Windsor, California Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Windsor, California on RentalSaver.com!

Windsor Rentals

From $246 per night (USD)
VRBO
Worldmark Windsor Condo 1BD
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The WorldMark Windsor resort is located on ten acres with multiple 3-story buildings, all with elevators. Nestled into t ...
From $246 per night (USD)
VRBO
From $1072 per night (USD)
Expedia
4BD/4BA Heated Pool+Spa+BBQ: 11min Healdsburg & Alexander Valley
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
- Spacious 4BD/4BA 3,200 sq. ft. villa in wine country - Prime location: 11 min to Healdsburg Plaza, 13 min to Alexander ...
From $1072 per night (USD)
Expedia
From $384 per night (USD)
VRBO
BRAND NEW POOL Luxury 4 bd, 7 min to Healdsburg!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: ** This home is professionally managed by LegacyRnR. Let LegacyRnR handle your entire Wine Country get away wee ...
From $384 per night (USD)
VRBO
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Expedia
Spacious, Modern, Convenient Wine Country Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to our luxurious, modern, and spacious, wine country home! Conveniently located, this home is walking distance t ...
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Expedia
From $264 per night (USD)
VRBO
Wine Country Get Away
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This is a comfortable home in a quiet residential neighborhood. There are walking trails through out the neighborhood a ...
From $264 per night (USD)
VRBO
From $362 per night (USD)
Expedia
Wine Country Beautiful Worldmark 2Bedroom Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Windsor is located about an hour north of San Franscico. There you can enjoy all the sights without having to pay high ...
From $362 per night (USD)
Expedia
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VRBO
Gorgeous 4 bedroom w/ hot tub in Windsor
Bedrooms:
3
Bathrooms:
4
Sleeps:
5
This stylish home has every amenity needed for you wine country getaway! It features a large kitchen, perfectly manicure ...
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VRBO
$Heart of Wine Country, Cute Cottage w/Hot Tub\n$
From $437 per night (USD)
Expedia
Heart of Wine Country, Cute Cottage w/Hot Tub\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This little oasis is backed into a quiet creek. It's centrally located, walking distance to downtown, where you can visi ...
From $437 per night (USD)
Expedia
From $324 per night (USD)
VRBO
Gorgeous Resort in California Wine Country, Windsor!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in the Russian River Valley, one of California's most beautiful and distinctive wine regions, WorldMark Windsor ...
From $324 per night (USD)
VRBO
From $282 per night (USD)
Expedia
Gorgeous Resort in California Wine Country, Windsor!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in the Russian River Valley, one of California's most beautiful and distinctive wine regions, WorldMark Windsor ...
From $282 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Gorgeous Resort in California Wine Country, Windsor!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in the Russian River Valley, one of California's most beautiful and distinctive wine regions, WorldMark Windsor ...
From $250 per night (USD)
VRBO
From $590 per night (USD)
Expedia
Gorgeous Resort in California Wine Country, Windsor!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Located in the Russian River Valley, one of California's most beautiful and distinctive wine regions, WorldMark Windsor ...
From $590 per night (USD)
Expedia
From $442 per night (USD)
VRBO
Gorgeous Resort in California Wine Country, Windsor!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Located in the Russian River Valley, one of California's most beautiful and distinctive wine regions, WorldMark Windsor ...
From $442 per night (USD)
VRBO
From $347 per night (USD)
Expedia
Gorgeous Resort in California Wine Country, Windsor!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in the Russian River Valley, one of California's most beautiful and distinctive wine regions, WorldMark Windsor ...
From $347 per night (USD)
Expedia
From $410 per night (USD)
VRBO
Gorgeous Resort in California Wine Country, Windsor!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Located in the Russian River Valley, one of California's most beautiful and distinctive wine regions, WorldMark Windsor ...
From $410 per night (USD)
VRBO
From $961 per night (USD)
Expedia
Casa de la Esperanza: 1890s Historic Gem - 6BD/4BA
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
You're just a stone's throw away from the heart of Windsor, where you can discover local wineries, parks, and the vibran ...
From $961 per night (USD)
Expedia
From $1156 per night (USD)
VRBO
Gourmet Kitchen in Wine Country w/Hot Tub + Office
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
There is no better way to enjoy your stay in wine country than sipping on a glass of wine in this this stunning home! Th ...
From $1156 per night (USD)
VRBO
From $576 per night (USD)
Expedia
“Winetopia” Windsor Getaway - 39 Exceptional Reviews!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
The town of Windsor has banned Short Term Rentals as of June 30, 2025. If you would like to inquire on a longer stay, p ...
