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

Windsor Rentals

From $169 per night (USD)
VRBO
Bike Riding · Golf · Hiking · Lake · Wineries
Bedrooms:
1
Bathrooms:
0
Sleeps:
2
ACTION NEEDED: Please send your "Booking" with -one- name (first & last) of the person who will be responsible for check ...
From $169 per night (USD)
VRBO
From $226 per night (USD)
VRBO
WorldMark Windsor Condo 2BD
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: The WorldMark Windsor resort is located on ten acres with multiple 3-story buildings, all with elevators. Nestl ...
From $226 per night (USD)
VRBO
From $237 per night (USD)
VRBO
Worldmark Windsor, Wine Country 2BR 2Bath Sleeps6 Last Minute Availability!!
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 $237 per night (USD)
VRBO
$Home near Healdsburg w\/ Hot tub & pool$
Click For Pricing
Expedia
Home near Healdsburg w\/ Hot tub & pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This beautiful 4 bedroom home has everything you will need for you wine county vacation! It is located only minutes from ...
Click For Pricing
Expedia
Click For Pricing
VRBO
3 Bedroom Penthouse!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The best way to enjoy a glass of wine is with good company. Whether it's your first visit to wine country or a frequent ...
Click For Pricing
VRBO
$Experience an unforgettable vacation at this 3BR\/3BA resort$
Click For Pricing
Expedia
Experience an unforgettable vacation at this 3BR\/3BA resort
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to the Russian River Valley, one of California's most beautiful and distinctive wine regions. You'll experience ...
Click For Pricing
Expedia
From $228 per night (USD)
VRBO
Worldmark Windsor Condo 1BD
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The WorldMark Windsor resort is located on ten acres with multiple 3-story buildings, all with elevators. Nestl ...
From $228 per night (USD)
VRBO
$Windsor getaway w\/ heated pool$
Click For Pricing
Expedia
Windsor getaway w\/ heated pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This newly remolded home provides the perfect spacious getaway for your family and friends. It features 3 bedrooms, 2.5 ...
Click For Pricing
Expedia
From $507 per night (USD)
VRBO
Brand New Listing – Windsor “Winetopia” Getaway
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to ’Winetopia’ - Walking distance to Russian River Brewery, Windsor Golf course, a short drive to Sonoma County ...
From $507 per night (USD)
VRBO
$Gorgeous 4 bedroom w\/ hot tub in Windsor$
From $417 per night (USD)
Expedia
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 ...
From $417 per night (USD)
Expedia
From $218 per night (USD)
VRBO
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 $218 per night (USD)
VRBO
$5BD\/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley$
From $570 per night (USD)
Expedia
5BD\/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley
Bedrooms:
5
Bathrooms:
5
Sleeps:
15
11min from Healdsburg Plaza, in a quiet Windsor neighborhood, this 3,575 sq. ft. home is perfect for your next Sonoma Co ...
From $570 per night (USD)
Expedia
From $886 per night (USD)
VRBO
BRAND NEW Luxury 4 bd, 7 min to Healdsburg!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
** This home is professionally managed by Menth Vacation Management. Let Menth Vacation Management handle your entire Wi ...
From $886 per night (USD)
VRBO
Click For Pricing
Expedia
Spacious, Modern, Convenient Wine Country Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to our luxurious, modern, and spacious, wine country home! Conveniently located, this home is walking distance t ...
Click For Pricing
Expedia
From $284 per night (USD)
VRBO
NEW! Local Winemaker's 6 BDRM & VIP Wine Tasting!
Bedrooms:
3
Bathrooms:
6
Sleeps:
10
Welcome to our exquisite 6-bedroom home, owned by a passionate Healdsburg local wine maker, nestled in the heart of Wind ...
From $284 per night (USD)
VRBO
$Island Vacation House w\/ Pool Minutes to Downtown$
Click For Pricing
Expedia
Island Vacation House w\/ Pool Minutes to Downtown
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
This spacious, luxurious, 5 bedroom, Wine Country home has it all. Enjoy the stunning backyard featuring a tiki style ba ...
