
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.

Pool•Spa•6 Bikes•1mi to Town•Fire Pit•ShuffleBoard
This beautifully designed 3bd/2bth luxury home is bursting with resort-like amenities to ensure your stay is relaxing & fun. Comfortably sleeps 8, incl. a pull-out couch in a private bonus room - 1mi - Dwntwn Healdsburg & 20+ wineries. - Pool & Hot Tub - Lush 3/4 acre lot w/20+ orchard trees - 6 Adults Bikes - Shuffle Board, Outdoor Giant Chess & Jenga, Croquet, Ping Pong - Outdoor Dining, BBQ, Lounge Seating, Fire Pit - Pac N Play & High Chair - 3 Smart TV's -Netflix/Disney+ - Pet friendly

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.

Stylish Sonoma Oasis + Hot Tub - Near Wineries
Enjoy a stylish stay in wine country at this centrally located 3 bedroom retreat only 5 mins from Sonoma Plaza. Nestled on the desirable east side of town and surrounded by world-class wineries, including Gundlach Bundschu (the oldest family-owned winery in California) at the end of our tranquil street. Step outside to your private bucolic oasis with wraparound deck, seasonal creek and hot tub where you can unwind sipping local wine while dining al fresco underneath olive & citrus trees.

The Beach House
This stunning house sits on a bluff directly above the ocean. Sit in the living room with a 180 degree view of the ocean, hear the waves as they roll in, watch birds of prey land on a cypress tree, and deer, foxes and other wildlife forage on the hill. Occasionally, see a whale or dolphin swimming off shore. At dusk, watch the sun set as you make dinner in the fully equipped kitchen with all new appliances. Later watch the moon and stars come out as you relax to the sound of the waves.

Vineyard Vista, Modern Farmhouse Cottage with Pool
Our architect remodeled (2021), five star, elegant Farmhouse with great room and fireplace, is simply perfect throughout. This unique wine country two-acre property, with heated swimming pool (for a fee), looks out to the beautiful Russian River vineyards and the never-ending Western panorama. Only minutes from award winning food and shopping in downtown Healdsburg, it’s within easy walking or bicycling distance of tasting rooms at J, Rodney Strong and other acclaimed Sonoma wineries.

Ocean Front Paradise w Hot Tub&Fire Pit
Welcome to Cliff House! Nestled on the stunning Northern CA coast, this home has unparalleled ocean views. Enjoy a 10 minute walk to Duncan's Cove or Wright's Beach. From the impressive waves and tide pools in the winter months to the warm ocean breezes in the summer sun, it's always a great time to visit.- Luxe bedding, fully equipped European size kitchen, hot tub & fire pit- Come to escape or do it all! Wine Country (45mins) Northwood Golf Course (20mins) Kayaking in Jenner (10mins)

A sophisticated Wine Country Cottage with Hot tub
Thornsberry Cottage is a luxe Country Cottage just 5 minutes from the Sonoma Square. Featuring two separate buildings, with a bed and bath in each, it is renovated with a boutique hotel feel to accommodate the most discerning traveler. Located on the east side town it is in short distance to the 2 oldest wineries in California. The home offers a true escape where one can spin a record by the fire pit, relax in the hot tub, or walk or bike to Gundlach Bundschu at the end of our road.

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.

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

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!
Popular amenities for Healdsburg house rentals
House rentals with a pool

Modern mid-century-inspired, Deer Ranch

Wine Country Retreat- Privacy-Spa/Pool/Games

Modern wine country stunner!

Serene Wine Country Retreat with Pool & Hot Tub

Luxury home (+ pool house) with views, pool & spa

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

Happy House Getaway - Pool, Hot Tub & Wine Country

Sonoma 14Acres, 2BR 2BA, Pool HotTub, Plaza 3 mi.
Weekly house rentals

Luxurious Healdsburg Home Walk to Wineries

Spectacular Vineyard View!! SPA, Close to Plaza!

Sonoma County Historical Ranch House on a Vineyard

Healdsburg House - Chiquita Road

Quiet Wine County Retreat with Bocce and Hot tub!

Modern Wine Country Cottage

Holiday Healdsburg Plaza Charmer w/ Hot Tub!

Zen House on 15 acres
Private house rentals

Cuvée House

Luxury Villa, Pool, Spa, BBQ, By Healdsburg

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

Vineyard Oasis: Luxury Home in the Heart of Sonoma

Sonoma Creek Haven – Creekside Near 20+ Wineries

Luxury Spa Retreat: Fireplace, Hot Tub & Garden

Best View Wine Country Oasis: Pool-Hot tub-Sauna

Meadowhouse | Secluded Sonoma Wine Country Retreat
When is the best time to visit Healdsburg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $542 NZD | $542 NZD | $615 NZD | $647 NZD | $697 NZD | $646 NZD | $738 NZD | $604 NZD | $664 NZD | $713 NZD | $670 NZD | $670 NZD |
| 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 $86 NZD 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 and kid-friendly amenities

Pet-friendly accommodation
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

Wi-Fi availability
80 of Healdsburg holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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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