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Healdsburg Vacation Rentals

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Jan 7 - Jan 8
Tomorrow
Jan 8 - Jan 9
This weekend
Jan 9 - Jan 11
Next weekend
Jan 16 - Jan 18

Our top choices for Healdsburg vacation rentals

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

Cottage in Forestville

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
Jan 11 - Jan 12
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

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.
$426 nightly
The price is $479
Jan 11 - Jan 12
Total with taxes and fees
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Dining
Cozy Riverfront Cabin - Beach Access & Wood Stove

Vacation Home in Guerneville

Cozy Riverfront Cabin - Beach Access & Wood Stove
9.8 out of 10, Exceptional, (13)
"Wonderful location and had everything we needed! "
United States
Maryrose H.
$442 nightly
The price is $497
Jan 11 - Jan 12
Total with taxes and fees
Cozy Riverfront Cabin - Beach Access & Wood Stove
TV, fireplace
Winemaker's Delight: 3BD/3BA Russian River Valley

Vacation Home in Northwest Santa Rosa

Winemaker's Delight: 3BD/3BA Russian River Valley
9.8 out of 10, Exceptional, (72)
"Comfortable beds and clean place. We enjoyed it"
United States
Amy F.
$441 nightly
The price is $496
Jan 11 - Jan 12
Total with taxes and fees
Winemaker's Delight: 3BD/3BA Russian River Valley
Outdoor pool, a heated pool
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Vacation Home in Healdsburg

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
10.0 out of 10, Exceptional, (66)
"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.
$1,945 nightly
The price is $2,150
Jan 11 - Jan 12
Total with taxes and fees
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Exterior
Enchanting Retreat in the heart of Redwoods

Mobile Home in Guerneville

Enchanting Retreat in the heart of Redwoods
8.8 out of 10, Excellent, (12)
"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.
$291 nightly
The price is $322
Jan 8 - Jan 9
Total with taxes and fees
Enchanting Retreat in the heart of Redwoods
Dining
Russian River Brew-cation Home

Vacation Home in Northwest Santa Rosa

Russian River Brew-cation Home
10.0 out of 10, Exceptional, (55)
"This house was perfect for our wine/beer getaway. The house was spacious, the kitchen had everything you need, and the beds were very comfortable. We also loved the view from the back porch spending each morning there with a cup of coffee. The location to everything was fantastic. It was a short drive to many wineries, breweries, and restaurants. We would definitely stay here again!!"
United States
Carol H.
$459 nightly
The price is $516
Jan 14 - Jan 15
Total with taxes and fees
Russian River Brew-cation Home
Dining
Sonoma Getaway: Winemaker’s Home with Modern Amenities

Vacation Home in Northwest Santa Rosa

Sonoma Getaway: Winemaker’s Home with Modern Amenities
10.0 out of 10, Exceptional, (77)
"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.
$467 nightly
The price is $525
Jan 14 - Jan 15
Total with taxes and fees
Sonoma Getaway: Winemaker’s Home with Modern Amenities
Fridge, microwave, oven, stovetop
Wineries & Wine: A Comforting Getaway in Wine Country

Vacation Home in Northwest Santa Rosa

Wineries & Wine: A Comforting Getaway in Wine Country
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.
$318 nightly
The price is $357
Jan 8 - Jan 9
Total with taxes and fees
Wineries & Wine: A Comforting Getaway in Wine Country
Property grounds
Redwoods getaway w/ decks & fenced yard

Vacation Home in Guerneville

Redwoods getaway w/ decks & fenced yard
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.
Redwoods getaway w/ decks & fenced yard
Terrace/patio
Vineyard Oasis: Luxury Home in the Heart of Sonoma.

Vacation Home in Healdsburg

Vineyard Oasis: Luxury Home in the Heart of Sonoma.
10.0 out of 10, Exceptional, (8)
"Kitchen was great, easy area for our dog.."
United States
Brad G.
$362 nightly
The price is $400
Jan 13 - Jan 14
Total with taxes and fees
Vineyard Oasis: Luxury Home in the Heart of Sonoma.
Property grounds
Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar

Villa in Geyserville

Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar
2.5 star property
9.2 out of 10, Wonderful, (14)
"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.
$1,047 nightly
The price is $1,157
Jan 27 - Jan 28
Total with taxes and fees
Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar
Interior
Walk to Russian River - Casa Del Rio - Unit A

Vacation Home in Forestville

Walk to Russian River - Casa Del Rio - Unit A
9.2 out of 10, Wonderful, (38)
"Impressed with how close it is in walking distance to the water really appreciated the gated parking area. "
United States
Sheree L.
Walk to Russian River - Casa Del Rio - Unit A
Villa, 6 Bedrooms | Exterior
Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa

Villa in Geyserville

Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa
3.5 star property
$1,112 nightly
The price is $1,130
Jan 20 - Jan 21
Total with taxes and fees
Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa
Property grounds
NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River

Apartment in Guerneville

NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River
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
Jan 8 - Jan 9
Total with taxes and fees
NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River
A heated pool
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6

Condo in Windsor

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
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.
$337 nightly
The price is $373
Jan 8 - Jan 9
Total with taxes and fees
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Exterior detail
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country

Vacation Home in Healdsburg

Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
9.6 out of 10, Exceptional, (64)
"This property is fantastic and the photos/listing don’t do it justice! It’s a little slice of heaven in wine country. On a small picturesque vineyard, the backdrop is already set for a perfect stay in wine country. The landscaping in the back yard is gorgeous. The house is very clean and comfortable, and had ample space for our group. It’s located a stone’s throw away from many great wineries in Healdsburg, making tastings super convenient. The host was kind and gracious and sent all the...
United States
Justin S.
$1,590 nightly
The price is $1,757
Jan 8 - Jan 9
Total with taxes and fees
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
TV, fireplace, books, offices
Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C

Cabin in Forestville

Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
$517 nightly
The price is $581
Jan 13 - Jan 14
Total with taxes and fees
Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
A heated pool
Farpoint: Heated Infinity Pool, Mountain Views

Vacation Home in Santa Rosa

Farpoint: Heated Infinity Pool, Mountain Views
9.8 out of 10, Exceptional, (8)
"Great location with lots of amenities. Very calming atmosphere. Very attentive staff. Can’t wait to go back."
United States
Christy
$773 nightly
The price is $858
Jan 13 - Jan 14
Total with taxes and fees
Farpoint: Heated Infinity Pool, Mountain Views
Interior
Creekside Under the Redwoods

Mobile Home in Guerneville

Creekside Under the Redwoods
9.8 out of 10, Exceptional, (17)
"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
$308 nightly
The price is $341
Jan 11 - Jan 12
Total with taxes and fees
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

Find out more about Healdsburg

Everything you need to know about Healdsburg vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’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 …and on.

There’s just as wide a choice of amenities, too. Maybe you’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 you’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. You’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 want—and just like that, you’ve built your dream Healdsburg vacation.

If you’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 top-notch restaurants and wineries.

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 140 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.