Healdsburg Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Dec 12 - Dec 14
In two months
Jan 23 - Jan 25
In three months
Feb 20 - Feb 22
In four months
Mar 20 - Mar 22

Vacation Rentals in Healdsburg

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

Cottage in Forestville

10.0 out of 10, Exceptional, (11)
"Ideal for a relaxing time in wine country! The winery on property is fantastic and highly recommend it!"
United States
Paul H.
$446 nightly
The price is $501
Dec 1 - Dec 2
Total with taxes and fees
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Outdoor dining
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

Cabin in Guerneville

10.0 out of 10, Exceptional, (1)
"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.
$454 nightly
The price is $510
Nov 30 - Dec 1
Total with taxes and fees
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Interior
Walk to Russian River - Casa Del Rio - Unit A

Vacation Home in Forestville

9.2 out of 10, Wonderful, (38)
"Would definitely go back"
United States
liz n.
$377 nightly
The price is $390
Dec 2 - Dec 3
Total with taxes and fees
Walk to Russian River - Casa Del Rio - Unit A
Outdoor dining
Winemaker's Delight: 3BD/3BA Russian River Valley

Vacation Home in Northwest Santa Rosa

9.8 out of 10, Exceptional, (70)
"Comfortable beds and clean place. We enjoyed it"
United States
Amy F.
$426 nightly
The price is $467
Dec 2 - Dec 3
Total with taxes and fees
Winemaker's Delight: 3BD/3BA Russian River Valley
Fridge, microwave, oven, stovetop
Sonoma Getaway: Winemakerโ€™s Home with Modern Amenities

Vacation Home in Northwest Santa Rosa

10.0 out of 10, Exceptional, (77)
"Home was as advertised. Clean, equipped, lovely backyard. Great communication from host."
United States
carole e.
$427 nightly
The price is $468
Nov 30 - Dec 1
Total with taxes and fees
Sonoma Getaway: Winemakerโ€™s Home with Modern Amenities
Fridge, microwave, oven, stovetop
Creekside Under the Redwoods

Mobile Home in Guerneville

10.0 out of 10, Exceptional, (15)
"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 traveler
$307 nightly
The price is $340
Nov 30 - Dec 1
Total with taxes and fees
Creekside Under the Redwoods
TV, fireplace
Russian River Brew-cation Home

Vacation Home in Northwest Santa Rosa

10.0 out of 10, Exceptional, (54)
"My family of 6 adults enjoyed this lovely home. It was as advertised and there were even little extras like labels and notes to find things, a basket of necessities in case we forgot something, and everything you could think of to make us feel comfortable and at home. Thank-you!!"
United States
Sherrie R.
$432 nightly
The price is $474
Nov 30 - Dec 1
Total with taxes and fees
Russian River Brew-cation Home
Terrace/patio
Peaceful Redwood Hideaway - Hot Tub, Hammock, Walk to Russian River and Downtown

Cabin in Guerneville

10.0 out of 10, Exceptional, (43)
"Great location, clean and comfortable, will definitly come back.. "
United States
Marc S.
$433 nightly
The price is $479
Nov 30 - Dec 1
Total with taxes and fees
Peaceful Redwood Hideaway - Hot Tub, Hammock, Walk to Russian River and Downtown
Property grounds
Redwoods getaway w/ decks & fenced yard

Vacation Home in Guerneville

9.0 out of 10, Wonderful, (2)
"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.
$377 nightly
The price is $417
Dec 1 - Dec 2
Total with taxes and fees
Redwoods getaway w/ decks & fenced yard
Exterior
NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River

Apartment in Guerneville

9.0 out of 10, Wonderful, (4)
"This was a beautiful, quiet and lovely spot.It was very clean and comfortable and private."
United States
Cheryl P.
$293 nightly
The price is $324
Nov 30 - Dec 1
Total with taxes and fees
NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River
Exterior
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6

Condo in Windsor

9.2 out of 10, Wonderful, (43)
"Check-in was a little difficult, but the condo itself was convenient and a great stay."
United States
SB L.
$506 nightly
The price is $560
Nov 30 - Dec 1
Total with taxes and fees
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Outdoor spa tub
Heron House | A Wine Country Escape

Vacation Home in Healdsburg

10.0 out of 10, Exceptional, (26)
"Loved this house for a weekend getaway. We loved taking advantage of the deck, grill, and river access. Short drive to the town square and wineries."
United States
Maria D.
$895 nightly
The price is $1,005
Dec 27 - Dec 28
Total with taxes and fees
Heron House | A Wine Country Escape
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!

