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House holiday rentals in Windsor

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Top-rated house rentals in Windsor

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Home in Windsor

4.87 out of 5 average rating, 120 reviews

Charming Windsor Home

** This home is professionally managed by LegacyRnR. Let LegacyRnR handle your entire Wine Country get away weekend. We offer our own 11 passenger wine tasting tour van, as well as a 6 passenger Cadillac Escalade available to book. The rate for each vehicle is $100/hour with a 5 hour minimum. This rate includes all taxes and fees. It does not include gratuity for the driver. We can also pre stock the kitchen/pantry before you arrive. When you book with LegacyRnR, you can book your entire vacatio

Guest favourite

Home in Windsor

4.99 out of 5 average rating, 112 reviews

Gorgeous Victorian in the HEART of Windsor

Gorgeous renovated Queen Anne Victorian located in the heart of Windsor, CA combines quality finishes, modern convenience & vintage details. With a stylish kitchen, high ceilings, 3 beds/2 baths on a single level, HVAC & a huge lot with a Bocce Court. Walking distance to the Town Green, restaurants, wine tasting rooms and shopping. Just 3.5 miles from the Sonoma County Airport (STS), 5 miles to downtown Healdsburg, in the heart of the Russian River Valley & just 57 miles from the Golden Gate.

Guest favourite

Home in Forestville

4.96 out of 5 average rating, 262 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

Home in Windsor

4.96 out of 5 average rating, 140 reviews

Spacious, Modern, Convenient Wine Country Home

Welcome to our luxurious, modern, and spacious, wine country home! Conveniently located, this home is walking distance to one of Sonoma County's best golf courses, just a 12 min drive to downtown Healdsburg, 4 min drive to downtown Windsor, 7 min drive to Santa Rosa airport. Surrounded by wineries, breweries and world-class dining. This home features plenty of room to sleep a large group of guests, ping pong table, outdoor fire pit, BBQ and covered outdoor dining. Relax and enjoy your stay.

Guest favourite

Home in Windsor

4.96 out of 5 average rating, 397 reviews

Winelight Vineyard Home With Spa

Available for minimum 3 day rental. 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.

Guest favourite

Home in Healdsburg

4.93 out of 5 average rating, 562 reviews

Healdsburg Garden House

Enjoy a real Sonoma County Experience Best Value in the Valley Organic grapes, hops, flower and vegetable gardens Centrally located home away from home Large Covered Redwood Deck with Gas Grill NEW A/C and Heating (controls in each bedroom) Super clean and sanitized Private, spacious & comfortable Fully Stocked Kitchen w/ Dishwasher 50” HDTV’s in each room (HBO, Showtime, Netflix, YouTube…) 1 GB High Speed Ethernet Level Walk to Town Square and Russian River Beach TOT # 798N

Guest favourite

Home in Graton

5 out of 5 average rating, 606 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 covid cleaning protocols

Guest favourite

Home in Santa Rosa

4.94 out of 5 average rating, 190 reviews

Winemaker's Delight: 3BD/3BA Russian River Valley

Welcome to Wine Country Haven, a splendid 3-bedroom retreat nestled in the heart of Santa Rosa, owned by passionate wine makers. While not on a vineyard, this cozy abode is designed to immerse you in the spirit of viticulture, offering a unique and charming getaway for wine enthusiasts and those seeking a taste of the good life. Indulge in the warmth and comfort of our wine-inspired home. This retreat is perfect for up to six guests, whether you're traveling with friends or family.

Guest favourite

Home in Santa Rosa

4.96 out of 5 average rating, 108 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.

Guest favourite

Home in Healdsburg

5 out of 5 average rating, 127 reviews

10-Acre Vineyard Cottage w/Hot Tub + Bocce Court

Relax at this private and peaceful home surrounded by mature Russian River Valley Chardonnay and olive trees. Featuring spectacular vineyard views, a bocce ball court, fire-pit, garden, cruiser bicycles, and a sparkling hot tub on 10 private acres of producing vines. Be immersed in world class food, wine, cycling, and nature at our cottage. Guests staying 3 nights or more will enjoy a complimentary bottle of Chardonnay produced from our fruit.

