Darkest Travel - Vacation Rentals in Windsor

Flora Vina - Country Home with Vineyard Views From US $1,012
         

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10.0 (2 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • View
Holiday Inn Express® Windsor Sonoma Wine Country by IHG From US $108
         

Cottage home near the Russian River; county parks; numerous wineries From US $395
         

Flora Vina - Country Home with Vineyard Views From US $1,039
         

10.0 (52 Reviews)
House
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  • Pet Friendly
Wine Country Getaway W/Fire Pit & Hot Tub! From US $600
         

10.0 (26 Reviews)
House
  • Air Conditioner
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  • TV
Historic Queen Anne Victorian in the Heart of Windsor From US $485
         

Luxury Places to Stay in Windsor

Over 242+ Luxury Places to Stay in or Near Windsor
Modern Hilltop Healdsburg Residence With 360' Views From US $2,844
         

Villa Terra Bella, by Vinifera Homes From US $1,256
         

10.0 (7 Reviews)
Villa
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  • Pet Friendly
Herb Retreat From US $1,241
         

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9.0 (1 Review)
House
  • Air Conditioner
  • Pool
  • Balcony/Terrace
Exceptional Estate Vineyards in Healdsburg Sonoma County From US $1,222
         

9.4 (3 Reviews)
Villa
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  • Balcony/Terrace
Eastside Eden Wine Tastings Included From US $1,100
         

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10.0 (1 Review)
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  • Air Conditioner
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  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Windsor

Over 143+ Top-Rated Vacation Rentals with a Pool in or Near Windsor
Visit the Russian River Valley in style! From US $272
         

10.0 (47 Reviews)
Resort
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5bd/4ba w/Poolside Guest House - near Healdsburg From US $328
         

10.0 (40 Reviews)
House
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  • Pet Friendly
Awesome summers and gorgeous winters! From US $241
         

10.0 (22 Reviews)
Resort
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  • Pool
Windsor Deluxe Resort 3bdr From US $264
         

10.0 (6 Reviews)
Resort
  • Air Conditioner
  • Pool
  • TV
Postcard-perfect setting! From US $306
         

10.0 (4 Reviews)
Resort
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  • Parking
  • Pool
Breathtaking in all directions! From US $266
         

10.0 (4 Reviews)
Resort
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  • Pool
Gorgeous region . Wonderful Times ! From US $238
         

10.0 (4 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Windsor

Over 42+ Pet-Friendly Vacation Rentals in or Near Windsor
Casa de la Esperanza: 1890s Historic Gem - 5BD/3BA From US $1,008
         

10.0 (11 Reviews)
House
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  • Pet Friendly
Stylish Vineyard Living at Winemakers Estate From US $653
         

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New
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Heart of Wine Country, Cute Cottage w/Hot Tubn From US $380
         

9.4 (29 Reviews)
House
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  • Pet Friendly
Private Vineyard Estate | Sleeps 10 From US $1,033
         

9.4 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Wine Country Home of Healdsburg Wine Maker From US $822
         

9.2 (24 Reviews)
House
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  • Parking
  • Pet Friendly
Peaceful 4 Bed 2 Bath Home with Spacious Backyard From US $319
         

9.4 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Windsor on PetFriendly.io

Large Vacation Homes & Villas in Windsor

Over 21+ Large Vacation Homes & Villas in or Near Windsor
Healdsburg Winemaker's Home From US $586
         

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New
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4-Bedroom Home with Pool & Hot Tub in Wine Country From US $1,094
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Windsor home on golf course w/hot tub From US $437
         

9.8 (41 Reviews)
House
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  • Parking
  • Pet Friendly
Beautiful 4 bedroom home w/luxurious furnishings From US $429
         

Home near Healdsburg w/ Hot tub & pool From US $402
         

4.8 (4 Reviews)
House
  • Air Conditioner
  • Pool
  • View

Wheelchair Accessible Vacation Homes in Windsor

Over 90+ Wheelchair Accessible Vacation Homes in or Near Windsor
Holiday Inn Express Windsor Sonoma Wine Country by IHG From US $213
         

Hampton Inn & Suites Windsor - Sonoma Wine Country From US $127
         

9.2 (1004 Reviews)
Hotel
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  • Pool
Treat Yourself to a Great Getaway From US $308
         

9.6 (63 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Windsor Varoom and Airbnb Places to Stay Under $200

Over 14+ Windsor Varoom and Airbnb Places to Stay Under $200
WorldMark Windsor From US $123
         

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8.8 (118 Reviews)
Resort
  • Air Conditioner
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  • Pool
Holiday Inn Windsor Wine Country by IHG From US $109
         

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9.0 (1007 Reviews)
Hotel
  • Air Conditioner
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Combs Wine Sippin Escape From US $159
         

9.8 (8 Reviews)
Apartment
  • Air Conditioner
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  • Pet Friendly
Charming NEW Home in Windsor From US $100
         

6.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Windsor

Over 79+ Instantly Bookable Vacation Homes in or Near Windsor
WorldMark Windsor - Studio From US $213
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • TV
BRAND NEW POOL Luxury 4 bd, 7 min to Healdsburg! From US $357
         

WorldMark Windsor - 1 Bedroom Accessible From US $238
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • Pool
  • TV
Wine Country Get Away From US $246
         

9.8 (33 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Cozy home minutes to wineries and Russian River From US $261
         

WorldMark Windsor - 2 Bedroom Accessible From US $280
         

9.2 (5 Reviews)
Condo
  • Air Conditioner
  • Pool
  • TV
WorldMark Windsor - 1 Bedroom From US $232
         

9.0 (4 Reviews)
Condo
  • Air Conditioner
  • Pool
  • TV

About Windsor Vacation Rentals

With more than 251 Windsor vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Darkesttravel and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Windsor.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Darkesttravel Windsor, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Windsor. Places to stay near Windsor are 655.38 ft² on average, with prices averaging $479 a night.

Darkesttravel makes it easy and safe to find and compare vacation rentals in Windsor with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Windsor

Type Count
Vacation Homes 97
Resorts 71
Holiday Apartments 19
Hotels with Suites 6
Villas 6
Others 4
Cottages 3

Use these Quick Filters to Find a Vacation Rental in Windsor

Pro Tip: Darkesttravel makes it easy to compare the best listings on Darkesttravel homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Darkesttravel homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Windsor.

Weather in Windsor

View the weather forecast for Windsor before booking your Windsor Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 33°F
March - May
High 73°F       Low 43°F
June - August
High 85°F       Low 51°F
September - November
High 84°F       Low 46°F