Windsor vacation rentals

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Recommended by KAYAK

Best Windsor vacation rentals

Treat Yourself to a Great Getaway - Windsor - Pool
Treat Yourself to a Great Getaway
Windsor, CA
9.2Wonderful(17)
Condo
$560+
Check availability
Minutes to Dozens of World Class Wineries - 2 Bedroom / 2 Bath - Sleeps 6 - Windsor - Pool
Minutes to Dozens of World Class Wineries - 2 Bedroom / 2 Bath - Sleeps 6
Windsor, CA
9.2Wonderful(13)
Condo
$560+
Check availability
Sonoma County/Wine Country 2 Bed 2 Bath Condominium Resort - Windsor - Pool
Sonoma County/Wine Country 2 Bed 2 Bath Condominium Resort
Windsor, CA
9.6Wonderful(106)
Condo
$338+
Check availability
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6 - Windsor - Pool
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Windsor, CA
9.4Wonderful(14)
Condo
$513+
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Worldmark Windsor 1bd - Windsor - Pool
Worldmark Windsor 1bd
Windsor, CA
9.8Wonderful(4)
House
Spa
$136+
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Brand New Hybrid Trailer for the California Adventurer! - Windsor - Living room
Brand New Hybrid Trailer for the California Adventurer!
Windsor, CA
Caravan
$318+
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Historic Queen Anne Victorian in the Heart of Windsor - Windsor - Living room
Historic Queen Anne Victorian in the Heart of Windsor
Windsor, CA
10Wonderful(7)
House
Free Wi-Fi
$624+
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Wine Country Retreat. Large backyard with pool/spa, outdoor kitchen & fireplace - Windsor - Living room
Wine Country Retreat. Large backyard with pool/spa, outdoor kitchen & fireplace
Windsor, CA
9.9Wonderful(52)
House
Free Wi-Fi
$435+
Check availability
Wine Country Getaway W/ Fire Pit & Hot Tub! - Windsor - Living room
Wine Country Getaway W/ Fire Pit & Hot Tub!
Windsor, CA
9.7Wonderful(9)
House
Free Wi-Fi
$739+
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Healdsburg Winemaker's Home - Windsor - Patio
Healdsburg Winemaker's Home
Windsor, CA
9.2Wonderful(28)
House
Parking
Free Wi-Fi
Pet friendly
$592+
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Cozy home minutes to wineries and Russian River - Windsor - Living room
Cozy home minutes to wineries and Russian River
Windsor, CA
9.7Wonderful(21)
House
Free Wi-Fi
$265+
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Wine Country Get Away - Windsor - Living room
Wine Country Get Away
Windsor, CA
9.7Wonderful(32)
House
Free Wi-Fi
$318+
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Cottage home near the Russian River; county parks; numerous wineries - Windsor - Living room
Cottage home near the Russian River; county parks; numerous wineries
Windsor, CA
9.8Wonderful(85)
House
Free Wi-Fi
$408+
Check availability
Brand New Pool Luxury 4 Bd, 7 Min To Healdsburg! - Windsor - Kitchen
Brand New Pool Luxury 4 Bd, 7 Min To Healdsburg!
Windsor, CA
10Wonderful(1)
House
$387+
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Flora Vina - Country Home with Vineyard Views - Windsor - Kitchen
Flora Vina - Country Home with Vineyard Views
Windsor, CA
10Wonderful(48)
House
Free Wi-Fi
Pet friendly
$1,309+
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Peaceful Windsor Retreat with Private Hot Tub! - Windsor
Peaceful Windsor Retreat with Private Hot Tub!
Windsor, CA
9.9Wonderful(12)
House
Free Wi-Fi
$535+
Check availability
Useful Info

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

December
October
$506
$408
Cheapest month to stay with an average 44% drop in price.
Most expensive month to stay with an average 48% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Windsor vacation rental deals

  • Vacation rentals in Windsor are around 76% more expensive than hotels on average. Search here to compare prices for all accommodation types in Windsor.
  • The best vacation rental properties in Windsor are Flora Vina - Country Home with Vineyard Views (10.0, 48 reviews), Wine Country Retreat. Large backyard with pool/spa, outdoor kitchen & fireplace (9.9, 52), and Cottage home near the Russian River; county parks; numerous wineries (9.8, 85), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Windsor, you should consider visiting during the low season. The cheapest vacation homes in Windsor can be found in December and August.
  • The cheapest night for renting a vacation home in Windsor is Tuesday. In contrast, the most expensive is Sunday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Windsor for 5 days.

FAQs when booking a vacation home in Windsor

  • What types of vacation rentals are available in Windsor?

    There are loads of different property types that you can make your vacation home in Windsor. You’ll find apartments, caravans, condos, cottages and houses.

  • Are there any pet-friendly vacation rentals in Windsor?

    There are a number of dog and pet-friendly Windsor vacation rentals, with around 4% allowing you to bring your pet along with you.

  • How much is a vacation rental in Windsor for tonight?

    In the last 72 hours, users have found Windsor vacation rentals for tonight for as low as $560. Search here for similar prices

  • How much is a vacation rental in Windsor for this weekend?

    In the last 72 hours, users have found Windsor vacation rentals for this weekend for as low as $514 per night. Search here for similar prices

  • How can I find vacation rentals near me in Windsor?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Windsor?

Our map will help you find the perfect place to stay in Windsor by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Windsor