Healdsburg Vacation Rentals

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Check prices for these dates

Tonight
Dec 24 - Dec 25
Tomorrow
Dec 25 - Dec 26
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Healdsburg vacation rentals

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

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

True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
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.
The price is ￥31,380
￥77,603 total
includes taxes & fees
Jan 15 - Jan 16, 2026
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Outdoor dining
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

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)
"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 ￥23,886
￥74,925 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Dining
Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (13)
"Wonderful location and had everything we needed! "
United States
Maryrose H.
The price is ￥28,870
￥86,415 total
includes taxes & fees
Dec 28 - Dec 29
Cozy Riverfront Cabin - Beach Access & Wood Stove
Interior
Creekside Under the Redwoods

Creekside Under the Redwoods

Creekside Under the Redwoods
Guerneville
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
The price is ￥26,303
￥53,752 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Creekside Under the Redwoods
Dining
Sonoma Getaway: Winemaker’s Home with Modern Amenities

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, (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.
The price is ￥26,697
￥70,678 total
includes taxes & fees
Dec 28 - Dec 29
Sonoma Getaway: Winemaker’s Home with Modern Amenities
Outdoor pool, a heated pool
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
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.
The price is ￥282,420
￥445,596 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Interior
Walk to Russian River - Casa Del Rio - Unit A

Walk to Russian River - Casa Del Rio - Unit A

Walk to Russian River - Casa Del Rio - Unit A
Forestville
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.
The price is ￥27,992
￥74,285 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Walk to Russian River - Casa Del Rio - Unit A
TV, fireplace
Winemaker's Delight: 3BD/3BA Russian River Valley

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)
"Comfortable beds and clean place. We enjoyed it"
United States
Amy F.
The price is ￥26,228
￥68,198 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Winemaker's Delight: 3BD/3BA Russian River Valley
Fridge, microwave, oven, stovetop
Wineries & Wine: A Comforting Getaway in Wine Country

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, (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.
The price is ￥21,076
￥57,054 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Wineries & Wine: A Comforting Getaway in Wine Country
Dining
Russian River Brew-cation Home

Russian River Brew-cation Home

Russian River Brew-cation Home
Northwest Santa Rosa
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.
The price is ￥23,886
￥67,331 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Russian River Brew-cation Home
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

NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River
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.
The price is ￥34,659
￥50,090 total
includes taxes & fees
Dec 27 - Dec 28
NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River
Terrace/patio
Vineyard Oasis: Luxury Home in the Heart of Sonoma.

Vineyard Oasis: Luxury Home in the Heart of Sonoma.

Vineyard Oasis: Luxury Home in the Heart of Sonoma.
Healdsburg
10.0 out of 10, Exceptional, (7)
"We had a great time!The house was perfect for our needs!"
United States
Theresa C.
The price is ￥27,961
￥62,022 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Vineyard Oasis: Luxury Home in the Heart of Sonoma.
Exterior
Puccioni Paradise | Wine Tastings Included

Puccioni Paradise | Wine Tastings Included

Puccioni Paradise | Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (2)
"Was a great stay. Very much appreciated the location, amenities and communication."
United States
Jill M.
The price is ￥33,659
￥111,290 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Puccioni Paradise | Wine Tastings Included
Villa, 6 Bedrooms | Exterior
Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa

Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa

Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa
3.5 star property
Geyserville
The price is ￥91,620
￥204,525 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa
Property grounds
Redwoods getaway w/ decks & fenced yard

Redwoods getaway w/ decks & fenced yard

Redwoods getaway w/ decks & fenced yard
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.
The price is ￥27,735
￥75,629 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Redwoods getaway w/ decks & fenced yard
A heated pool
Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views
Santa Rosa
9.8 out of 10, Exceptional, (7)
"Great location with lots of amenities. Very calming atmosphere. Very attentive staff. Can’t wait to go back."
United States
Christy
The price is ￥156,508
￥255,779 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Farpoint: Heated Infinity Pool, Mountain Views
Terrace/patio
Valley Vista | Wine Tastings Included

Valley Vista | Wine Tastings Included

Valley Vista | Wine Tastings Included
Guerneville
10.0 out of 10, Exceptional, (85)
"Clean, comfortable, well-appointed home with excellent outdoor space to relax. Included wine tasting was a plus!"
United States
Robert G.
The price is ￥46,082
￥128,186 total
includes taxes & fees
Dec 30 - Dec 31
Valley Vista | Wine Tastings Included
Exterior detail
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country

Luxury Private Estate at Zoella Vineyards in the heart of Wine Country

Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
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.
The price is ￥224,110
￥351,857 total
includes taxes & fees
Dec 30 - Dec 31
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
Outdoor dining
Luxurious Wine Country Oasis | Wine Tastings Included

Luxurious Wine Country Oasis | Wine Tastings Included

Luxurious Wine Country Oasis | Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (26)
"Awesome place and a great location!"
United States
Matt S.
The price is ￥103,727
￥232,603 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Luxurious Wine Country Oasis | Wine Tastings Included
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 Vinea, a Travelodge by Wyndham

Hotel Vinea, a Travelodge by Wyndham

10/10 Excellent
"♡"
Chloe 1-night trip
Posted 5 days ago
Hotel Vinea, a Travelodge by Wyndham

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
  • Use the map to find apartments and other holiday homes in the Healdsburg neighbourhood you prefer
  • 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 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.