From $576 per night (USD)
Expedia
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VRBO
WorldMark Windsor - 3 Bedroom Penthouse Accessible
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This is a full-service resort. Your check-in procedures will model that of a hotel and your room number will be assigne ...
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VRBO
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Expedia
WorldMark Windsor - 3 Bedroom Penthouse
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This is a full-service resort. Your check-in procedures will model that of a hotel and your room number will be assigne ...
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Expedia
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VRBO
WorldMark Windsor - 3 Bedroom Deluxe
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This is a full-service resort. Your check-in procedures will model that of a hotel and your room number will be assigne ...
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VRBO
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Expedia
WorldMark Windsor - 3 Bedroom Accessible
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This is a full-service resort. Your check-in procedures will model that of a hotel and your room number will be assigne ...
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Expedia
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VRBO
3Br/2.5Ba Furnished Townhouse Walk To Town Green
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Upstairs Windsor Town Green condominium with high end furnishings, fireplace, a/c, fireplace, full kitchen, dining and s ...
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VRBO
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Expedia
WorldMark Windsor - 3 Bedroom
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This is a full-service resort. Your check-in procedures will model that of a hotel and your room number will be assigne ...
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Expedia
From $278 per night (USD)
VRBO
WorldMark Windsor - 2 Bedroom Twin
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a full-service resort. Your check-in procedures will model that of a hotel and your room number will be assigne ...
From $278 per night (USD)
VRBO
$WM Windsor 3 Bedroom Condo. Sleeps 8\n$
From $325 per night (USD)
VRBO
WM Windsor 3 Bedroom Condo. Sleeps 8\n
Bedrooms:
0
Bathrooms:
0
Sleeps:
0
This spacious three-bedroom resort suite measures approximately 1,246 square feet. You will enjoy a king bed in the mast ...
From $325 per night (USD)
VRBO
From $364 per night (USD)
VRBO
2 BED 2 BATH UNIT IN WINDSOR, CA - A Superb Sonoma County Stay
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
WorldMark Windsor, located within the Russian River Valley in Sonoma County about an hour outside of San Francisco, is o ...
From $364 per night (USD)
VRBO
From $372 per night (USD)
Expedia
Great Wine Country and Golfing Resort Getaway!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
About this space I'm offering a beautiful fully furnished two bedroom, two bath condo at the WorldMark Resort in Windsor ...
From $372 per night (USD)
Expedia
From $296 per night (USD)
VRBO
5bd/4ba w/ Poolside Guest House - near Healdsburg
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Escape to wine country, just 5 minutes to Healdsburg! This fully furnished 5 bedroom, 4 bathroom single level home is ce ...
From $296 per night (USD)
VRBO
From $216 per night (USD)
VRBO
Windsor Resort 2bdr Queen
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Please send the full name of the person checking in, as on the ID that will be shown when making your booking request. ...
From $216 per night (USD)
VRBO
From $329 per night (USD)
VRBO
WM WIndsor 2 BR Queen
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This spacious two-bedroom resort suite measures approximately 1,023 square feet. You will enjoy a king bed in the master ...
From $329 per night (USD)
VRBO
From $201 per night (USD)
VRBO
Peaceful 4 Bed 2 Bath Home with Spacious Backyard
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Embrace the wine country life style with family and friends at this picturesque peaceful home in the heart of Sonoma Cou ...
From $201 per night (USD)
VRBO
From $217 per night (USD)
VRBO
WM Windsor 1 Bedroom Condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This spacious one-bedroom resort suite measures approximately 822 square feet. You will enjoy a king bed in the bedroom ...
From $217 per night (USD)
VRBO
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Expedia
Escape to Paradise: Stunning Home in the Heart of Wine Country
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Welcome to Your Ultimate Wine Country Home Get ready to unwind, explore, and indulge in the heart of Wine Country! Our ...
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Expedia
From $312 per night (USD)
VRBO
4 bedrooms 5 beds 3 full bathrooms - price depends on the number of rented days.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
A spacious sunlit house is a furnished home for your relax if you have a business trip in this area. With so many activ ...
From $312 per night (USD)
VRBO
From $200 per night (USD)
VRBO
Windsor Deluxe Resort 1bdr
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Please send the full name of the person checking in, as on the ID that will be shown when making your booking request. ...
