Photo by Ardilla Mexicano

Healdsburg Holiday Rentals

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
14 Jan - 15 Jan
Tomorrow
15 Jan - 16 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

Our top choices for Healdsburg holiday rentals

Outdoor dining

Cabin in Guerneville

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
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 HK$1,193
HK$3,766 total
includes taxes & fees
20 Jan - 21 Jan
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Outdoor dining

Cottage in Forestville

True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
10.0 out of 10, Exceptional, (11 reviews)
"Ideal for a relaxing time in wine country! The winery on property is fantastic and highly recommend it!"
United States
Paul H.
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Dining

Holiday Home in Guerneville

Cozy Riverfront Cabin - Beach Access & Wood Stove
9.8 out of 10, Exceptional, (13 reviews)
"Wonderful location and had everything we needed! "
United States
Maryrose H.
The price is HK$1,108
HK$3,907 total
includes taxes & fees
19 Jan - 20 Jan
Cozy Riverfront Cabin - Beach Access & Wood Stove
Fridge, microwave, oven, stovetop

Holiday Home in Northwest Santa Rosa

Wineries & Wine: A Comforting Getaway in Wine Country
9.4 out of 10, Exceptional, (22 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 HK$850
HK$2,665 total
includes taxes & fees
19 Jan - 20 Jan
Wineries & Wine: A Comforting Getaway in Wine Country
TV, fireplace

Holiday Home in Northwest Santa Rosa

Winemaker's Delight: 3BD/3BA Russian River Valley
9.8 out of 10, Exceptional, (72 reviews)
"Comfortable beds and clean place. We enjoyed it"
United States
Amy F.
The price is HK$1,318
HK$3,531 total
includes taxes & fees
9 Feb - 10 Feb
Winemaker's Delight: 3BD/3BA Russian River Valley
Exterior

Mobile Home in Guerneville

Enchanting Retreat in the heart of Redwoods
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 HK$1,179
HK$2,495 total
includes taxes & fees
2 Feb - 3 Feb
Enchanting Retreat in the heart of Redwoods
Outdoor pool, a heated pool

Holiday Home in Healdsburg

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
10.0 out of 10, Exceptional, (66 reviews)
"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.
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Interior

Holiday Home in Healdsburg

Private Vineyard-View Wine Country Home Near Healdsburg and Sonoma Wineries
10.0 out of 10, Exceptional, (8 reviews)
"Kitchen was great, easy area for our dog.."
United States
Brad G.
The price is HK$1,397
HK$3,099 total
includes taxes & fees
20 Jan - 21 Jan
Private Vineyard-View Wine Country Home Near Healdsburg and Sonoma Wineries
Exterior

Villa in Geyserville

Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa
3.5 star property
The price is HK$3,636
HK$9,005 total
includes taxes & fees
20 Jan - 21 Jan
Adventure Alexander Valley Lodge With Pool & Hot Tub 6 Bedroom Villa
Dining

Holiday Home in Northwest Santa Rosa

Sonoma Getaway: Winemaker’s Home with Modern Amenities
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 HK$1,506
HK$3,812 total
includes taxes & fees
12 Feb - 13 Feb
Sonoma Getaway: Winemaker’s Home with Modern Amenities
Dining

Holiday Home in Northwest Santa Rosa

Russian River Brew-cation Home
10.0 out of 10, Exceptional, (55 reviews)
"The house was great! We enjoyed our stay"
United States
Warren M.
The price is HK$1,482
HK$3,851 total
includes taxes & fees
2 Feb - 3 Feb
Russian River Brew-cation Home
TV, fireplace, books, offices

Cabin in Forestville

Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
The price is HK$1,622
HK$4,555 total
includes taxes & fees
20 Jan - 21 Jan
Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
A heated pool

Condo in Windsor

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
9.2 out of 10, Wonderful, (43 reviews)
"Check-in was a little difficult, but the condo itself was convenient and a great stay."
United States
SB L.
The price is HK$1,560
HK$2,931 total
includes taxes & fees
22 Jan - 23 Jan
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Property grounds

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, (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 HK$4,842
HK$8,935 total
includes taxes & fees
27 Jan - 28 Jan
Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar
Property grounds

Apartment in Guerneville

NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River
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 HK$1,731
HK$2,525 total
includes taxes & fees
16 Jan - 17 Jan
NEW Contemporary Guest-Suite by Robaire in Guerneville/Rio Nido/Russian River
Exterior detail

Holiday Home in Healdsburg

Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
9.6 out of 10, Exceptional, (65 reviews)
"Better than expected!! We loved this properly and would most definitely stay again!! It was perfect and magical in every way!!! "
United States
Elaine G.
The price is HK$11,199
HK$17,348 total
includes taxes & fees
18 Jan - 19 Jan
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
Pool

Villa in Geyserville

NEW! Adventure Alexander Valley Lodge with Pool & Hot tub
2.0 star property
The price is HK$4,261
HK$9,511 total
includes taxes & fees
20 Jan - 21 Jan
NEW! Adventure Alexander Valley Lodge with Pool & Hot tub
A heated pool

Holiday Home in Santa Rosa

Farpoint: Heated Infinity Pool, Mountain Views
9.8 out of 10, Exceptional, (9 reviews)
"Great location with lots of amenities. Very calming atmosphere. Very attentive staff. Can’t wait to go back."
United States
Christy
The price is HK$3,159
HK$6,690 total
includes taxes & fees
19 Jan - 20 Jan
Farpoint: Heated Infinity Pool, Mountain Views
Exterior

Villa in Healdsburg

Luxury Hilltop Villa | Pool, Hot Tub & Close to Downtown
The price is HK$6,912
HK$13,642 total
includes taxes & fees
20 Jan - 21 Jan
Luxury Hilltop Villa | Pool, Hot Tub & Close to Downtown
Interior

Mobile Home in Guerneville

Creekside Under the Redwoods
9.8 out of 10, Exceptional, (17 reviews)
"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 traveller
The price is HK$1,314
HK$2,661 total
includes taxes & fees
28 Jan - 29 Jan
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.
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

The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton

10/10 Excellent
"The young lady working reception was extremely friendly. Gave us a late checkout of one hour because medical circumstances delayed us."
BRIAN 1-night trip
Posted 3 days ago
The Lodge at Healdsburg, Tapestry Collection by Hilton

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 holiday rentals in Healdsburg?

Yes, there are holiday rentals in Healdsburg close to SingleThread Farm at Dry Creek, or you can select a more secluded option if you're looking for 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 are some of the best holiday rentals that Healdsburg has to offer?

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg: This highly rated holiday home rental in Healdsburg is located in a rural location, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Healdsburg?

Expedia has 141 holiday 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 holiday rentals like in Healdsburg?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Healdsburg. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family trip or a small group gathering.