
House vacation rentals in Windsor
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Top-rated house rentals in Windsor
Guests agree: these houses are highly rated for location, cleanliness, and more.

Russian River Luxury Escape | Private Hot Tub
Indulge in luxury at your new modern style home. Unwind in the elegant, open space interior with natural lighting and Forestville's scenery seeping through the windows. Craft culinary creations in the fully stocked kitchen with a spacious island, and relax on the large backyard deck or hot tub. Stay connected with fast Wi-Fi, the dedicated office space, and the electric car charging outlet. Conveniently located near the Russian River, enjoy your space designed for utmost comfort and tranquility.

Gourmet Kitchen in Wine Country w/Hot Tub + Office
There is no better way to enjoy your stay in wine country than sipping on a glass of wine in this this stunning home! The 14ft bifold door invites out to the beautiful spacious yard where you can relax at any of the 4 sitting areas nestled under a beautiful display of lights. Featuring a chef kitchen, an office, large yard for children & pets, spacious bedrooms, stunning master bath, hot tub, fire table, games & more. Just minutes from elite award winning wineries, craft breweries & restaurants

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.

Wine Country Getaway | Hot Tub + Near Park
Located in Santa Rosa, this home is the perfect retreat for families, friends, and anyone looking to relax and enjoy the area. Just one block away, a fantastic new park features a playground for kids and a spacious dog park perfect for outdoor fun. Enjoy a game of billiards, unwind in the garage-turned-game room, or relax in the inviting living space. Step outside to the patio seating area and BBQ grill—ideal for dining under the stars and making unforgettable memories. SVR24-154 Permit 2024

Healdsburg House - Chiquita Road
Relax with the whole family at this peaceful and private home mins to the Healdsburg Square, Montage Resort, and Dry Creek/Alexander Valley Wineries. The updated home features an open concept kitchen, two family rooms, and a sparkling hot tub on 1.5 private acres surrounded by vineyards and oak trees. Cruise your bike to town or head directly out Chiquita Road to some of the world's greatest cycling. 2.4 miles to the Montage Resort. 2.5 miles to the Healdsburg Square. Welcome to Wine Country!

WineCamp - Wine Country - Vineyard View Hot Tub
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 terrace with Sundance spa hot tub and vineyards beyond. This wine and beer themed property is not suitable for children.

Elegant & Spacious Luxury Wine Country Estate
The perfect place for your group to stay in Wine Country! Featuring two large entertaining areas and an additional dining room, this is a great place for fun and relaxation! Play ping pong, pool or poker in our game room, or dine on our spacious patio under the pergola! Relax and soak in our hot tub and enjoy the zen gardens and tranquil water feature, or sip on a glass of wine by the outdoor fire pit. Close to the Sonoma County Airport, wineries, and world-class dining. Welcome home!

Wine Country Escape: Pool & Hot Tub. Fast WiFi
Escape to our stylish Santa Rosa home, your perfect base for wine country! Comfortably sleeps 8 with 4 bedrooms. Relax in the private backyard oasis featuring a pool, soaking hot tub, and a cozy gas fire pit under a gazebo. Centrally located near world-class wineries, breweries, and dining. Ideal for families and friends seeking a memorable getaway in a quiet, convenient neighborhood. We are happy to help plan your trip or arrange a private wine tasting at the house. Just ask!

Winemaker's Delight: 3BD/3BA Russian River Valley
A stylish 3-bedroom vacation rental in the heart of Santa Rosa, owned by passionate winemakers and perfectly located near top Sonoma wineries, tasting rooms, restaurants, and scenic drives. Ideal for up to six guests, this beautifully designed Wine Country retreat features inviting living spaces and three thoughtfully styled bedrooms with plush linens and serene décor, creating the perfect home base for relaxing, exploring, and enjoying the best of Sonoma County.

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.

Russian River Brewcation | Wine Country Stay
Welcome to Russian River Brewcation, your Wine Country retreat in Sonoma County near the renowned Russian River Valley. This inviting home is perfect for relaxed evenings, gathering with friends, and enjoying the laid-back rhythm of Wine Country living. Guests may arrange private in-home wine tastings delivered directly to the property, along with access to curated experiences at select local winery partners. Permit # SVR25-060

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. Your perfect wine country escape awaits!
Popular amenities for Windsor house rentals
House rentals with a pool

Designer Sonoma Getaway with Pool, Hot Tub & Bocce

Historic 1880's Craftsman Style Home with Pool.

Sonoma Retreat w/Pool/Spa/Barn/OD Kitchen/Orchard

Modern mid-century-inspired, Deer Ranch

Sonoma Country Club Wine Country w/ pool

Spectacular Stone Pool/Spa with Views; Near Plaza

Spacious 5 BR 3BA Pool EV Charger Group Getaway

Pool - Hot Tub - Sauna | Wine Country Oasis Views
Weekly house rentals

Riverfront Retreat: Hot Tub, Dock, Kayaks, Bikes

Healdsburg Wine Retreat • Tasting Perks • FirePit

Wine Country Estate

Centrally Located Modern Wine Country Home

Cul-de-Sac | King | BBQ | Stocked | Washer+Dryer

The Longview in Western Sonoma's redwood hills

Near Healdsburg, Sonoma County Wine Retreat

Cozy cabin deep in the redwoods / WiFi & Hot Tub
Private house rentals

Farmhouse with Pool, Hot Tub and Tastings Included

Luxurious 3-Bedroom Home in Healdsburg

Stony Point Ranch Private Home

Blooming Acres, by Vinifera Homes

Healdsburg Farmhouse. Pool, spa, BBQ. Sleeps 10

Forest retreat near Russian River w/ decks

Heart of Wine Country, Cute Cottage w/Hot Tub

Wine Country Gem | Pool | Hot tub | BBQ
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$55,020 GYD | G$62,760 GYD | G$69,036 GYD | G$59,832 GYD | G$64,852 GYD | G$64,016 GYD | G$74,266 GYD | G$73,430 GYD | G$69,455 GYD | G$59,413 GYD | G$88,911 GYD | G$75,312 GYD |
| 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 vacation rentals
Explore 60 vacation rentals in Windsor

Nightly prices starting at
Windsor vacation rentals start at G$6,276 GYD per night before taxes and fees

Verified guest reviews
Over 3,480 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 of Windsor vacation rentals include wi-fi 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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- Muir Woods National Monument
- Lake Berryessa
- Six Flags Discovery Kingdom
- Jenner Beach
- Bolinas Beach
- Goat Rock Beach
- Doran Beach
- Johnson's Beach
- Safari West
- Limantour Beach
- Jack London State Historic Park
- Armstrong Redwoods State Natural Reserve
- Trione-Annadel State Park
- V. Sattui Winery
- Iron Horse Vineyards
- Sonoma Coast State Park
- Charles M. Schulz Museum
- VJB Vineyard & Cellars
- Ledson Winery & Vineyards
- Healdsburg Plaza
- Sonoma State University
- Sugarloaf Ridge State Park
- Oxbow Public Market
- Harbin Hot Springs