Click For Pricing
Expedia
$Spacious Wine Country Getaway w\/ Private Backyard, Updated Kitchen & AC$
From $374 per night (USD)
VRBO
Spacious Wine Country Getaway w\/ Private Backyard, Updated Kitchen & AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Lord Manor Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $374 per night (USD)
VRBO
From $464 per night (USD)
Expedia
Corner-Lot Beauty | Gourmet Kitchen | Fenced Yard with Private Hot Tub
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summer Oasis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $464 per night (USD)
Expedia
Click For Pricing
VRBO
BottleRock-Ready 2 Bd Worldmark Resort sleeps 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The resort is located on ten acres with multiple 3-story buildings, all with elevators. Nestled into the Russian River V ...
Click For Pricing
VRBO
$Comfortable home with a patio, WiFi, central AC, and a washer\/dryer$
From $342 per night (USD)
Expedia
Comfortable home with a patio, WiFi, central AC, and a washer\/dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Wine Country Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $342 per night (USD)
Expedia
From $204 per night (USD)
VRBO
Delightful home near downtown with gas grill, fast WiFi, garden, patio & AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Wine Country Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $204 per night (USD)
VRBO
$Wine Country Getaway W\/ Fire Pit & Hot Tub!$
From $687 per night (USD)
Expedia
Wine Country Getaway W\/ Fire Pit & Hot Tub!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover This spacious home in the beautiful Sonoma Wine Country. This 3 bedroom (1 bedroom downstairs), 2 bathroom home ...
From $687 per night (USD)
Expedia
$Beautiful Home w\/ Hot tub close to Healdsburg$
From $475 per night (USD)
VRBO
Beautiful Home w\/ Hot tub close to Healdsburg
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This home is located just minutes from downtown Windsor. It features 3 large bedrooms and a pull out sofa to sleep up to ...
From $475 per night (USD)
VRBO
From $100 per night (USD)
Expedia
Private Cottage 5 minutes from Downtown Healdsburg and Windsor on country lane
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Stay in Sonoma County close to downtown Healdsburg and Windsor in a private gated cottage. This cottage has one bedroom ...
From $100 per night (USD)
Expedia
From $171 per night (USD)
VRBO
Restored country home with private hot tub, amazing garden patio & firepit
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Red Rooster Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $171 per night (USD)
VRBO
From $169 per night (USD)
Expedia
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 $169 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Brand New Hybrid Trailer for the California Adventurer!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to your home away from home! We have a brand new 2022 Flagstaff Shamrock Travel Trailer fully outfitted and read ...
From $250 per night (USD)
VRBO
From $299 per night (USD)
VRBO
Stevie Nicks, Megan thee Stallion, Sheeran, Pearl Jam, Bottlerock Napa 2024
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bottlerock 2024 in Napa Valley. Combine with second resort listing for larger groups. You'll have an unforgettable exper ...
From $299 per night (USD)
VRBO
From $450 per night (USD)
VRBO
Stevie Nicks, Megan thee Stallion, Sheeran, Pearl Jam, Bottlerock Napa 2024
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Bottlerock 2024 in Napa Valley. Combine with second resort listing for larger groups. You'll have an unforgettable exper ...
From $450 per night (USD)
VRBO
$1890s Historic Gem: Casa Dela Esperanza - 6BD\/4BA$
From $1308 per night (USD)
Expedia
1890s Historic Gem: Casa Dela Esperanza - 6BD\/4BA
Bedrooms:
4
Bathrooms:
6
Sleeps:
21
You're just a stone's throw away from the heart of Windsor, where you can discover local wineries, parks, and the vibran ...
From $1308 per night (USD)
Expedia
From $308 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 $308 per night (USD)
VRBO
From $247 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 $247 per night (USD)
Expedia
From $215 per night (USD)
VRBO
Gorgeous Resort in California Wine Country, Windsor!
Bedrooms:
1
Bathrooms:
0
Sleeps:
2
Located in the Russian River Valley, one of California's most beautiful and distinctive wine regions, WorldMark Windsor ...
From $215 per night (USD)
VRBO
From $462 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 $462 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 $308 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 $308 per night (USD)
Expedia
From $352 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 $352 per night (USD)
VRBO
$Heart of Wine Country, Cute Cottage w\/Hot Tub\n$
From $406 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 $406 per night (USD)
Expedia
$5BD WineCountry Home w\/ HotTub, BBQ, & Billiards$
From $478 per night (USD)
Expedia
5BD WineCountry Home w\/ HotTub, BBQ, & Billiards
Bedrooms:
3
Bathrooms:
5
Sleeps:
16
Summary: Welcome to our spacious 5-bedroom Wine Country home! Ideal for family getaways, it boasts a hot tub, game roo ...
