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

Tonight
Oct 27 - Oct 28
Tomorrow
Oct 28 - Oct 29
This weekend
Oct 31 - Nov 2
Next weekend
Nov 7 - Nov 9

Vacation Rentals in Healdsburg

Fridge, microwave, oven, stovetop
Vineyard Oasis: Luxury Home in the Heart of Sonoma.
Vineyard Oasis: Luxury Home in the Heart of Sonoma.
10.0 out of 10, Exceptional, (7)
"We had a great time!The house was perfect for our needs!"
United States
Theresa C.
$363 nightly
The price is $401
Nov 10 - Nov 11
Total with taxes and fees
Vineyard Oasis: Luxury Home in the Heart of Sonoma.
Outdoor dining
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
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.
$492 nightly
The price is $553
Oct 29 - Oct 30
Total with taxes and fees
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
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.
$440 nightly
The price is $495
Nov 17 - Nov 18
Total with taxes and fees
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Outdoor dining
Riverside love shack
Riverside love shack
2.0 star property
$392 nightly
The price is $433
Oct 28 - Oct 29
Total with taxes and fees
Riverside love shack
Dining
Cozy Riverfront Cabin - Beach Access & Wood Stove
Cozy Riverfront Cabin - Beach Access & Wood Stove
9.6 out of 10, Exceptional, (10)
"Wonderful location and had everything we needed! "
United States
Maryrose H.
$418 nightly
The price is $470
Oct 30 - Oct 31
Total with taxes and fees
Cozy Riverfront Cabin - Beach Access & Wood Stove
Outdoor dining
Redwoods getaway w/ decks & fenced yard
Redwoods getaway w/ decks & fenced yard
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."
United States
Beth G.
$349 nightly
The price is $349
Oct 28 - Oct 29
Total with taxes and fees
Redwoods getaway w/ decks & fenced yard
Interior
Walk to Russian River - Casa Del Rio - Unit A
Walk to Russian River - Casa Del Rio - Unit A
9.2 out of 10, Wonderful, (37)
"Bright and cheerful home, 1 minute walk to the river. Our family had such a great trip. Thanks!"
United States
Sarah S.
$375 nightly
The price is $388
Oct 28 - Oct 29
Total with taxes and fees
Walk to Russian River - Casa Del Rio - Unit A
Outdoor dining
Winemaker's Delight: 3BD/3BA Russian River Valley
Winemaker's Delight: 3BD/3BA Russian River Valley
9.8 out of 10, Exceptional, (70)
"Lovely home! Will absolutely stay again "
United States
Kendra C.
$452 nightly
The price is $496
Oct 28 - Oct 29
Total with taxes and fees
Winemaker's Delight: 3BD/3BA Russian River Valley
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!
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, (64)
"Great location next to some awesome wineries. Great place to relax after a day of wine tasting!"
United States
Michael Z.
$1,963 nightly
The price is $2,177
Oct 28 - Oct 29
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!
Fridge, microwave, oven, stovetop
Creekside Under the Redwoods
Creekside Under the Redwoods
10.0 out of 10, Exceptional, (13)
"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
$311 nightly
The price is $344
Oct 28 - Oct 29
Total with taxes and fees
Creekside Under the Redwoods
Exterior
Puccioni Paradise | A Wine Country Escape
Puccioni Paradise | A Wine Country Escape
10.0 out of 10, Exceptional, (2)
"Was a great stay. Very much appreciated the location, amenities and communication."
United States
Jill M.
$623 nightly
The price is $700
Nov 5 - Nov 6
Total with taxes and fees
Puccioni Paradise | A Wine Country Escape
A heated pool
Sanctuary on Lytton | A Wine Country Escape
Sanctuary on Lytton | A Wine Country Escape
10.0 out of 10, Exceptional, (33)
"Such a fun property to stay at for an extended weekend! Great location and the hosts were easy to communicate with! "
United States
Allison H.
$2,069 nightly
The price is $2,333
Nov 19 - Nov 20
Total with taxes and fees
Sanctuary on Lytton | A Wine Country Escape
Property grounds
Rivers Breeze | A Wine Country Escape
Rivers Breeze | A Wine Country Escape
10.0 out of 10, Exceptional, (17)
"In Healdsburg to visit family and could not have had a more comfortable and lovely place to stay! It was impeccably clean, well located and so cute! We loved it!"
United States
Heather S.
$690 nightly
The price is $775
Nov 24 - Nov 25
Total with taxes and fees
Rivers Breeze | A Wine Country Escape
Exterior detail
NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River
NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River
9.4 out of 10, Exceptional, (3)
"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
Oct 28 - Oct 29
Total with taxes and fees
NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River
Outdoor spa tub
Luxury Estate Awaits: Your Ultimate Vineyard Escape
Luxury Estate Awaits: Your Ultimate Vineyard Escape
10.0 out of 10, Exceptional, (2)
"Stayed here for a wedding "
United States
Lanna E.
$1,091 nightly
The price is $1,206
Nov 3 - Nov 4
Total with taxes and fees
Luxury Estate Awaits: Your Ultimate Vineyard Escape
Exterior
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
9.0 out of 10, Wonderful, (12)
"Family members, 4 from ohio, 6 from san francisco. Pool and pool table provided hours of fun. Local wineries awesome dor thae adulats. Tons of space for 10 people. We liked it a lot!"
United States
Kelly H.
$846 nightly
The price is $934
Nov 10 - Nov 11
Total with taxes and fees
Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar
Property grounds
Healdsburg Plaza Gem | A Wine Country Escape
Healdsburg Plaza Gem | A Wine Country Escape
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.
$824 nightly
The price is $902
Oct 30 - Oct 31
Total with taxes and fees
Healdsburg Plaza Gem | A Wine Country Escape
Exterior
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
9.2 out of 10, Wonderful, (43)
"Very well maintained"
United States
Jim M.
$507 nightly
The price is $561
Nov 6 - Nov 7
Total with taxes and fees
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
A heated pool
Farpoint: Heated Infinity Pool, Mountain Views
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."
United States
Christy
$821 nightly
The price is $909
Oct 28 - Oct 29
Total with taxes and fees
Farpoint: Heated Infinity Pool, Mountain Views
Exterior
Enchanting Retreat in the heart of Redwoods
Enchanting Retreat in the heart of Redwoods
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.
$311 nightly
The price is $344
Oct 28 - Oct 29
Total with taxes and fees
Enchanting Retreat in the heart of 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.
View all properties
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

Hotel Trio Healdsburg

Hotel Trio Healdsburg

10/10 Excellent
"Excellent front desk staff. Very helpful. "
Olivia 6-night trip
Posted 4 days ago
Hotel Trio Healdsburg

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 $90 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?

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 136 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.