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Holiday rentals in Healdsburg

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Quick stats about holiday rentals in Healdsburg

  • Total holiday rentals

    Explore 140 holiday rentals in Healdsburg

  • Nightly prices starting at

    Healdsburg holiday rentals start at €43 per night before taxes and fees

  • Verified guest reviews

    Over 7,860 verified reviews to help you choose

  • Family-friendly holiday rentals

    90 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wifi availability

    140 of Healdsburg holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Healdsburg rentals

  • 4.9 Average rating

    Healdsburg stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated holiday rentals in Healdsburg

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

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Top guest favourite
An airy living space is highlighted by high-beamed ceilings and large windows, allowing plenty of natural light. A gray sofa and two brown leather chairs are arranged around a round coffee table on a light-colored rug. The adjacent dining area features a wooden table, surrounded by various chairs.
Home in Healdsburg

Healdsburg House - Chiquita Road

Relax with the whole family at this peaceful and private home mins to the Healdsburg Square, Montage Resort, and Dry Creek/Alexander Valley Wineries. The updated home features an open concept kitchen, two family rooms, and a sparkling hot tub on 1.5 private acres surrounded by vineyards and oak trees. Cruise your bike to town or head directly out Chiquita Road to some of the world's greatest cycling. 2.4 miles to the Montage Resort. 2.5 miles to the Healdsburg Square. Welcome to Wine Country!

5.0 out of 5 average rating, 123 reviews
Superhost
An aerial view reveals a spacious property surrounded by lush vineyards. The main house is situated to the left, with a sparkling pool adjacent to it. A winding road leads through the greenery, while gentle hills stretch into the distance under a clear blue sky.
Home in Healdsburg

Dry Creek Ranch ~ (Tariff Discount) Hot Tub & Pool

Enjoy an idyllic wine tasting weekend for 3-4 couples, have fun with the whole family (pets welcome) or find adventure along the world famous Dry Creek Road. This property boasts a main house, pool house & Game barn. The main house sleeps 10. The pool house features a 70” flatscreen, a Live Edge tasting bar and Lanai. The property is only 1.4 miles from Healdsburg’s square. Take a gentle bike ride into town or stay put – pour wine, soak in the hot tub, and watch the sun set over the vineyards

4.9 out of 5 average rating, 107 reviews
Guest favourite
A modern living area showcases a comfortable gray sectional sofa and two accent chairs. A round wooden coffee table sits in the center, with a small plant adding a touch of greenery. Soft lighting is provided by a ceiling fixture and table lamps, enhancing the inviting atmosphere.
Home in Healdsburg

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 close 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

4.92 out of 5 average rating, 155 reviews
Top guest favourite
The exterior showcases a landscaped garden featuring diverse greenery, decorative rocks, and a serene stone pathway. A gazebo is positioned in the garden, complementing the house’s two stories, which are framed by trees and plants. The scene is illuminated by soft natural light.
Home in Santa Rosa

Elegant & Spacious Luxury Wine Country Estate

The perfect place for your group to stay in Wine Country! Featuring two large entertaining areas and an additional dining room, this is a great place for fun and relaxation! Play ping pong, pool or poker in our game room, or dine on our spacious patio under the pergola! Relax and soak in our hot tub and enjoy the zen gardens and tranquil water feature, or sip on a glass of wine by the outdoor fire pit. Close to the Sonoma County Airport, wineries, and world-class dining. Welcome home!

4.97 out of 5 average rating, 241 reviews
Top guest favourite
Home in Healdsburg

Modern Healdsburg Retreat • Hot Tub, Bocce & Views

Vineyard views + hot tub under the stars—modern Healdsburg, 5 min to the Plaza. Set in Dry Creek Valley, this design-forward retreat feels a world away—yet you’re minutes from top wineries, tasting rooms, and dining. Slow mornings with coffee overlooking the vines. Golden-hour dinners outside. Evenings in the hot tub with sunset views and total privacy. Designed for relaxed Wine Country living with bocce, outdoor lounge spaces, and seamless indoor-outdoor flow.

4.93 out of 5 average rating, 179 reviews
Top guest favourite
Cottage in Geyserville

Country Carriage House in Downtown Geyserville

Linger over coffee on your quaint patio amongst 6 acres downtown in sweet Geyserville. An industrial loft vibe with wine country bones—the cottage is modern/rustic meets country-correct. Immerse yourself in country life or walk to downtown Geyserville for an Aperol Spritz. Truly where design meets refuge. Goats, horses, dogs, one heifer 🐄 named Francis, and one farm cat named Leo on property. Fully fenced front yard and back patio!