From $478 per night (USD)
Expedia
$Gourmet Kitchen in Wine Country w\/Hot Tub + Office$
From $628 per night (USD)
Expedia
Gourmet Kitchen in Wine Country w\/Hot Tub + Office
Bedrooms:
3
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 $628 per night (USD)
Expedia
From $309 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 $309 per night (USD)
VRBO
$Luxury Home with Pool\/Jacuzzi and vineyard views close to Healdsburg Plaza$
From $825 per night (USD)
VRBO
Luxury Home with Pool\/Jacuzzi and vineyard views close to Healdsburg Plaza
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to your dream vacation getaway, where indoor and outdoor entertainment and relaxation seamlessly merge. This 3 b ...
From $825 per night (USD)
VRBO
From $255 per night (USD)
VRBO
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 $255 per night (USD)
VRBO
Click For Pricing
Expedia
Windsor Wine Country Farmhouse
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Enjoy a stylish experience at this centrally-located Windsor Wine Country Farmhouse! The property features 4 bedrooms an ...
Click For Pricing
Expedia
$WM Windsor 3 Bedroom Condo. Sleeps 8\n$
From $233 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 $233 per night (USD)
VRBO
From $226 per night (USD)
VRBO
Beautiful Wine🍷 Country! Exquisite Getaway!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Professionally managed resort (Worldmark) featuring 2 bedrooms & 2 bathrooms. Bedroom 1 has a king bed; Bedroom 2 has 2 ...
From $226 per night (USD)
VRBO
From $494 per night (USD)
VRBO
NEW Family Friendly Wine Country home with hot tub, pool, fire pit
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
New to VRBO, this 4 bed 3 bath home is the perfect place for a weekend getaway in Wine Country. Inside you will find fou ...
From $494 per night (USD)
VRBO
$Flexible check in \/check out 4 bedrooms\/5 beds\/3 bathrooms Wine Country Retreat$
From $497 per night (USD)
VRBO
Flexible check in \/check out 4 bedrooms\/5 beds\/3 bathrooms Wine Country Retreat
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Wine Country Retreat Casa de Vino is the house ideal for large families and entertaining friends. We furnished our home ...
From $497 per night (USD)
VRBO
From $214 per night (USD)
VRBO
Escape to Golf & Wine Paradise:Stunning Home in the Heart of Wine Country
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Welcome to our vibrant VRBO listing, offering an ideal setting for gatherings with family, friends, or colleagues in the ...
From $214 per night (USD)
VRBO
From $188 per night (USD)
VRBO
Windsor Resort 3bd Deluxe
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 $188 per night (USD)
VRBO
From $239 per night (USD)
VRBO
Windsor Resort 3bd Penthouse
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Please send the full name of the person checking in, as on the ID that will be shown when making your booking request. ...
From $239 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $505 per night (USD)
VRBO
Peaceful 4 Bed 2 Bath Home with Hot Tub
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 $505 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $1016 per night (USD)
VRBO
The Oak House - Pool+Spa 5 mins to Healdsburg
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Escape to wine country in this new vacation rental, just 5 minutes to Healdsburg! This home boasts a spacious main house ...
From $1016 per night (USD)
VRBO
From $189 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 $189 per night (USD)
VRBO
$Sonoma County Wine Country Home 4b\/2.5 5min to healdsburg$
From $384 per night (USD)
VRBO
Sonoma County Wine Country Home 4b\/2.5 5min to healdsburg
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Make some memories at this unique and family-friendly place minutes from Healdsburg and Santa Rosa.My home has 4 bedroom ...
From $384 per night (USD)
VRBO
From $154 per night (USD)
VRBO
Windsor Deluxe Resort 1bdr
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Please send the full name of the person checking in, as on the ID that will be shown when making your booking request. ...
From $154 per night (USD)
VRBO
From $160 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 $160 per night (USD)
VRBO
From $210 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 $210 per night (USD)
VRBO
From $600 per night (USD)
VRBO
Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Our architect remodeled (2021), elegant Farmhouse with great room and fireplace, is simply perfect throughout. This uni ...
From $600 per night (USD)
VRBO
From $384 per night (USD)
Expedia
Milk barn Magic: Vineyard Escape with 2 Bedrooms
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Vineyard Vintage: Experience History in our Historic Milk Barn Welcome to our charming vacation rental in Forestville, ...