From $200 per night (USD)
VRBO
From $268 per night (USD)
VRBO
Windsor Deluxe Resort 3bdr
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Please send the full name of the person checking in, as on the ID that will be shown when making your booking request. ...
From $268 per night (USD)
VRBO
From $243 per night (USD)
VRBO
Windsor Deluxe Resort 2bdr
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Please send the full name of the person checking in, as on the ID that will be shown when making your booking request. ...
From $243 per night (USD)
VRBO
From $765 per night (USD)
VRBO
Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Our architect remodeled (2021), elegant Farmhouse with great room and fireplace, is simply perfect throughout. This uni ...
From $765 per night (USD)
VRBO
From $647 per night (USD)
Expedia
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Vineyard Vintage: Experience History in our Historic Milk Barn Welcome to our charming vacation rental in Forestville, ...
From $647 per night (USD)
Expedia
From $1136 per night (USD)
VRBO
Flora Vina - Country Home with Vineyard Views
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
This Spacious one-story home is as dreamy as its own vineyard name, Flora Vina. Located in the Russian River Appellation ...
From $1136 per night (USD)
VRBO
From $258 per night (USD)
Expedia
Chalk Hill Cottage Close to Wineries
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This charming 1 bedroom cottage is perfect for couples looking to explore the famous wine country of Sonoma's Chalk Hill ...
From $258 per night (USD)
Expedia
From $1948 per night (USD)
VRBO
Sonoma Wine Country Home: Pool, Hot Tub & Fun!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Escape to Station House, a luxurious Wine Country retreat in Windsor, CA! This stunning 4-bedroom home boasts a ...
From $1948 per night (USD)
VRBO
From $1130 per night (USD)
Expedia
Wine Country Estate Home
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Consider this country house/chateau your home away from home while you visit Wine Country . This beautiful property has ...
From $1130 per night (USD)
Expedia
From $1210 per night (USD)
VRBO
Luxury home on 85AC Chardonnay Vineyard minutes from Healdsburg
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This is a 3+1 bedroom home that can sleep 6 (plus children on bunk and trendle beds) with 4.5 baths. The property sits ...
From $1210 per night (USD)
VRBO
From $939 per night (USD)
VRBO
Hidden Pocket: Private Sonoma Wine Country Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
The Perfect Wine Country Escape Tucked away at the end of a quiet country road, our resort-style sanctuary offers the u ...
From $939 per night (USD)
VRBO
From $2903 per night (USD)
VRBO
Entire Wine Country Resort Villa #Pool-Spa-Tennis-Wine-Dine#
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Our sprawling estate offers easy access to every wine country amenity imaginable. Watch hot air balloons take off from t ...
From $2903 per night (USD)
VRBO
From $1713 per night (USD)
Expedia
Healdsburg, CA Amazing Resort-like Estate Healdsburg -- 4BD / 3BA
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
New modern wine country vacation getaway on 10 beautiful acres surrounded by views of mountains, farms and vineyards. 4 ...
From $1713 per night (USD)
Expedia
From $273 per night (USD)
VRBO
Windsor 2 Bdrm Condo Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Large 2 Bedroom condo at a resort condo development in beautiful Windsor, California ❤ Free Parking. Free Internet ❤ ★ ...
From $273 per night (USD)
VRBO
From $3514 per night (USD)
Expedia
Healdsburg Calif.: Amazing Resort-like Estate Healdsburg -- 4BD / 3BA
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
New modern wine country vacation getaway near Healdsburg CA, on 10 beautiful acres surrounded by views of mountains, far ...
From $3514 per night (USD)
Expedia
From $420 per night (USD)
VRBO
Vineyard Oasis: Luxury Home in the Heart of Sonoma.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Imagine waking up to panoramic views of vineyards stretching as far as the eye can see. Located just 10 minutes from dow ...
From $420 per night (USD)
VRBO
From $821 per night (USD)
Expedia
Charming house in Healdsburg with Pool and Hot Tub
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your home away from home in Healdsburg with 3 bedrooms. This charming house features 2 queen beds and 1 king bed, perfec ...
From $821 per night (USD)
Expedia
From $1490 per night (USD)
VRBO
Exceptional Estate Vineyards in Healdsburg Sonoma County
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Exceptional Vineyard & winery Estate in Chalk Hill- Russian River Appellation. Designed for indoor/ outdoor living. Sip ...
From $1490 per night (USD)
VRBO
From $817 per night (USD)
Expedia
Healdsburg, sleeps 10, pool, hot tub, gardens, BBQ, Vineyard Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Healdsburg 4BR/3BA Gorgeous Farmhouse. In ground solar heated pool (season only May through September), hot tub with ve ...
