House holiday rentals in Healdsburg

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Top-rated house rentals in Healdsburg

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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
4.96 out of 5 average rating, 479 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.

Top guest favourite
A warm living space features wooden paneling and natural light from large windows. A comfortable chair sits beside a small wooden table, and a piano is positioned nearby. Decorative plants hang from the ceiling, complemented by a cozy fireplace and a bookshelf in the background.
Home in Forestville
4.96 out of 5 average rating, 294 reviews

Forest Cozy Home

My house in Forestville is a walk to the river (Steelhead County Beach), near endless wineries, canoe rentals, gorgeous Sonoma coast beaches, Santa Rosa airport, a bicycle trail through West County with bike rentals in downtown Forestville offering immediate access to the trail, and a very well-stocked little grocery store a 5-minute walk down the hill. Lovely back roads take you to Healdsburg to the north or Sebastopol to the south. My dog & I stay in a basement studio when guests are here.

Guest favourite
The exterior of the cabin is nestled among tall redwood trees, featuring a multi-tiered structure with a large front deck. Stairs lead up to the entrance, with potted plants on the deck and a gravel path framed by lush greenery.
Home in Rio Nido
4.9 out of 5 average rating, 154 reviews

Raven Haven: Cozy Forest Storybook Cabin w Hot Tub

Nestled among majestic redwoods in the historic Rio Nido hamlet near Guerneville, Raven Haus is a delightful Hansel and Gretel cottage. Surrounded by towering firs, the whimsical charm of this cottage captures the essence of a bygone era. Located just a mile from the renowned Korbel vineyards and tasting room, guests can explore the local wine scene. The proximity to the popular Rio Nido Lodge and Roadhouse offers convenient options for dining, drinks, and entertainment within walking distance.

Guest favourite
A vibrant pink door welcomes guests to the home, framed by a green exterior and wooden porch. A wooden bench sits on the porch beside a decorative rooster. Lush greenery accents the area, providing a serene entryway.
Home in Forestville
4.96 out of 5 average rating, 169 reviews

Hilltop Haven 🌅 view & hot tub

Relax with the whole family at this peaceful place to stay on a quiet hilltop. This is a quaint 2 bedroom, 1 bath with a queen bed in one bedroom and bunk (twin over full) in the second bedroom. Relax in the hot tub or in the hammock on the backyard deck with a peaceful nature view or hang inside the cozy abode and make use of the fully-stocked kitchen. we have a limit of 4 overnight guests and 2 vehicles per Sonoma County permit rules. For more pictures on IG @hilltop_haven_vacation

Top guest favourite
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, 679 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 favourite
An expansive outdoor patio area features modern metal furniture and a covered dining table, inviting al fresco meals. Large sliding glass doors create a seamless flow between indoor and outdoor spaces, with a view of the surrounding natural landscape and vineyard beyond.
Home in Santa Rosa
4.97 out of 5 average rating, 128 reviews

WineCamp - Russian River Valley AVA - No Pets

The WineCamp concept is rooted in the rural ambience of working local vineyards and craft breweries. This purpose-built residence offers indoor/outdoor living at it best. Conceived as the ideal space for two adult couples, the spacious dual master suites are separated by gracious open-plan living areas that flow seamlessly through multi-panel sliding walls of glass onto the covered terrace and vineyards beyond. This wine and beer themed property is not suitable for children.

Top guest favourite
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, 279 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 favourite
Home in Healdsburg
4.93 out of 5 average rating, 150 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 favourite
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, 432 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 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
5 out of 5 average rating, 204 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 favourite
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, 141 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!

Top guest favourite
Home in Jenner
4.99 out of 5 average rating, 136 reviews

Jenner Gem: gorgeous retreat by the river

Feel the cool ocean breeze while admiring the views to the Russian River estuary. Kick back and relax in a peaceful and stylish setting. Grab your favorite drink and enjoy the beauty of the California coast. Just steps away from Pacific Highway 1 and walking distance to the river or a short drive to Goat Rock beach. Plus, you're just a short stroll down Aquatica Café. ***Please Read the Full Listing Description Before Booking***

Popular amenities for house rentals in Healdsburg

When is the best time to visit Healdsburg?

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Avg. price$408 SGD$408 SGD$463 SGD$487 SGD$525 SGD$486 SGD$556 SGD$455 SGD$500 SGD$537 SGD$504 SGD$504 SGD
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Quick stats about house rentals in Healdsburg

  • Total holiday rentals

    Explore 80 holiday rentals in Healdsburg

  • Nightly prices starting at

    Healdsburg holiday rentals start at $65 SGD per night before taxes and fees

  • Verified guest reviews

    Over 4,110 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    80 of Healdsburg holiday rentals include wifi 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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