From $384 per night (USD)
Expedia
From $710 per night (USD)
VRBO
Vineyard Views, Outdoor Kitchen, Hot Tub & Bocce Court
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This Healdsburg home was completely remodeled in 2020 and is perfectly located amongst vineyards, mountain views, redwoo ...
From $710 per night (USD)
VRBO
From $595 per night (USD)
Expedia
Oak Leaf Retreat - 5 Acres, Spa & Vineyards! Peaceful.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
***FOR MORE THAN 4 GUESTS, WE CHARGE $75/night FOR EACH ADDITIONAL GUEST.*** Nestled on 5+ acres at the end of a seclud ...
From $595 per night (USD)
Expedia
From $255 per night (USD)
VRBO
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 $255 per night (USD)
VRBO
$New Sonoma County Station Home\n\n$
From $592 per night (USD)
Expedia
New Sonoma County Station Home\n\n
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
** This home is professionally managed by Menth Vacation Management. Let Menth Vacation Management handle your entire Wi ...
From $592 per night (USD)
Expedia
From $1200 per night (USD)
VRBO
Luxury Sonoma County wine country retreat just 10 minutes from Healdsburg.
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
This 4 bedroom 4.5 bath home is a blend of gracious design, warmth and comfort. Open floor plan in great room, dining ...
From $1200 per night (USD)
VRBO
From $1302 per night (USD)
Expedia
New! Wine Country Family Oasis: Serene Vineyard Views, Pet-Friendly Retreat
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Welcome to your luxurious Sonoma getaway! Amidst picturesque vineyards, this spacious property hosts 10 guests. Indulge ...
From $1302 per night (USD)
Expedia
From $1295 per night (USD)
VRBO
Estate House overlooking cult Russian River Vineyard
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Stay in a luxurious Wine Country estate home overlooking and surrounded by the world famous Kasim Pinot Noir Vineyard. L ...
From $1295 per night (USD)
VRBO
From $2450 per night (USD)
Expedia
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 $2450 per night (USD)
Expedia
From $1016 per night (USD)
VRBO
Hidden Pocket - 1.6 Acres of Resort-like Living Minutes from Healdsburg Plaza
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Is it possible to at once be away from it all and at the center of it all? It is if you spend your wine country vacatio ...
From $1016 per night (USD)
VRBO
From $1621 per night (USD)
Expedia
Amazing Resort-like Estate Near Healdsburg, CA
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
New modern wine country vacation getaway on 10 beautiful acres surrounded by views of mountains, farms and vineyards. 3+ ...
From $1621 per night (USD)
Expedia
From $663 per night (USD)
VRBO
Estrella by AvantStay | Secluded Spanish-Style Estate on 7 Acres of Vineyards
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Welcome to Estrella, an AvantStay home! Retreat to seclusion and relaxation in this spectacular 7-acre European-style v ...
From $663 per night (USD)
VRBO
From $224 per night (USD)
Expedia
A - Russian river brewery, wineries 7 mins!
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Only minutes from Wine, Beer and amazing chef's in the northern Sonoma county region. This townhouse is located in an id ...
From $224 per night (USD)
Expedia
$C - Wineries\/breweries seconds away$
From $149 per night (USD)
VRBO
C - Wineries\/breweries seconds away
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Great location for a wine country getaway! Please use the Airbnb app for self check-in instructions! The owner is sever ...
From $149 per night (USD)
VRBO
From $134 per night (USD)
Expedia
D - Enjoy cabin feels minutes from town!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Great location for a wine country getaway! Please use the VRBO app/website for self-check-in instructions! The owner is ...
From $134 per night (USD)
Expedia
From $149 per night (USD)
VRBO
B - Wine Country Getaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Great Townhouse for a wine country getaway. Please use the Airbnb app for self check-in instructions! The owner is seve ...
From $149 per night (USD)
VRBO
Click For Pricing
Expedia
Grigio by AvantStay | Upscale Sonoma Escape
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Luxury and comfort are yours from the moment you arrive at Grigio. Just a short drive from dozens of nearby vineyards an ...
Click For Pricing
Expedia
Click For Pricing
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 ...
