Healdsburg vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

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Popular amenities for Healdsburg vacation rentals

Stay near Healdsburg's top sights

Healdsburg Plaza47 locals recommend
Healdsburg Veterans Memorial Beach5 locals recommend
Bravas Bar de Tapas68 locals recommend
Willi's | Seafood & Raw Bar76 locals recommend
Big John's Market43 locals recommend
Healdsburg Bar & Grill24 locals recommend

Healdsburg home rentals

Guest favorite
Home in Healdsburg
Healdsburg Garden House
Dec 28 – Jan 4
$197 per night
4.92 out of 5 average rating, 517 reviews
Superhost
Home in Healdsburg
Peaceful location, hot tub, fire pit, game room!
Aug 28 – Sep 4
$384 per night
4.89 out of 5 average rating, 292 reviews
Guest favorite
Home in Healdsburg
The Wine Ranch
Nov 12 – 19
$370 per night
4.92 out of 5 average rating, 234 reviews
Guest favorite
Home in Windsor
Winelight Vineyard Home With Spa
Dec 6 – 13
$191 per night
4.96 out of 5 average rating, 376 reviews
Guest favorite
Home in Graton
Eco Luxury Private Sanctuary / The Farmhouse Oasis
Dec 12 – 19
$406 per night
5.0 out of 5 average rating, 557 reviews
Guest favorite
Home in Windsor
Luxury Wine Country Estate with pool & hot tub
Sep 1 – 8
$564 per night
4.99 out of 5 average rating, 136 reviews
Guest favorite
Home in Santa Rosa
Sunshine cottage
Sep 6 – 13
$135 per night
4.89 out of 5 average rating, 227 reviews
Guest favorite
Home in Windsor
Gorgeous Victorian in the HEART of Windsor
May 7 – 14
$383 per night
4.99 out of 5 average rating, 101 reviews

Healdsburg cottage rentals

Guest favorite
Cottage in Healdsburg
Bee Haven Cottage
Oct 9 – 16
$258 per night
5.0 out of 5 average rating, 156 reviews
Superhost
Cottage in Sebastopol
Stunning Sauna Cottage Retreat on Private Vineyard
Jan 19 – 26
$252 per night
4.92 out of 5 average rating, 198 reviews
Guest favorite
Cottage in Windsor
Vineyard Cozy Cottage & Hot Tub
Dec 11 – 18
$174 per night
5.0 out of 5 average rating, 116 reviews
Guest favorite
Cottage in Cloverdale
Asti Ridge Ranch - Private One Bedroom Cottage
Jul 22 – 29
$185 per night
4.97 out of 5 average rating, 112 reviews
Guest favorite
Cottage in Sebastopol
Designer Wine Country Cottage in Perfect Location
Jun 21 – 28
$274 per night
4.99 out of 5 average rating, 154 reviews
Guest favorite
Cottage in Healdsburg
❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
Jun 3 – 10
$556 per night
4.95 out of 5 average rating, 106 reviews
Guest favorite
Cottage in Sonoma
Modern Farmhouse on Vineyard w Deck + Bocce Court
Jan 3 – 10
$325 per night
4.99 out of 5 average rating, 139 reviews
Superhost
Cottage in Forestville
Nestled in Nature
May 12 – 19
$260 per night
4.92 out of 5 average rating, 303 reviews

Other great vacation rentals in Healdsburg

Guest favorite
Guest suite in Healdsburg
Pony Ranch Vineyard Estate with Pool
Apr 25 – May 2
$194 per night
4.92 out of 5 average rating, 408 reviews
Guest favorite
Guesthouse in Healdsburg
Bunkhouse at Side Road Farm
Aug 16 – 23
$242 per night
4.99 out of 5 average rating, 208 reviews
Guest favorite
Guest suite in Windsor
Private Entrance Suite in Heart of Wine Country
Aug 12 – 19
$112 per night
4.98 out of 5 average rating, 353 reviews
Guest favorite
Guesthouse in Healdsburg
Healdsburg Cottage-Workspace, Walk to Plaza
Feb 20 – 27
$282 per night
4.93 out of 5 average rating, 298 reviews
Guest favorite
Guesthouse in Santa Rosa
Wine Country guest house
Jul 8 – 15
$93 per night
4.89 out of 5 average rating, 674 reviews
Guest favorite
Guesthouse in Sebastopol
Lemon Moon Cottage
Jul 31 – Aug 5
$129 per night
4.9 out of 5 average rating, 1106 reviews
Guest favorite
Guest suite in Forestville
Forest Gem: peaceful retreat in the woods
Aug 11 – 18
$150 per night
4.97 out of 5 average rating, 150 reviews
Guest favorite
Apartment in Sebastopol
Amy's Local BNB - walk to town **and hot tub!**
Sep 5 – 12
$132 per night
4.99 out of 5 average rating, 600 reviews

Quick stats about vacation rentals in Healdsburg

Total rentals

100 properties

Rentals with a pool

20 properties have a pool

Pet-friendly rentals

40 properties allow pets

Family-friendly rentals

70 properties are a good fit for families

Total number of reviews

4.1K reviews

Nightly prices starting at

$80 before taxes and fees

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Healdsburg?

    Yes! Work meets play with ease at over 60 vacation rentals in Healdsburg featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Healdsburg?

    Four-legged friends are welcome in Healdsburg. Choose from more than 40 vacation rentals for guests traveling with pets.

  • Are there Healdsburg vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Healdsburg, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in house rentals in Healdsburg?

    Experience the best of Healdsburg with our house rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly vacation rentals in Healdsburg?

    Healdsburg has more than 70 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Healdsburg have a bbq area?

    Absolutely! We offer over 30 house rentals with a bbq area in Healdsburg. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Healdsburg have self check-in?

    Absolutely! We offer over 10 house rentals with self check-in in Healdsburg. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Healdsburg?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with a bbq area, over 10 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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  2. United States
  3. California
  4. Sonoma County
  5. Healdsburg