
House holiday rentals in Healdsburg
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Top-rated house rentals in Healdsburg
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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.

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.

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.

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

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

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.

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.

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

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.

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!

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!

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
House rentals with a pool

Woodhawk Manor of Alexander Valley

Modern mid-century-inspired, Deer Ranch

Sonoma Country Club Wine Country w/ pool

Modern wine country stunner!

PrivateWarm&Cozy+Spa+Pool+FirePit+Wifi!

Leo’s Lodge - Lux Retreat with Pool and Hot Tub

Vineyard Home • Steps to Tastings • Press Pick

Spectacular Sonoma: Views! Stars! Cielo.
Weekly house rentals

Heron House: Ocean View, Fully Remodeled

Sonoma County Historical Ranch House on a Vineyard

Healdsburg House - Chiquita Road

Olive House

Modern Wine Country Cottage

Dillon Beach Nirvana

Healdsburg Plaza Charmer w/ Hot Tub!

Zen House on 15 acres
Private house rentals

Healdsburg Wine Country Oasis, Hot Tub & Bocce

Cuvée House

Sonoma Retreat w/Pool, Hot Tub, Ent Barn + Orchard

Russian River Luxury Escape | Private Hot Tub

Spectacular views from hot tub

Serene Spa-Style Retreat with Fireplace & Hot Tub

Mill Creek - AvantStay | Patio, Hot Tub, A+ Design

Luxurious 3-Bedroom Home in Healdsburg
When is the best time to visit Healdsburg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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 |
| Avg. temp | 10°C | 10°C | 11°C | 11°C | 12°C | 13°C | 14°C | 14°C | 15°C | 13°C | 12°C | 10°C |
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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