4.99 out of 5 average rating, 181 reviews
Top guest favourite
Home in Healdsburg

Healdsburg Garden House

Hidden gem Best Value Ideal space for reunions and bridal parties (no events) Clean, Cozy & Private House Near Healdsburg Town Square. 20% discount for self serve rental Healdsburg Kayak Company Discount code - HEALDSBURGGARDEN20 Centrally located for Sonoma county day trips… Covered redwood deck with gas grill 50” HDTVs and fast 1 GB Wi-Fi. Fully stocked kitchen w/ dishwasher. New A/C and heating. TOT #798N

4.93 out of 5 average rating, 655 reviews
Top guest favourite
A spacious outdoor deck is furnished with a large sectional sofa and several lounge chairs, all adorned with blue cushions. A wooden coffee table sits in the center, surrounded by lush greenery and trees, creating a serene and private atmosphere.
Guest house in Healdsburg

Luxurious, Private, Healdsburg Guest Cottage

1083 Guest House is comfortable luxury in a spacious private cottage 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 base for your Wine Country get away. There is no stove/oven due to zoning/licensing so the cottage has a microwave, small air fryer, toaster and bbq.

4.99 out of 5 average rating, 321 reviews
Guest favourite
A bright living area features a spacious white sectional couch and a wooden coffee table. An expansive bookshelf holds various items, with a television and fireplace being focal points. Large glass doors open to a garden, bringing in natural light and outdoor views.
Guest house in Healdsburg

Designer Cottage | Garden Oasis | Walk to Plaza

✓ Fully equipped kitchen. ✓ On-site EV charger. ✓ Lush, private garden. ✓ Dedicated workspace. ✓ Just a 4-minute walk to Healdsburg Plaza. ✓ Stylish retreat created especially for couples. ✓ Close to world-class wineries and dining. ✓ Comfortably accommodates 2 guests. ✓ Seamless indoor-outdoor living. ✓ Private, architect-designed cottage for two. ✓ Comfortable Queen Bed with Hotel pressed Sheets.

4.97 out of 5 average rating, 256 reviews
Guest favourite
A modern living room features two comfortable armchairs and a sleek sofa, complemented by a coffee table adorned with a globe. A flat-screen TV is mounted on the wall, and natural light fills the space through large windows. An inviting atmosphere is created by neutral tones.
Holiday home in Healdsburg

Downtown Healdsburg Nest

You can't get any closer to all that Healdsburg has to offer. Just two blocks from the charming Plaza, this fully furnished, upstairs 2 bdr apartment has everything you need for a quick trip to Wine Country or longer-term stay. High-speed internet and all the comforts of home. Steps away from world-class restaurants, tasting rooms, shops, galleries, and music venues.

4.96 out of 5 average rating, 112 reviews
Top guest favourite
A hot tub is positioned on a grassy area, offering a view of rows of grapevines against a serene sunset. Colorful flowers are visible nearby, complementing the natural surroundings.
Home in Healdsburg

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. Your perfect wine country escape awaits!

5.0 out of 5 average rating, 268 reviews
Top guest favourite
The exterior of a charming cottage is framed by lush greenery and features a welcoming entrance with wooden doors. A stone pathway leads to the home, which is complemented by vibrant foliage and a pergola adorned with vines.
Home in Healdsburg

Dry Creek Valley Cottage

We live in a beautiful rural country setting but we are only a 5-7 minute easy drive into downtown Healdsburg where all the lovely shops, wineries and restaurants are. We invite you to enjoy our lovely garden and taste all the wonderful fruit when it is in season. We have apple, pear, peach, plum, pomegranate, persimmon and citrus trees.

4.96 out of 5 average rating, 494 reviews

Popular amenities for Healdsburg holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Healdsburg's top sights

Healdsburg Plaza

85 locals recommend

J Vineyards & Winery

62 locals recommend

Big John's Market

53 locals recommend

Jordan Vineyard & Winery

34 locals recommend

Duke's Spirited Cocktails

33 locals recommend

Rodney Strong Vineyards

32 locals recommend

Other great holiday rentals in Healdsburg

Guest favourite
A pathway leads to a welcoming front porch, flanked by greenery and blooming flowers. The light-colored home is partially shaded by surrounding trees, creating a serene approach. The yard features fresh landscaping with mulch and various plants, enhancing the inviting entrance.
Home in Healdsburg

Peaceful location, hot tub, fire pit, game room!

4.88 out of 5 average rating, 363 reviews
Top guest favourite
The exterior of a rustic winery building is featured, characterized by its earthy tones and distinctive red door accents. Lush greenery and blooming purple flowers surround the structure, enhancing its natural setting. The building's design includes terracotta roofing and large windows that invite an abundance of natural light.
Farm stay in Healdsburg

Gracianna Winery Vineyard Loft - Farm Stay

4.97 out of 5 average rating, 707 reviews
Top guest favourite
A spacious outdoor patio is depicted, featuring comfortable seating arranged around a decorative table. A hot tub is visible nearby, accompanied by landscaped areas. A large umbrella provides shade while scenic vineyard views stretch into the distance.
Home in Healdsburg

Luxe Healdsburg 3BR Home + Comp Ridge Wine Tasting

5.0 out of 5 average rating, 76 reviews
Top guest favourite
Home in Healdsburg

The Grove on Alexander Valley

5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Healdsburg

ALBA | A modern luxury retreat in Healdsburg

4.97 out of 5 average rating, 29 reviews
Top guest favourite
A living area features a green upholstered sofa and patterned accent chairs. A round coffee table sits at its center, adorned with fresh flowers. Light streams in from large windows, highlighting the area rug beneath, while a dining space is visible through the open doorway.
Home in Healdsburg

Cuvée House

5.0 out of 5 average rating, 53 reviews
Top guest favourite
Home in Healdsburg

Vineyard View Retreat • Fire Pit • Wine Perks

4.96 out of 5 average rating, 98 reviews
Top guest favourite
Home in Healdsburg

Healdsburg Plaza Pet-Friendly Charmer + Hot Tub

4.99 out of 5 average rating, 75 reviews

When is the best time to visit Healdsburg?