From $817 per night (USD)
Expedia
From $177 per night (USD)
VRBO
Great for traveling Nurses!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Due to regulations stays must be 30 plus days. Please inquire! Only minutes from Wine, Beer and amazing chef's ...
From $177 per night (USD)
VRBO
From $137 per night (USD)
Expedia
Peaceful place for traveling nurses!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Due to regulations stays must be 30 plus days. Please inquire! Great location for a wine country getaway! Plea ...
From $137 per night (USD)
Expedia
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VRBO
D - Not available Sum
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Great location for a wine country getaway! Please use the Airbnb app for self check-in instructions! The owne ...
Click For Pricing
VRBO
From $853 per night (USD)
Expedia
Eastside Eden | Tasting at Croix Included!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Experience the beauty of Sonoma County with a stay at this charming farm house. Boasting 3 bedrooms and 3.5 bathrooms, t ...
From $853 per night (USD)
Expedia
From $602 per night (USD)
VRBO
Healdsburg: Wine Country Retreat-Serenity, Swimming and Solitude
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This lovely Windsor Foothills Property is 6 miles southeast of Healdsburg’s famed Plaza and sits on 3+ acres with the se ...
From $602 per night (USD)
VRBO
$WM Windsor 1 Bedroom Condo\n$
From $230 per night (USD)
VRBO
WM Windsor 1 Bedroom Condo\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
✺✺ Free Parking. Free Internet ✺✺ You will enjoy a king bed in the bedroom and one queen Murphy bed in the living room. ...
From $230 per night (USD)
VRBO
From $607 per night (USD)
VRBO
Charming Retreat near Healdsburg – 3 BD + Den, Outdoor Dining
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to your vintage escape nestled in the heart of California's wine country. This delightful 3 bedroom + den, 3 bat ...
From $607 per night (USD)
VRBO
From $1257 per night (USD)
Expedia
Villa Terra Bella, by Vinifera Homes
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Welcome to Villa Terra Bella, your escape in the heart of Wine Country. This European-style villa is surrounded by 7-acr ...
From $1257 per night (USD)
Expedia
From $1301 per night (USD)
VRBO
Luxury Estate Awaits: Your Ultimate Vineyard Escape
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to the Best Region in California: Your Perfect Vineyard Escape Awaits! Nestled in the heart of the Russian Rive ...
From $1301 per night (USD)
VRBO
Click For Pricing
Expedia
E - Not Available Sum
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Great location for a wine country getaway for cheap! Please use the Airbnb app for self check-in instructions! ...
Click For Pricing
Expedia
From $923 per night (USD)
VRBO
The Dragonfly- Complimentary wine tasting at Croix included!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to The Dragonfly, an exquisite oasis of luxury nestled in the heart of wine country. This sophisticated vacation ...
From $923 per night (USD)
VRBO
$Private Vineyard Residence - 10 minutes from Healdsburg\n$
From $1773 per night (USD)
Expedia
Private Vineyard Residence - 10 minutes from Healdsburg\n
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Watch hot-air balloons floating overhead from this four-bedroom country getaway surrounded by our 40-acre vineyard estat ...
From $1773 per night (USD)
Expedia
From $1797 per night (USD)
VRBO
The Quails Crossing-Healdsburg Vineyard Home
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Brand new modern luxury home designed to maximize the natural beauty & surrounding calm. Perched on a hill surrounded by ...
From $1797 per night (USD)
VRBO
From $1181 per night (USD)
Expedia
10 min to Healdsburg - Modern Farmhouse with Pool, Spa & Views
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Situated on 2.5 acres, just minutes from the quaint downtown of Windsor and about 10 minutes from the well known Healdsb ...
From $1181 per night (USD)
Expedia
From $984 per night (USD)
VRBO
Chatthaveli Healdsburg
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
★ PROPERTY HIGHLIGHTS ★ ✔ Poo/Spal: Dip in the pool, relax in the hot tub, and enjoy mountain views! ✔ Space: Relish th ...
From $984 per night (USD)
VRBO
From $289 per night (USD)
VRBO
Vineyard View 2-bedroom 1 bath in Forestville, AC, WIFI, STUNNING VIEWS!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This Forestville apartment boasts 2 inviting bedrooms with 1 king bed and 1 queen bed. Our beautiful 2BR unit is nestled ...
From $289 per night (USD)
VRBO

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Results: 170 Rentals