Holiday rentals in Healdsburg

4.95 out of 5 average rating, 460 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.

4.98 out of 5 average rating, 291 reviews

Alexander Valley: Wine Lover and Cycling Paradise

The Finca Guest House is a beautiful modern & private unit, which offers country seclusion just a short hop into Healdsburg. Three private outdoor spaces for your use! Coffee patio, wine patio, goat patio--your choice! World-class biking out the door. Guest House will be thoroughly cleaned per Airbnb guidelines! *This property has farm animals so no outside animals allowed. See Rules and Policies notes Gas grill w/burner is available for outdoor cooking. NO full kitchen. Sonoma Co. TOT#3191N

Guest suite in Healdsburg

4.93 out of 5 average rating, 442 reviews

Pony Ranch Vineyard Estate with Pool

Guest House with private entrance on gorgeous gated Vineyard Estate. Overlooks pool and vineyards with views to Mount St. Helena. Gas fireplace, refrigerator, microwave, Keurig coffee maker, queen bed. Seasonal private pool with fabulous views, occasionally shared with owners. Toilet and sink separate from shower. 8 minutes to the Healdsburg Plaza. Less than a mile from 3 wineries, very close to dozens more. Agricultural Education Programs available. Sonoma County TOT Certificate 1362N

4.93 out of 5 average rating, 590 reviews

Healdsburg Garden House

Enjoy a real Sonoma County Experience Best Value in the Valley Organic grapes, hops, flower and vegetable gardens Centrally located home away from home Large Covered Redwood Deck with Gas Grill NEW A/C and Heating (controls in each bedroom) Super clean and sanitized Private, spacious & comfortable Fully Stocked Kitchen w/ Dishwasher 50” HDTV’s in each room (HBO, Showtime, Netflix, YouTube…) 1 GB High Speed Ethernet Level Walk to Town Square and Russian River Beach TOT # 798N

4.9 out of 5 average rating, 118 reviews

Healdsburg 2br Cottage with Private Yard!

Relax at our renovated private guesthouse a 5 min drive (1 mi) from the Healdsburg Plaza. Updated 2 br/ 1 ba home with private yard and outdoor dining and lounge areas. Our layout is ideal for one family or friends traveling together as the one bathroom is accessed through the primary bedroom. Perfect for a wine country getaway- convenient location just outside of Healdsburg city limits in a vineyard adjacent neighborhood. We love kids and welcome them! Permit #TVR22-0119

4.96 out of 5 average rating, 116 reviews

Mediterranean Getaway with breakfast Healdsburg

An attractive, ultra-romantic, almost-a-cottage Bed&Breakfast is waiting for you in our restored 1930s-era home in a peaceful corner of northern Sonoma County. Ours is a quiet rural road nestled in beautiful oaks, redwoods, California bay, and buckeye trees near the bottom of Fitch Mountain, some 100’ above the Russian Rive. Fitch Mountain is known for its interesting local history, eclectic building styles, beautiful views, secluded neighborhoods, and friendly spirit.

5 out of 5 average rating, 166 reviews

10-Acre Vineyard Cottage w/Hot Tub + Bocce Court

Escape to a private and peaceful retreat surrounded by Russian River Valley Chardonnay and olive trees. Set on 10 acres of producing vines, our cottage offers vineyard views, a bocce court, fire pit, garden, cruiser bikes, and a sparkling hot tub. Immerse yourself in world-class food, wine, cycling, and nature. Guests staying 3+ nights will receive a complimentary bottle of Chardonnay crafted from our vines. Your perfect wine country escape awaits!

4.93 out of 5 average rating, 336 reviews

Healdsburg Cottage-Workspace, Walk to Plaza

This light-filled cottage is a comfortable, easy to access hide-away in a friendly, historic neighborhood just 5 blocks from the Healdsburg Plaza. Have a glass of wine or dine at your own picnic table in the private, garden setting. Relax in the adirondack chairs. Build a fire in the fire pit (weather permitting). It's an easy stroll into town for wine tasting, shopping or dinner. Transient Occupancy Tax (TOT) of 16% is included in the price.

4.97 out of 5 average rating, 586 reviews

Farm stay in Healdsburg

Gracianna Winery Vineyard Loft - Farm Stay

Costs vary based on availability. Luxury estate loft in Gracianna Winery's vineyard on Westside Road's Miracle Mile of Pinot Noir in Healdsburg includes equipped kitchen. Pick up breakfast needs before arriving. Vineyard machines may work overnight with lights & disruptive noises, especially during the summer and harvest is in late August early Sept. TASTING ROOM CLOSED DECEMBER 1 - MARCH 31. LOFT AVAILABLE YEAR ROUND. TOT #3294N

4.97 out of 5 average rating, 204 reviews

Healdsburg Contemporary Cottage With Lush Backyard Patio

Your private Healdsburg retreat—just a 4-minute walk to downtown wine tasting rooms, restaurants, shops, and the Farmers Market. This stylish guest cottage offers parking in front of a private entry, garden with al fresco dining, BBQ, lounge area, and a fully equipped Pilates studio. Designed with international contemporary art and thoughtful touches, it’s perfect for a weekend escape or a longer stay while house hunting.

