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.
Guesthouse in Sebastopol
4.93 out of 5 average rating, 674 reviewsSun Drenched Flat
Put up the burnt-orange parasol and settle down with book on the patio while the barbecue heats up. Sitting above a garage in a serene, walkable neighborhood, this sunlit retreat's beachy cream painted paneling gives it a chilled, refined vibe. Check out all that Sebastopol has to offer at: visitsebastopolnow.come This second story house is a very desirable space, located close to town, still being set on a very beautiful street in an friendly established older neighborhood. It is nestled between other structures on the property. One being a "Tiny House" that is right next door, my home sits behind the flat. The house has a full kitchen with all the utensils and necessary cooking items, pots pans etc. Large toaster oven that will even fit your frozen pizza. There is a space in front with some Adirondack chairs and BBQ if you want to relax outside. The house has its own separate entrance off the driveway. My house is in back of the flat, I may or may not see you, but I am available for any questions at any time. You will more than likely be greeted by our white cat with orange tips (named White Boy). If he gets a chance, Charlie our very exuberant Golden Doodle will give you a warm excited welcome. Located just 1 mile from the heart of the sweet town of Sebastopol, this area is a handy stepping off point to explore nearby wineries, scenic beaches, and shopping and restaurants at redwoods. A very nice mile walk to town or a five minute drive. There is a flight of stairs that you climb to get to the Flat space, it does not have wheelchair access. There are cats on the property, but they do not go inside the flat. Our Goldendoodle is extremely friendly. The leather couch folds flat into a double bed for accommodating two more guests. Access to the bathroom is through the bedroom however. There is no dedicated parking, however the street parking directly across from the flat, just up from, but not in front of the three mailboxes is usually always open.
Jul 1 – 8
Guesthouse in Healdsburg
4.98 out of 5 average rating, 177 reviewsHealdsburg Contemporary Cottage With Lush Backyard Patio
Stay in shape in the fully equipped Pilates studio, Afterwards, freshen up in the skylighted shower room with heated stone floor. Later, enjoy a glass of wine and a good book in the outdoor lounge and dine alfresco in the landscaped garden. The perfect home away from home. Makes this your personal sanctuary wether you are staying for the weekend or for the whole month while looking for the perfect home to buy. Well appointed, decorated with international contemporary art with just enough touches that take you beyond the hotel luxury suite. A great modern getaway with Garden, al fresco dining with BBQ, garden lounge area and fully equipped Pilates Studio. Park right in front of your guest house with private gated entry to your personal cottage. I am happy to help you plan your Healdsburg and Wine country excursions. From restaurants and wineries along with the perfect biking routes, top classical dressage lessons on Lusitanos or private Art Studio Tour, Pilates training at the on site studio, massage in the Guest house, Culinary Tour, Farmers Market to Picnic at Music on the Square on Tuesdays.... Head out for an easy stroll to downtown and the Plaza area, with boutiques, galleries, and antique shops to browse. Stock up at the farmers' market, sample local vintages in wine-tasting rooms, and dine at a wide choice of chic restaurants. Within easy walking distance to downtown Restaurants, Wine Tasting Rooms, Galleries, Antique Shops, Spas, Boutiques and Farmers Market. Healdsburg Contemporary Cottages is registered with the City of Healdsburg and is collecting TOT Taxes of 16% for the City of Healdsburg which are included in the pricing. The Business License Number is: (PHONE NUMBER HIDDEN)
Oct 17 – 24
Home in Healdsburg
4.96 out of 5 average rating, 429 reviewsDry Creek Valley Cottage
Enjoy your stay in beautiful Dry Creek Valley, a pastoral rural setting surrounded by vineyards and local wineries, minutes from Healdsburg's historic quaint downtown plaza. The cottage is 480 square feet with big windows, high ceilings and its own private entrance. There is parking right in front. It has kitchen amenities (coffee and tea pot, mini refrigerator, toaster and microwave), living room and bathroom with a mosaic tile shower. Right across the way you can take a lovely walk or run alongside the vineyards or you can rent a bike to explore the beauty of the valley. If you enjoy hiking, seasonal kayaking or canoeing there are opportunities all around us to explore as well. Our property has multiple fruit trees and we will be happy to share whatever bounty is in season when you arrive. The water here is also clean spring fed and very tasty and the sky at night is full of stars! You can enjoy sitting in the front yard which is bordered by a dozen Redwood trees or you can picnic in our big back yard among the fruit trees. We also have 2 female dogs who are quite friendly if you'd like to meet them. We would be happy to welcome you to Sonoma County and insure that your stay here is enjoyable.
Mar 26 – Apr 2
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Healdsburg vacation rentals
Healdsburg home rentals
Home in Healdsburg
4.93 out of 5 average rating, 522 reviewsHealdsburg Garden House
Nov 25 – Dec 2
Home in Healdsburg
4.89 out of 5 average rating, 292 reviewsPeaceful location, hot tub, fire pit, game room!
