
House vacation 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.

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! *Hot tub is inoperable from 10/26-11/1

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

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.

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

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.

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!

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

Modern mid-century-inspired, Deer Ranch

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

Wine Country Retreat- Privacy-Spa/Pool/Games

Modern wine country stunner!

Happy House Getaway - Pool, Hot Tub & Wine Country

Wine Country Opulent Villa-Brush Creek

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

Vineyard Retreat • Steps to Tastings • Press Pick
Weekly house rentals

Spectacular Vineyard View!! SPA, Close to Plaza!

Sonoma County Historical Ranch House on a Vineyard

Healdsburg House - Chiquita Road

Sebastopol Guest House

Sonoma VIEWS | Minutes to Dwtn | Couples/Families

Modern Wine Country Cottage

Rated Top 5% Modern Cozy Farmhouse in the Redwoods

Dillon Beach Nirvana
Private house rentals

Cuvée House

Modern Wine Country Escape - 10min to Healdsburg

Vineyard views, hot tub, sauna, cinema!

Spectacular views from hot tub

The Healdsburg Haven

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

Healdsburg Plaza Charmer w/ Hot Tub!

Epic Views! Wine Country Retreat: Sonoma County
When is the best time to visit Healdsburg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $441 CAD | $441 CAD | $500 CAD | $526 CAD | $567 CAD | $525 CAD | $586 CAD | $568 CAD | $600 CAD | $544 CAD | $544 CAD | $544 CAD |
| 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 vacation rentals
Explore 80 vacation rentals in Healdsburg

Nightly prices starting at
Healdsburg vacation rentals start at $70 CAD 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 and 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

Wifi availability
80 of Healdsburg vacation 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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