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

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.

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.

Botany House Designer Home with Hot Tub
Discover your Wine Country sanctuary in this lush, design-forward Santa Rosa retreat. With a chef’s kitchen, a six-person hot tub, a fire pit, and Restoration Hardware furnishings, every detail is crafted for comfort and style. Perfectly located near wineries, Michelin-star dining, and redwood adventures, it’s ideal for families or friends seeking luxury and connection. Book your escape today. We are pet-friendly. Message us on Social Media at Inspired in Sonoma for Inspiration and Tips.

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

West End Neighborhood Cottage
ID Tax 3099 1 bedroom cottage with a victorian-style interior tucked away with a quiet, shared yard and picnic table. Enjoy staying walking distance from historic Downtown where you'll find numerous small shops, microbreweries, bars, restaurants, gardens, book stores, coffee and local events. Blocks from multiple modes of public transportation makes this location perfect if you want to venture farther and explore the diverse landscapes of Sonoma County. Quiet Hours 9PM to 7AM

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.

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, heated floor and bidet. A small cozy two bedroom with many amenities and thoughtful touches.

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!

Grape Expectations: A Winemaker’s Country Retreat
Welcome to our warm and modern 3-bedroom, 2.5-bath retreat—where style meets eco-friendly convenience! Nestled in a peaceful neighborhood, this thoughtfully designed home comes equipped with a Tesla Universal EV charger, making it ideal for families, friends, or business travelers. Whether you’re here for a relaxing getaway, a weekend escape, or a work trip, you’ll find everything you need for a seamless and comfortable stay. PERMIT NUMBER: SVR25-025

Wine Country Home With Mini Golf & More
Welcome to the ultimate home for fun and relaxation with your favorite people! Gather around the crackling fireplace for cozy nights, splash and soak in the hot tub with jets that hit just right, and fire up the BBQ for a backyard feast. End the night roasting marshmallows at the fire pit or challenge each other to a round of mini-golf right at home. Perfect for families and friends to laugh, relax, and make unforgettable memories together!
Popular amenities for house rentals in Windsor
House rentals with a pool

Luxe WineCountry getaway with Pool, hottub & Bocce

Modern mid-century-inspired, Deer Ranch

Pool•Spa•6 Bikes•1mi to Town•Fire Pit•ShuffleBoard

Sebastopol Gem, The Birdhouse. Hottub. Pool. Views

Happy House Getaway - Pool, Hot Tub & Wine Country

Vineyard Home • Press Pick • Walk to Wineries

Pacific Gardens Retreat

The Deer Retreat – Privacy and Comfort
Weekly house rentals

Pelican Hill House

Russian River Valley Brew-cation Home

4bd Family-Friendly*Play Area*Hot Tub*

The Beach House

Craftsman 2 blocks from Russian River Brewery!

Beautiful, Spacious, ArtHaus!

Adventures surround this charming 2bedroom home.

Dillon Beach Nirvana
Private house rentals

Vineyard Oasis: Luxury Home in the Heart of Sonoma

Centrally Located Modern Wine Country Home

Modern Wine Country Cottage

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

Walk to Russian River - Casa Del Rio - Unit A

Redwood stay w/Spacious Kitchen & lots of Windows

Near Healdsburg, Sonoma County Wine Retreat

Private Vineyard Haven | Wine Tastings Included
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $362 SGD | $343 SGD | $361 SGD | $367 SGD | $398 SGD | $393 SGD | $456 SGD | $450 SGD | $426 SGD | $442 SGD | $445 SGD | $385 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 Windsor

Total holiday rentals
Explore 70 holiday rentals in Windsor

Nightly prices starting at
Windsor holiday rentals start at $39 SGD per night before taxes and fees

Verified guest reviews
Over 3,730 verified reviews to help you choose

Family-friendly holiday rentals
50 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
40 properties have a dedicated workspace

Wifi availability
70 of Windsor holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Windsor rentals

4.9 Average rating
Windsor stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with a washing machine and dryer Windsor
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