Apr 20 – 27
Home in Graton
5.0 out of 5 average rating, 556 reviewsEco Luxury Private Sanctuary / The Farmhouse Oasis
Oct 16 – 23
Home in Healdsburg
4.92 out of 5 average rating, 234 reviewsThe Wine Ranch
Nov 5 – 12
Home in Sonoma
4.95 out of 5 average rating, 394 reviewsZen House on 15 acres
Jul 26 – Aug 2
Home in Cazadero
4.95 out of 5 average rating, 114 reviewsRanch Stay for 2
Jan 19 – 26
Home in Sebastopol
4.96 out of 5 average rating, 362 reviewsSebastopol Guest House
Jun 6 – 13
Home in Windsor
4.99 out of 5 average rating, 101 reviewsGorgeous Victorian in the HEART of Windsor
Sep 6 – 13
Home in Windsor
4.96 out of 5 average rating, 377 reviewsWinelight Vineyard Home With Spa
Dec 26 – Jan 2
Home in Windsor
4.99 out of 5 average rating, 139 reviewsLuxury Wine Country Estate with pool & hot tub
Sep 8 – 15
Home in Sonoma
4.99 out of 5 average rating, 115 reviewsEasy elegance in this wine country home
Jul 24 – 31
Home in Forestville
4.99 out of 5 average rating, 251 reviewsSomms Rest Designed Curated Peaceful
Apr 14 – 21
Healdsburg cottage rentals
Cottage in Healdsburg
5.0 out of 5 average rating, 157 reviewsBee Haven Cottage
Jul 25 – Aug 1
Cottage in Sebastopol
4.92 out of 5 average rating, 200 reviewsStunning Sauna Cottage Retreat on Private Vineyard
Dec 31 – Jan 7
Cottage in Cloverdale
4.97 out of 5 average rating, 112 reviewsAsti Ridge Ranch - Private One Bedroom Cottage
Apr 29 – May 6
Cottage in Sebastopol
4.99 out of 5 average rating, 156 reviewsDesigner Wine Country Cottage in Perfect Location
Oct 31 – Nov 7
Cottage in Windsor
5.0 out of 5 average rating, 117 reviewsVineyard Cozy Cottage & Hot Tub
Dec 20 – 27
Cottage in Sonoma
4.99 out of 5 average rating, 140 reviewsModern Farmhouse on Vineyard w Deck + Bocce Court
Feb 3 – 10
Cottage in Healdsburg
4.95 out of 5 average rating, 108 reviews❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
Jun 29 – Jul 6
Cottage in Forestville
4.94 out of 5 average rating, 406 reviewsCosmo Beach River-front Sanctuary
Aug 2 – 9
Cottage in Forestville
4.92 out of 5 average rating, 303 reviewsNestled in Nature
May 29 – Jun 5
Cottage in Jenner
4.99 out of 5 average rating, 350 reviewsRiverfront Serenity on the Sonoma Coast
Nov 12 – 19
Cottage in Occidental
4.96 out of 5 average rating, 557 reviewsThe Perch
Apr 3 – 10
Cottage in Sebastopol
4.98 out of 5 average rating, 113 reviewsUnique Wine Country~Garden Gem
Jun 14 – 21
Other great vacation rentals in Healdsburg
Guest suite in Forestville
4.97 out of 5 average rating, 152 reviewsForest Gem: peaceful retreat hot tub and firepit
May 15 – 22
Loft in Windsor
4.81 out of 5 average rating, 499 reviewsThe Loft Under The Oaks
Nov 21 – 28
Guesthouse in Santa Rosa
4.89 out of 5 average rating, 674 reviewsWine Country guest house
Sep 28 – Oct 5
Guesthouse in Healdsburg
4.94 out of 5 average rating, 285 reviewsTh Roost - Sun Room
Mar 3 – 10
Guesthouse in Healdsburg
4.99 out of 5 average rating, 208 reviewsBunkhouse at Side Road Farm
Jul 17 – 24
Apartment in Sebastopol
4.99 out of 5 average rating, 601 reviewsAmy's Local BNB - walk to town **and hot tub!**
Aug 21 – 28
Guesthouse in Healdsburg
4.93 out of 5 average rating, 299 reviewsHealdsburg Cottage-Workspace, Walk to Plaza
Oct 16 – 23
Guesthouse in Sebastopol
4.9 out of 5 average rating, 1107 reviewsLemon Moon Cottage
Feb 9 – 14
Apartment in Santa Rosa
4.97 out of 5 average rating, 755 reviewsPrivate Getaway in West Santa Rosa
Nov 17 – 24
Guest suite in Sebastopol
5.0 out of 5 average rating, 344 reviews#1 Host In CA: Modern. Serene. Spectacular Views!
Mar 3 – 10
Guesthouse in Sebastopol
4.96 out of 5 average rating, 289 reviewsArbor View
Jun 18 – 25
Guesthouse in Healdsburg
4.96 out of 5 average rating, 101 reviewsDog Friendly Healdsburg / Dry Creek Valley Cottage
Mar 9 – 16
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 10 homes with self check-in, over 30 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
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