4.99 out of 5 average rating, 280 reviews

Luxurious, Private, Healdsburg Guest Cottage

1083 Guest House is a Healdsburg find; comfortable luxury in a spacious private cottage with terrific amenities within walking distance of four-star restaurants, wineries, fabulous boutique shopping, and the Russian River. Your secluded cottage is nestled in the trees with views of a wooded area and is the perfect destination for your personal romantic getaway to enjoy all that the Wine Country has to offer.

5 out of 5 average rating, 196 reviews

Bee Haven Cottage

This unique property is located only 2.4 miles from Healdsburg Plaza. Situated on a historic 11-acre farm with 5 acres of Zinfandel grapes. This newly renovated Studio cottage was built in 1903. This creekside cottage is fully restored in an artist's handcrafted manner. All the furnishings are of the highest quality. Enjoy the natural surroundings while soaking in the private outdoor spa.

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Popular amenities for Healdsburg holiday rentals

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Other great holiday rentals in Healdsburg

4.98 out of 5 average rating, 82 reviews

Vineyard views, stunning house & deck

JohnRating, 5 stars3 weeks ago

This was our second stay with Julia. The home is very comfortable, clean and has mini-split heating and AC. We especially enjoy the country setting and views of the vineyards and hills of West Dry Creek from the large outside deck. The deck is perfect for the morning sun and partially shaded by the adjoining hill and oak trees in the afternoon. The property is just minutes to some of the best wineries in Dry Creek, and close to Geyserville, Alexander Valley and the upper end of the Russian River Valley. Big John's Market and Healdsburg are also less than ten minutes away.

5 out of 5 average rating, 30 reviews

Vineyard Oasis: Luxury Home in the Heart of Sonoma

Bei-ErRating, 5 stars1 week ago

Amazing location, with beautiful, serene views of the vineyards and very quiet with tons of privacy! We loved how spacious the home was, and Glenn was extremely responsive and gave wonderful recommendations for local wineries! We are so excited for our next trip back....thank you Glenn!!

5 out of 5 average rating, 58 reviews

Home in Geyserville

Spectacular views from hot tub

PiyushRating, 5 stars2 weeks ago

Absolutely loved our stay at Jill's place. Stunning views and a very unique AirBnB experience. Really enjoyed our stay. Jill was very responsive and prompt with help when we needed it. Definitely coming back again.

Place to stay in Sebastopol

5 out of 5 average rating, 92 reviews

The Sonoma Spyglass | Incredible Views + Sauna

RustyRating, 5 stars1 week ago

We loved our stay at Jade’s Spayglass! Such a lovely place and absolutely beautiful surrounding Sonoma County rural/farm country. Everything was as expected and better. We will be coming back!

5 out of 5 average rating, 93 reviews

Modern, Secluded Retreat - Walk to the Plaza!

JanRating, 5 stars2 weeks ago

This home and location are outstanding. The house was exactly as described and the setting was tranquil and relaxing. We loved the coffee station, crisp linens and fluffy towels. The house is very well maintained and Emily is very responsive. For this weekend it was just two of us but the place would easily accommodate 6.

5 out of 5 average rating, 32 reviews

Healdsburg Plaza Charmer w/ Hot Tub!

AngelaRating, 5 stars1 week ago

We stayed at the Clementine Cottage while in town for a wedding, and it was absolutely perfect. The home was cozy, charming, and thoughtfully appointed—everything we needed for a comfortable stay. The location was ideal for exploring Healdsburg, and coming back to the hot tub after a night of dancing was the ultimate treat! Highly recommend for anyone looking for a peaceful and well-located getaway.

4.97 out of 5 average rating, 38 reviews

Cabin in Cazadero

Caz Treehouse: Haven in the Redwoods

ChrisRating, 5 stars1 week ago

Heaven on Earth!!! This home nestled among the beautiful Redwood forest could not be more perfect. The kitchen has everything you could possibly need to prepare a gourmet dinner. The master bedroom is beautiful and the king bed is possibly the most comfortable we have ever slept in. Genevieve has thought of everything...each side of the bed has an iphone/apple watch charger and bed heater which made the already amazing bed even more cozy. We loved the heated toilet seat...might have to get one for our house now! The hot tub and infared sauna were perfect after a day exploring wine country. There is a lot to do in the surrounding area. Thank you for sharing your magical home with us. We will certainly be back!