Holiday rentals in Healdsburg

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Healdsburg

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Guest house in Sebastopol

4.93 out of 5 average rating, 674 reviews

Sun 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.

1–8 Jul

₹11,449 per night
Guest favourite

Guest house in Healdsburg

4.98 out of 5 average rating, 177 reviews

Healdsburg 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)

17–24 Oct

₹60,238 per night
Guest favourite

Home in Healdsburg

4.96 out of 5 average rating, 429 reviews

Dry 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.

26 Mar – 2 Apr

₹16,423 per night

Popular amenities for Healdsburg holiday 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

Other great holiday rentals in Healdsburg

Guest favourite

Loft in Windsor

4.81 out of 5 average rating, 499 reviews

The Loft Under The Oaks

21–28 Nov

₹11,519 per night
Guest favourite

Cottage in Healdsburg

5.0 out of 5 average rating, 157 reviews

Bee Haven Cottage

25 Jul – 1 Aug

₹24,669 per night
Guest favourite

Guest suite in Forestville

4.97 out of 5 average rating, 151 reviews

Forest Gem: peaceful retreat hot tub and firepit

15–22 May

₹12,822 per night
Guest favourite

Guest house in Santa Rosa

4.89 out of 5 average rating, 674 reviews

Wine Country guest house

28 Sep – 5 Oct

₹8,977 per night
Guest favourite

Cottage in Cloverdale

4.97 out of 5 average rating, 112 reviews

Asti Ridge Ranch - Private One Bedroom Cottage

29 Apr – 6 May

₹14,086 per night
Superhost

Cottage in Sebastopol

4.92 out of 5 average rating, 200 reviews

Stunning Sauna Cottage Retreat on Private Vineyard

31 Dec – 7 Jan

₹24,145 per night
Guest favourite

Home in Healdsburg

4.93 out of 5 average rating, 522 reviews

Healdsburg Garden House

25 Nov – 2 Dec

₹18,843 per night
Guest favourite

Guest house in Healdsburg

4.94 out of 5 average rating, 285 reviews

Th Roost - Sun Room

5–12 May

₹28,238 per night
Guest favourite

Cottage in Healdsburg

4.95 out of 5 average rating, 108 reviews

❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤

29 Jun – 6 Jul

₹68,757 per night
Guest favourite

Guest house in Healdsburg

4.99 out of 5 average rating, 208 reviews

Bunkhouse at Side Road Farm

17–24 Jul

₹21,002 per night
Guest favourite

Home in Healdsburg

5.0 out of 5 average rating, 49 reviews

10 Acre Vineyard Cottage w/Hot Tub + Bocce Court

17–24 Nov

₹27,758 per night
Guest favourite

Bungalow in Healdsburg

5.0 out of 5 average rating, 7 reviews

HBG Fitch House - 3 block walk to Downtown 30+days

1–8 Sep

₹13,493 per night

Quick stats about holiday 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

4.1T reviews

Nightly prices starting at

₹6,668 before taxes and fees

Destinations to explore

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