Click For Pricing
Expedia
From $477 per night (USD)
Expedia
Wine Country Backyard Delight
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This wonderful Wine Country Home is waiting for you. 3 bedrooms, and two full bathrooms, plus a backyard private room. ...
From $477 per night (USD)
Expedia
From $1200 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 $1200 per night (USD)
VRBO
From $433 per night (USD)
Expedia
Charming farmhouse amongst the vines
Bedrooms:
4
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 $433 per night (USD)
Expedia
From $438 per night (USD)
VRBO
Healdsburg: Wine Country Retreat-Serenity, Swimming and Solitude
Bedrooms:
3
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 $438 per night (USD)
VRBO
From $149 per night (USD)
Expedia
E - Tiny Home, Big Feel - Just minutes from town and Sonoma County Airport!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Great location for a wine country getaway at an affordable rate! Perfect for a Romantic Getaway for Two! Or a perfect ...
From $149 per night (USD)
Expedia
Click For Pricing
VRBO
Wine Country Getaway with Hot Tub
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This recently renovated 3BR/3BA homes boasts a private hot tub and a beautifully updated floorplan in the heart of wine ...
Click For Pricing
VRBO
From $1395 per night (USD)
Expedia
Heart of Healdsburg
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Vacation in one of the most beautiful areas of the wine country. Chalk Hill Rise is a sprawling 4500 square-foot estate ...
From $1395 per night (USD)
Expedia
From $773 per night (USD)
VRBO
Bella Fattoria-HBG Farm to Table Hideaway
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Welcome to our Beautiful Farm known as Bella Fattoria! A modest yet majestic hideaway in Healdsburg- In the Heart of Son ...
From $773 per night (USD)
VRBO
From $1360 per night (USD)
Expedia
Private Vineyard Residence - 12 minutes from Downtown Healdsburg
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Watch hot-air balloons floating overhead from this four-bedroom country getaway surrounded by our 40-acre vineyard estat ...
From $1360 per night (USD)
Expedia
From $275 per night (USD)
VRBO
Perfect romantic getaway for two! Private retreat in the countryside.
Bedrooms:
1
Bathrooms:
0
Sleeps:
2
Our private boho cottage was completely remodeled from the ground up in 2021 and feels completely new and fresh with a l ...
From $275 per night (USD)
VRBO
Click For Pricing
Expedia
Vineyard View Wine Country Retreat
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Set up for 6 people to enjoy the spacious home right on the vineyard. Enjoy the Chefs kitchen or dine out in the plentif ...
Click For Pricing
Expedia
Click For Pricing
Expedia
Coppola by AvantStay | Explore The Wineries Near This Gorgeous Healdsburg Home!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Coppola, an AvantStay home! Located in lovely Healdsburg, this home is the ultimate stay for a good time. Th ...
Click For Pricing
Expedia
From $1762 per night (USD)
Expedia
The Quails Crossing-Healdsburg Vineyard Home
Bedrooms:
6
Bathrooms:
4
Sleeps:
8
Brand new modern luxury home designed to maximize the natural beauty & surrounding calm. Perched on a hill surrounded by ...
From $1762 per night (USD)
Expedia
From $731 per night (USD)
VRBO
The Dragonfly- Healdsburg Oasis
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Welcome to The Dragonfly, an exquisite oasis of luxury nestled in the heart of wine country. This sophisticated vacation ...
From $731 per night (USD)
VRBO
From $261 per night (USD)
Expedia
Guesthouse on gated 22 acre family ranch, vineyard
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nestled in the foothills between Healdsburg and Windsor, enjoy a soothing stay in this beautiful Casita, located inside ...
From $261 per night (USD)
Expedia
From $175 per night (USD)
VRBO
Vineyard View Retreat near Russian River
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Settled on a hill among mature oak trees and acres of vineyards, our home is perfect for a quick getaway or a longer ret ...
From $175 per night (USD)
VRBO
From $511 per night (USD)
Expedia
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 $511 per night (USD)
Expedia
From $80 per night (USD)
VRBO
Cozy Cottage Perfect for the longer Staycation
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Kick back & relax in this calm, stylish space. This Cottage is perfect for a longer staycation or for any one or two peo ...
From $80 per night (USD)
VRBO
From $1096 per night (USD)
Expedia
Modern Family Friendly Farmhouse with Pool, Spa & Fire pit
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 $1096 per night (USD)
Expedia

Search Your Destination Now!

Windsor Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 198 Rentals