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, 531 reviewsHealdsburg Garden House
Mar 21 – 28
Home in Healdsburg
4.91 out of 5 average rating, 127 reviewsDry Creek w/Hot Tub, Bocce, Vineyard Views
Jan 19 – 26
Home in Healdsburg
4.88 out of 5 average rating, 138 reviewsModern Home in Hburg Wine Country
Aug 31 – Sep 7
Home in Graton
5.0 out of 5 average rating, 565 reviewsEco Luxury Private Sanctuary / The Farmhouse Oasis
Jan 30 – Feb 6
Home in Healdsburg
4.92 out of 5 average rating, 239 reviewsThe Wine Ranch
Apr 1 – 8
Home in Healdsburg
4.89 out of 5 average rating, 297 reviewsPeaceful location, hot tub, fire pit, game room!
Mar 6 – 13
Home in Sonoma
4.95 out of 5 average rating, 401 reviewsZen House on 15 acres
Dec 5 – 12
Home in Windsor
5.0 out of 5 average rating, 101 reviewsLarge Home w/ HotTub 10 min to Downtown Healdsburg
Aug 22 – 29
Healdsburg cottage rentals
Cottage in Sebastopol
4.91 out of 5 average rating, 215 reviewsStunning Sauna Cottage Retreat on Private Vineyard
Feb 18 – 25
Cottage in Sebastopol
4.98 out of 5 average rating, 162 reviewsDesigner Wine Country Cottage in Perfect Location
Jan 21 – 28
Cottage in Cloverdale
4.97 out of 5 average rating, 114 reviewsAsti Ridge Ranch - Private One Bedroom Cottage
Oct 24 – 31
Cottage in Healdsburg
4.96 out of 5 average rating, 115 reviews❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
Jul 23 – 30
Cottage in Sonoma
4.99 out of 5 average rating, 150 reviewsModern Farmhouse on Vineyard w Deck + Bocce Court
Oct 17 – 24
Cottage in Windsor
5.0 out of 5 average rating, 124 reviewsVineyard Cozy Cottage & Hot Tub
Jun 28 – Jul 5
Cottage in Bodega Bay
4.98 out of 5 average rating, 846 reviewsKnix's Cabin at Salmon Creek
Apr 27 – May 4
Cottage in Jenner
4.99 out of 5 average rating, 359 reviewsRiverfront Serenity on the Sonoma Coast
Jan 16 – 23
Other great vacation rentals in Healdsburg
Guest suite in Forestville
4.97 out of 5 average rating, 161 reviewsForest Gem: peaceful retreat hot tub and firepit
Oct 11 – 18
Loft in Windsor
4.81 out of 5 average rating, 501 reviewsThe Loft Under The Oaks
Nov 2 – 9
Guesthouse in Healdsburg
4.93 out of 5 average rating, 299 reviewsHealdsburg Cottage-Workspace, Walk to Plaza
Nov 28 – Dec 5
Guesthouse in Healdsburg
4.96 out of 5 average rating, 101 reviewsDog Friendly Healdsburg / Dry Creek Valley Cottage
Jul 16 – 23
Guesthouse in Healdsburg
4.99 out of 5 average rating, 210 reviewsBunkhouse at Side Road Farm
Oct 23 – 30
Apartment in Sebastopol
4.99 out of 5 average rating, 609 reviewsAmy's Local BNB - walk to town **and hot tub!**
Oct 13 – 20
Apartment in Santa Rosa
4.97 out of 5 average rating, 767 reviewsPrivate Getaway in West Santa Rosa
Feb 11 – 18
Guesthouse in Sebastopol
4.9 out of 5 average rating, 1122 reviewsLemon Moon Cottage
Sep 24 – 29
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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