
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.

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

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

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!

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.

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.

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.

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
House rentals with a pool

Modern mid-century-inspired, Deer Ranch

Vineyard House Pool Hot Tub by Inspired in Sonoma

Modern wine country stunner!

Serene Wine Country Retreat with Pool & Hot Tub

Wine Country Opulent Villa-Brush Creek

Happy House Getaway - Pool, Hot Tub & Wine Country

Vineyard Retreat • Steps to Tastings • Press Pick

Naidu Vineyards - Views/Pool/Spa/Bocce/9 Acres
Weekly house rentals

Pelican Hill House

Birdwatching in Bodega Bay

The Beach House

Healdsburg House - Chiquita Road

Dreamy A-Frame Luxury - Privacy - Views-Hot Tub

The Healdsburg Haven

Modern Wine Country Cottage

Gorgeous Victorian in the HEART of Windsor
Private house rentals

Cuvée House

Vineyard views, stunning house & deck

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

Vineyard Oasis: Luxury Home in the Heart of Sonoma

Spectacular views from hot tub

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

Healdsburg Downtown 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 | ﺩ.ﺇ1,157 | ﺩ.ﺇ1,157 | ﺩ.ﺇ1,311 | ﺩ.ﺇ1,381 | ﺩ.ﺇ1,487 | ﺩ.ﺇ1,377 | ﺩ.ﺇ1,539 | ﺩ.ﺇ1,491 | ﺩ.ﺇ1,576 | ﺩ.ﺇ1,429 | ﺩ.ﺇ1,429 | ﺩ.ﺇ1,429 |
| 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 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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