Vacation Home in Healdsburg

9.6 out of 10, Exceptional, (64)
"Great location next to some awesome wineries. Great place to relax after a day of wine tasting!"
United States
Michael Z.
$1,551 nightly
The price is $1,714
Dec 1 - Dec 2
Total with taxes and fees
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!
Pool
NEW! Adventure Alexander Valley Lodge with Pool & Hot tub

Villa in Geyserville

2.0 star property
$1,046 nightly
The price is $1,176
Dec 1 - Dec 2
Total with taxes and fees
NEW! Adventure Alexander Valley Lodge with Pool & Hot tub
A heated pool
Farpoint: Heated Infinity Pool, Mountain Views

Vacation Home in Santa Rosa

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."
United States
Christy
$852 nightly
The price is $942
Dec 11 - Dec 12
Total with taxes and fees
Farpoint: Heated Infinity Pool, Mountain Views
Fridge, microwave, oven, stovetop
Wineries & Wine: A Comforting Getaway in Wine Country

Vacation Home in Northwest Santa Rosa

9.4 out of 10, Exceptional, (22)
"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.
$372 nightly
The price is $408
Nov 29 - Nov 30
Total with taxes and fees
Wineries & Wine: A Comforting Getaway in Wine Country
Property grounds
Healdsburg Plaza Gem | A Wine Country Escape

Cottage in Healdsburg

9.8 out of 10, Exceptional, (44)
"Everything was excellent. The accommodations were clean and comfortable with everything we would want. The location was perfect, walking distance to everywhere. The communication with the property manager was fast and complete. I would totally recommend."
United States
Jean S.
$1,026 nightly
The price is $1,132
Nov 29 - Nov 30
Total with taxes and fees
Healdsburg Plaza Gem | A Wine Country Escape
Outdoor spa tub
Private Vineyard Estate | Sleeps 10

Vacation Home in Windsor

10.0 out of 10, Exceptional, (2)
"Stayed here for a wedding "
United States
Lanna E.
$935 nightly
The price is $1,033
Nov 30 - Dec 1
Total with taxes and fees
Private Vineyard Estate | Sleeps 10
Exterior
Enchanting Retreat in the heart of Redwoods

Mobile Home in Guerneville

8.8 out of 10, Excellent, (12)
"The property/rental itself is vety nice and well appointed. However, the location leaves a little to be desired. It's essentially a trailer park and not the "nestled in the redwoods" place we were thinking it would be. Property owner/manager was very responsive throughout the rental process."
United States
Tim L.
$307 nightly
The price is $340
Nov 30 - Dec 1
Total with taxes and fees
Enchanting Retreat in the heart of Redwoods
Interior
Tranquil Redwood Retreat

Mobile Home in Guerneville

8.8 out of 10, Excellent, (10)
"We had a lovely stay at the Tranquil Redwood Retreat! The cabin was clean, cozy, and beautifully decoratedโ€”just like the photos. The kitchen was fully stocked with everything we needed, and the check-in process was smooth and easy. It was the perfect spot for a peaceful getaway surrounded by nature. We made some great memories here and would definitely love to come back!"
United States
Stacie L.
$307 nightly
The price is $340
Nov 30 - Dec 1
Total with taxes and fees
Tranquil Redwood Retreat
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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Healdsburg Hotel Reviews

The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton

10/10 Excellent
"Spacious, well-appointed and very clean rooms. Loved the fireplace."
Suzanne 1-night trip
Posted 18 hours ago
The Lodge at Healdsburg, Tapestry Collection by Hilton

Find out more about Healdsburg

Everything you need to know about Healdsburg vacation rentals

Whether youโ€™re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, weโ€™ve got the Healdsburg vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on โ€ฆand on.

Thereโ€™s just as wide a choice of amenities, too. Maybe youโ€™re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Healdsburg vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Healdsburg vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Healdsburg. If youโ€™re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Healdsburg in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $68 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Healdsburg rentals

At Expedia, we put the best Healdsburg vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. Youโ€™ll always find a great deal with Expedia.

To find some top Healdsburg rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you wantโ€”and just like that, youโ€™ve built your dream Healdsburg vacation.

If youโ€™re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Healdsburg. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH: This vacation home rental outside of Healdsburg is located by the ocean and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

How many vacation rentals are there in Healdsburg?

Expedia has 137 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 Jordan Vineyard & 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.