Healdsburg vacation rentals
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Top-rated vacation rentals in Healdsburg
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Healdsburg vacation rentals
Other great vacation rentals in Healdsburg
Home in Healdsburg
4.93 out of 5 average rating, 526 reviewsHealdsburg Garden House
Jan 1 – 8
Home in Healdsburg
4.98 out of 5 average rating, 396 reviewsVineyard Modern Barn House - Dry Creek Valley
Jan 5 – 12
Home in Healdsburg
4.91 out of 5 average rating, 126 reviewsDry Creek w/Hot Tub, Bocce, Vineyard Views
Feb 3 – 10
Home in Healdsburg
4.92 out of 5 average rating, 236 reviewsThe Wine Ranch
Feb 11 – 18
Home in Healdsburg
4.89 out of 5 average rating, 294 reviewsPeaceful location, hot tub, fire pit, game room!
Aug 30 – Sep 6
Home in Sonoma
4.95 out of 5 average rating, 397 reviewsZen House on 15 acres
Sep 8 – 15
Home in Windsor
4.96 out of 5 average rating, 378 reviewsWinelight Vineyard Home With Spa
Feb 23 – Mar 2
Home in Graton
5.0 out of 5 average rating, 561 reviewsEco Luxury Private Sanctuary / The Farmhouse Oasis
Oct 9 – 16
Healdsburg cottage rentals
Cottage in Healdsburg
5.0 out of 5 average rating, 158 reviewsBee Haven Cottage
Dec 16 – 23
Cottage in Sebastopol
4.91 out of 5 average rating, 209 reviewsStunning Sauna Cottage Retreat on Private Vineyard
Jan 7 – 14
Cottage in Sebastopol
4.99 out of 5 average rating, 158 reviewsDesigner Wine Country Cottage in Perfect Location
Oct 25 – Nov 1
Cottage in Healdsburg
4.96 out of 5 average rating, 112 reviews❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
Aug 13 – 20
Cottage in Cloverdale
4.97 out of 5 average rating, 113 reviewsAsti Ridge Ranch - Private One Bedroom Cottage
Sep 25 – Oct 2
Cottage in Windsor
5.0 out of 5 average rating, 120 reviewsVineyard Cozy Cottage & Hot Tub
Feb 16 – 23
Cottage in Sonoma
4.99 out of 5 average rating, 145 reviewsModern Farmhouse on Vineyard w Deck + Bocce Court
Oct 5 – 12
Cottage in Forestville
4.92 out of 5 average rating, 309 reviewsNestled in Nature
Jun 14 – 21
Other great vacation rentals in Healdsburg
Guesthouse in Sebastopol
4.93 out of 5 average rating, 678 reviewsSun Drenched Flat
Nov 15 – 22
Guest suite in Forestville
4.97 out of 5 average rating, 158 reviewsForest Gem: peaceful retreat hot tub and firepit
May 29 – Jun 5
Guesthouse in Healdsburg
4.99 out of 5 average rating, 209 reviewsBunkhouse at Side Road Farm
Jun 11 – 18
Guesthouse in Healdsburg
4.96 out of 5 average rating, 101 reviewsDog Friendly Healdsburg / Dry Creek Valley Cottage
Mar 19 – 26
Guesthouse in Santa Rosa
4.89 out of 5 average rating, 675 reviewsWine Country guest house
Oct 27 – Nov 3
Apartment in Sebastopol
4.99 out of 5 average rating, 608 reviewsAmy's Local BNB - walk to town **and hot tub!**
Aug 25 – Sep 1
Guesthouse in Healdsburg
4.93 out of 5 average rating, 299 reviewsHealdsburg Cottage-Workspace, Walk to Plaza
Nov 21 – 28
Apartment in Santa Rosa
4.97 out of 5 average rating, 762 reviewsPrivate Getaway in West Santa Rosa
Jan 18 – 25
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
4.3K 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 wifi?
Absolutely! We offer over 50 house rentals with wifi in Healdsburg. Enjoy a tailored experience with all the comforts you desire.
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.
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