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Avg. price€287€286€287€315€324€319€375€361€359€311€315€292
Avg. temp10°C10°C11°C11°C12°C13°C14°C14°C15°C13°C12°C10°C

Frequently Asked Questions

  • What are the best places to stay in Healdsburg?

    Healdsburg has charming stays around its historic plaza, tree-lined neighborhoods, and vineyard-dotted countryside. Many travelers enjoy accommodations that blend locally rooted character with walkable access to shops, tasting rooms, and restaurants.

  • What are the best things to do in Healdsburg with kids?

    Many families explore parks, discover exhibits at local museums, and enjoy picnics around the plaza. Outdoor enthusiasts often visit the Russian River for nature activities, or explore nearby hiking and wildlife viewing opportunities.

  • What are some of the best things to do in Healdsburg?

    Healdsburg has tasting rooms, locally-owned shops, and a lively plaza at its heart. Many guests stroll the farmers market, explore galleries, or join tours at nearby wineries and vineyards.

  • How is the weather in Healdsburg?

    Healdsburg has mild winters around 45–56°F (7–13°C) with more rain, and drier, warmer summers near 51–66°F (11–19°C). Spring and fall often bring comfortable transitions with fewer showers and pleasant temperatures.

  • When is the best time to visit Healdsburg?

    Late spring through early fall is frequently suggested for warmer weather, events, and outdoor activities. In autumn, grape harvest season brings vivid vineyard colors and a festive atmosphere around town.

  • What are the best places to visit in Healdsburg?

    Visitors often explore Healdsburg Plaza, visit nearby wineries and tasting rooms, and stroll through local art galleries. The Russian River area draws those seeking nature and scenic views.

  • What are some hiking trails in Healdsburg?

    Explore trails at Healdsburg Ridge Open Space Preserve for oak woodlands and panoramic vistas. Local parks around the Russian River and Fitch Mountain also have scenic routes for walkers and hikers.

  • What are some family activities we can do in Healdsburg?

    Families often picnic in the plaza, explore playgrounds, and visit local museums focused on regional history. Kayaking or canoeing on the Russian River is also frequently suggested as a way to connect with nature.

  • What are some of the best day trip ideas from Healdsburg?

    Consider exploring the redwoods, coastal beaches, and neighboring small towns—each has its own unique character and locally rooted attractions. Wine enthusiasts may appreciate scenic vineyard drives, while outdoor adventurers can seek regional parks and river activities.

  • Are there any pet friendly accommodations available in Healdsburg?

    Many accommodations in Healdsburg welcome pets, especially in neighborhoods near the downtown plaza or around quieter, residential areas. Parks and nearby trails make it easy to spend time outdoors with dogs.

  • What are some local tips for visiting Healdsburg?

    Locals suggest packing layers, as mornings and evenings can be cool even in summer. Early reservations for tastings and restaurants are often recommended, and many enjoy the area’s Saturday farmers market for regional produce and baked goods.

  • What is Healdsburg known for?

    Healdsburg is known for its vibrant wine culture, locally owned restaurants and shops, and the welcoming plaza at the heart of town. The area’s wineries, scenic river, and agricultural traditions shape much of its character.

  • What are the best hidden gems to explore in Healdsburg?

    Travelers enjoy discovering smaller family-run wineries, tucked-away art studios, and hiking trails in the Healdsburg Ridge Open Space Preserve. Farmers markets and cafes off the main square often provide a more local perspective.

  • What are the best foods to try in Healdsburg?

    Healdsburg’s food scene often highlights Sonoma County produce, artisan cheeses, and local olive oils. Seasonal dishes at farm-to-table restaurants, traditional pastries, and regional wines are frequently suggested.

  • What should I bring for a trip to Healdsburg?

    Pack comfortable walking shoes, layers for changing temperatures, and a light rain jacket for winter or spring visits. A reusable water bottle and sun protection are also helpful for exploring outdoor spaces.

  • What is the nightlife in Healdsburg like?

    Nightlife in Healdsburg centers on relaxed wine bars, live music in local venues, and friendly tasting rooms. Many enjoy after-dinner strolls around the plaza or gathering at outdoor patios.

  • What are the most popular events or festivals in Healdsburg?

    Healdsburg hosts wine harvest celebrations in autumn, a lively farmers market season in warmer months, and recurring art, food, and music festivals throughout the year. Events around the plaza are a vibrant part of the community calendar.

  • Are there family friendly vacation rentals in Healdsburg?

    Healdsburg has many family-friendly vacation rentals, especially near parks or in quiet, residential neighborhoods. Spacious homes and cottages with outdoor areas are frequently suggested by guests traveling with children.

Destinations to explore