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House vacation rentals in Healdsburg

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Top-rated house rentals in Healdsburg

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Top guest favorite
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
4.96 out of 5 average rating, 475 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.

Guest favorite
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
4.91 out of 5 average rating, 130 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 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

Top guest favorite
A private backyard features a solar heated swimming pool surrounded by lounge seating and potted plants. A tiki bar is visible in the background, with palm trees providing shade in the sunlight. The space combines relaxation and outdoor living for a serene atmosphere.
Home in Graton
5 out of 5 average rating, 675 reviews

Eco Luxury Private Sanctuary / The Farmhouse Oasis

**Very Important** Please read description below and “Other things to note” at the bottom of this section before contacting us. • Adults Only • Private Sunny 1 Bedroom, 2 full bathroom 900 sq ft stand alone home • Private Backyard with Pool, Sauna, Outdoor Shower, and Outdoor Bathtub • Luxurious Modern Farmhouse Style • Created to feel like a boutique hotel experience • In the heart of wine country Sebastopol/ West Sonoma • Eco-Friendly products used • Strict cleaning protocols

Top guest favorite
The ranch-style home is surrounded by landscaped gardens, featuring a driveway that curves gently towards the entrance. The exterior showcases a combination of light-colored siding and brick accents, with large windows allowing natural light to fill the interior spaces.
Home in Healdsburg
4.93 out of 5 average rating, 274 reviews

The Wine Ranch

The Wine Ranch Just five minutes north of Healdsburg Plaza, The Wine Ranch is a beautifully remodeled ranch-style home, set on over a half acre of lush outdoor space. The property features a bocce ball court, ping-pong, an expansive deck and patio perfect for al fresco dining or tranquil relaxation. Designed to host gatherings, the spacious living room, dining area, and gourmet kitchen create an inviting atmosphere for couples, families, or groups of up to eight friends.

Top guest favorite
Home in Healdsburg
4.92 out of 5 average rating, 146 reviews

Dry Creek Retreat- Bocce, Hot Tub, EV Charger

Ideally located 5 minutes from the Healdsburg Square on Dry Creek Road, this home is the perfect place for restoration or play! The modern home boasts spectacular vineyard views on a magical 1/2 acre lot, a hot tub, Bocce ball court, large deck, and a fully stocked kitchen. World class food, wine, cycling, and nature are at your fingertips here! -5 minutes to the Healdsburg Square with restaurants, tasting rooms, and shopping -10 minutes to dozens of wineries

Top guest favorite
A spacious living area features a blue sofa adorned with a soft orange throw. A large area rug with intricate patterns anchors the space, while natural light floods in through large windows. A wooden coffee table rests centrally, complemented by decorative items.
Home in Windsor
4.96 out of 5 average rating, 428 reviews

Winelight Vineyard Home With Spa

Gated driveway, private, scenic, safe, secure, and impeccably clean. Unwind, prepare dinner on granite counter tops in this newly remodeled well-stocked gourmet kitchen. Enjoy plush amenities, fine decor, hot tub, romantic fireplace, French doors leading to outdoor decks, secluded rural vibe, reliably fast internet. Close to Sonoma County's best wineries, breweries and restaurants. There is a guest laundry, designer carport, and ample parking for guests.

Top guest favorite
A charming single-story cottage is framed by vibrant plants, showcasing a well-kept lawn. Large windows invite natural light, while a welcoming front door is visible. The surrounding garden features colorful flowers, enhancing the tranquil setting.
Home in Healdsburg
5 out of 5 average rating, 198 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!

Guest favorite
Two modern, white structures stand beneath a large green tree against a clear blue sky. The buildings feature large glass windows, allowing for natural light. The area is surrounded by open grass, contributing to a relaxed and spacious atmosphere.
Home in Healdsburg
4.84 out of 5 average rating, 136 reviews

Three-Building Healdsburg Homestead with Wine Barn

Your Healdsburg Homestead for launching wine country adventure! Recently remodeled, 3 buildings on 1/2 acre, including a barn with a winetasting bar & game room! Great for families and groups. Perfectly located for cycling on the legendary Eastside/Westside loop. For wine lovers, we are across the street from Rodney Strong Vineyard and the amazing sparkling wines of the beautiful J Vineyard. Best of all, Healdsburg Plaza is just a short hop away!