Home in Healdsburg

4.79 out of 5 average rating, 459 reviews

C - Wineries/breweries seconds away

Great location for a wine country getaway! Please use the Airbnb app for self check-in instructions! The owner is severely allergic to animals, so please do not request or bring any animal with you. We have an automated backup generator for loss of power issues! Full kitchen, Outdoor patio, BBQ, Fire pit (propane tank included but not fuel), Two bikes included in stay. California King Tempurpedic bed. Laundry room, Fully renovated bathroom.

Guest favourite

Home in Windsor

4.93 out of 5 average rating, 158 reviews

Luxurious home and pool

Beautiful executive home loaded with sophisticated upgrades. This spacious open floor plan features 4 bedrooms, 3 baths, and a private pool with a fountain. The gourmet kitchen, hardwood floors, and granite counters are all part of the great room with fireplace. Centrally located in Sonoma county with more than 20 wineries within a 10 minute drive. This house is just 5 miles from Healdsburg and 20 miles from Calistoga.

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Popular amenities for house rentals in Windsor

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Glen Ellen

5 out of 5 average rating, 136 reviews

Tuscan Wine Country Villa sleeps 6

Home in Forestville

4.87 out of 5 average rating, 286 reviews

Hazels Hideaway Hot Tub Redwoods Bonus Room

Guest favourite

Home in Sebastopol

4.98 out of 5 average rating, 166 reviews

Sebastopol Gem, The Birdhouse. Hottub. Pool. Views

Guest favourite

Home in Santa Rosa

4.96 out of 5 average rating, 175 reviews

Happy House w/large pool, hot tub & chefs kitchen

Home in Santa Rosa

4.86 out of 5 average rating, 202 reviews

Hot Tub/Pool ~ Walk To Wine, Shops & Restaurants

Guest favourite

Home in Glen Ellen

4.96 out of 5 average rating, 176 reviews

Stay on a Vineyard. Great Location. Great Views.

Guest favourite

Home in Sonoma

4.95 out of 5 average rating, 158 reviews

Casa Sonoma-Pool, Spa, Bocce

Guest favourite

Home in Santa Rosa

4.98 out of 5 average rating, 104 reviews

Sonoma Green House *Pool*Close to Wine Country

Weekly house rentals

Guest favourite

Home in Jenner

4.96 out of 5 average rating, 158 reviews

Pelican Hill House

Guest favourite

Home in Bodega Bay

4.99 out of 5 average rating, 263 reviews

The Beach House

Guest favourite

Home in Santa Rosa

4.95 out of 5 average rating, 544 reviews

Craftsman 2 blocks from Russian River Brewery!

Guest favourite

Home in Healdsburg

4.98 out of 5 average rating, 114 reviews

Beautiful, Spacious, ArtHaus!

Guest favourite

Home in Forestville

4.97 out of 5 average rating, 108 reviews

Hilltop Haven 🌅 view & hot tub

Guest favourite

Home in Dillon Beach

4.99 out of 5 average rating, 191 reviews

Dillon Beach Nirvana

Guest favourite

Home in Sonoma

4.95 out of 5 average rating, 438 reviews

Zen House on 15 acres

Guest favourite

Home in Healdsburg

4.82 out of 5 average rating, 112 reviews

Redwood River House

Private house rentals

Guest favourite

Home in Santa Rosa

4.9 out of 5 average rating, 164 reviews

Wine Country Retreat: Hot Tub, BBQ, & Mini Golf

Guest favourite

Home in Windsor

4.98 out of 5 average rating, 47 reviews

4-Bedroom Wine Country Home with Pool and Hot Tub

Home in Jenner

4.93 out of 5 average rating, 147 reviews

Pacific Sunset by the beach

Guest favourite

Home in Windsor

4.88 out of 5 average rating, 84 reviews

NEW! Escape to Wine Country! Large Beautiful Home!

Guest favourite

Home in Sebastopol

4.97 out of 5 average rating, 232 reviews

Sonoma County Historical Ranch House on a Vineyard

Guest favourite

Home in Healdsburg

5 out of 5 average rating, 30 reviews

Healdsburg Vineyard Retreat by Inspired in Sonoma

Guest favourite

Home in Dillon Beach

4.99 out of 5 average rating, 338 reviews

Dillon Beach Surf Cottage

Guest favourite

Home in Santa Rosa

4.96 out of 5 average rating, 74 reviews

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

Quick stats about house rentals in Windsor

Total rentals
100 properties
Total number of reviews
6K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
70 properties have a dedicated workspace

Destinations to explore