of 10, Wonderful, (2 reviews)
"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."
United States
Beth G.
The price is ￥24,144
￥68,676 total
includes taxes & fees
Feb 16 - Feb 17
Redwoods getaway w/ decks & fenced yard
Interior

Private Vineyard-View Wine Country Home Near Healdsburg

Private Vineyard-View Wine Country Home 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 ￥30,747
￥65,135 total
includes taxes & fees
Feb 17 - Feb 18
Private Vineyard-View Wine Country Home 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 ￥31,721
￥109,431 total
includes taxes & fees
Mar 11 - Mar 12
Secluded Home, Wine Tastings Included
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 ￥34,019
￥49,778 total
includes taxes & fees
Feb 13 - Feb 14
NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River
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 ￥30,801
￥67,579 total
includes taxes & fees
Feb 18 - Feb 19
Sonoma Getaway: Winemaker’s Home with Modern Amenities
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 ￥30,648
￥57,140 total
includes taxes & fees
Feb 16 - Feb 17
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
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 ￥33,866
￥80,794 total
includes taxes & fees
Feb 17 - Feb 18
Russian River Brew-cation Home
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, (45 reviews)
"Great location, very clean, private hot tub, bed was comfortable. "
United States
Peter J.
The price is ￥37,544
￥73,586 total
includes taxes & fees
Feb 17 - Feb 18
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)
"Comfortable beds and clean place. We enjoyed it"
United States
Amy F.
The price is ￥38,004
￥84,071 total
includes taxes & fees
Feb 22 - Feb 23
Winemaker's Delight: 3BD/3BA Russian River Valley
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)
"The entry was simple as was the exit. The kitchen wasvwell appointed. We were a party of three and the layout worked well. We appreciated how quiet it was."
United States
Flavia G.
The price is ￥35,360
￥114,783 total
includes taxes & fees
Mar 1 - Mar 2
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 ￥30,188
￥84,922 total
includes taxes & fees
Feb 17 - Feb 18
Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
Dining

Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is ￥20,687
￥50,630 total
includes taxes & fees
Feb 18 - Feb 19
Wine Country Cottage Escape
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 ￥58,614
￥129,610 total
includes taxes & fees
Feb 16 - Feb 17
Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar
Dining

Elegant Vineyard Living at a Private Wine Country Estate

Elegant Vineyard Living at a Private Wine Country Estate
Windsor
8.4 out of 10, Very Good, (6 reviews)
"Stayed here for a wedding "
United States
Lanna E.
The price is ￥51,029
￥132,648 total
includes taxes & fees
Feb 18 - Feb 19
Elegant Vineyard Living at a Private Wine Country Estate
Exterior

Healdsburg Plaza Charmer w/ Hot Tub & Fire Pit

Healdsburg Plaza Charmer w/ Hot Tub & Fire Pit
Healdsburg
10.0 out of 10, Exceptional, (15 reviews)
"great location! the cottage was perfect for our trip with pets."
United States
Sue P.
The price is ￥52,293
￥108,871 total
includes taxes & fees
Mar 2 - Mar 3
Healdsburg Plaza Charmer w/ Hot Tub & Fire Pit
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

Fairview Inn and Suites

Fairview Inn and Suites

10/10 Excellent
"Staff helpful, even when we arrived really late due to a delayed flight. "
Marianne 1-night trip
Posted 2 days ago
Fairview Inn and Suites

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:

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

Frequently asked questions

Are there vacation rentals in Healdsburg?

Yes, there are vacation rentals in Healdsburg near SingleThread Farm at Dry Creek, or you can choose a secluded option if you want 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's the top vacation rental that Healdsburg has to offer?

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

How many vacation rentals are there in Healdsburg?

Expedia has 143 vacation 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 vacation rentals like in Healdsburg?

Vacation rentals are privately owned properties you can book for several days or more in Healdsburg. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for small groups.