Guest favorite
An open living space seamlessly connects with an outdoor deck, featuring a dining table set for several. Natural light floods the area, highlighting wooden flooring and a cozy rug. Lush greenery can be seen in the garden area beyond the deck, creating a serene atmosphere.
Home in Healdsburg
4.94 out of 5 average rating, 185 reviews

Wine Country Cottage Walkable to River or Downtown

Centrally located retreat 5 blocks from downtown, Russian River and 3 blocks from at least 9 wineries. Living room fully opens to private deck w/BBQ, outdoor kitchen, dining space and fire place. Gourmet equipped kitchen with many cooking amenities to enjoy wine and a great meal in the garden patio or BBQ outside and relax. Luxury bathroom with heated towel rack and bidet. A small cozy two bedroom with many amenities and thoughtful touches.

Top guest favorite
A warm living area is furnished with comfortable seating arrangements, including both a sofa and accent chairs. Natural wood paneling complements the cozy atmosphere. A collection of framed artwork adorns the walls, and a window offers a view of the outdoors. Several decorative items are placed on the coffee table.
Home in Guerneville
4.97 out of 5 average rating, 600 reviews

Relaxing "Hillside Lodge" Sleeps 4

Hillside Lodge is a tranquil oasis nestled on a hillside in the Russian River Valley. Spacious two-bedroom home has brand new luxury queen size beds. Fully-equipped modern kitchen. Wi-Fi. Front deck has view to wooded hills. Large, secluded back patio off bedrooms has lounge chairs and a hammock. Close to Stumptown Brewery. Distance to downtown is just under 1 mile.

Guest favorite
Home in Healdsburg
4.95 out of 5 average rating, 127 reviews

Beautiful, Spacious, ArtHaus!

Welcome to ArtHaus! 3 Bed, 3 Bath on 1.5 Acres. Super spacious living room opening onto an outdoor deck. Modern and fully equipped kitchen w/ glass and dining ware so you can stylishly host an entire dinner party. Home feature beautiful art pieces created by the homes designer Sargam Griffin. Completely separate guest house included.

Top guest favorite
A bright yellow exterior is complemented by vibrant flowers in front of the window. Lush greenery surrounds the area, highlighting a tranquil outdoor space. The view includes trees and open fields, suggesting a peaceful and natural setting.
Home in Healdsburg
4.93 out of 5 average rating, 620 reviews

Healdsburg Garden House

Recently redecorated house Sonoma style Central jump off point for all of Sonoma Super clean and sanitized Covered Redwood Deck with Gas Grill Proper A/C and Heating Private Fully Stocked Kitchen w/ Dishwasher 50” HDTVs 1 GB High Speed Ethernet Level Walk to Town Square and Russian River Beach TOT # 798N

Popular amenities for Healdsburg house rentals

When is the best time to visit Healdsburg?

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Avg. priceﺩ.ﺇ1,157ﺩ.ﺇ1,157ﺩ.ﺇ1,311ﺩ.ﺇ1,381ﺩ.ﺇ1,487ﺩ.ﺇ1,377ﺩ.ﺇ1,539ﺩ.ﺇ1,491ﺩ.ﺇ1,576ﺩ.ﺇ1,429ﺩ.ﺇ1,429ﺩ.ﺇ1,429
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Quick stats about house rentals in Healdsburg

  • Total vacation rentals

    Explore 80 vacation rentals in Healdsburg

  • Nightly prices starting at

    Healdsburg vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

  • Verified guest reviews

    Over 4,110 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Healdsburg vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Healdsburg rentals

  • 4.9 Average rating

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

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