Lakes Resorts - Vacation Rentals in Windsor

WorldMark Windsor From US $123
         

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8.8 (118 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Visit the Russian River Valley in style! From US $321
         

10.0 (47 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Gorgeous Resort in California Wine Country, Windsor! From US $462
         

Gorgeous Resort in California Wine Country, Windsor! From US $356
         

Gorgeous Resort in California Wine Country, Windsor! From US $426
         

Luxury Places to Stay in Windsor

Over 244+ Luxury Places to Stay in or Near Windsor
Modern Hilltop Healdsburg Residence With 360' Views From US $2,888
         

The Quails Crossing-Healdsburg Vineyard Home From US $2,122
         

10.0 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
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
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Elegant Vineyard Living at a Private Wine Country Estate From US $1,172
         

8.4 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Windsor

Over 142+ Top-Rated Vacation Rentals with a Pool in or Near Windsor
Visit the Russian River Valley in style! From US $282
         

10.0 (47 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
5bd/4ba w/Poolside Guest House - near Healdsburg From US $279
         

10.0 (40 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Awesome summers and gorgeous winters! From US $257
         

10.0 (22 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Windsor Deluxe Resort 3bdr From US $262
         

10.0 (6 Reviews)
Resort
  • Air Conditioner
  • Pool
  • TV
Windsor Deluxe Resort 1bdr From US $199
         

10.0 (5 Reviews)
Resort
  • Air Conditioner
  • Pool
  • TV
Postcard-perfect setting! From US $298
         

10.0 (4 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Breathtaking in all directions! From US $282
         

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

Pet-Friendly Vacation Rentals in Windsor

Over 43+ Pet-Friendly Vacation Rentals in or Near Windsor
Flora Vina - Country Home with Vineyard Views From US $1,039
         

10.0 (52 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Stylish Vineyard Living at Winemakers Estate From US $653
         

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New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Gourmet Kitchen in Wine Country w/Hot Tub + Office From US $1,039
         

9.8 (9 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Heart of Wine Country, Cute Cottage w/Hot Tubn From US $386
         

9.4 (29 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Wine Country Home of Healdsburg Wine Maker From US $722
         

9.2 (24 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Peaceful 4 Bed 2 Bath Home with Spacious Backyard From US $437
         

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 22+ Large Vacation Homes & Villas in or Near Windsor
Charming 4-bedroom villa with AC in Windsor
New
From US $403
         

New
Villa
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Healdsburg Winemaker's Home From US $586
         

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New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa Terra Bella, by Vinifera Homes From US $1,436
         

10.0 (7 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
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
  • Air Conditioner
  • Parking
  • Pet Friendly
Beautiful 4 bedroom home w/luxurious furnishings From US $429
         

Wheelchair Accessible Vacation Homes in Windsor

Over 85+ Wheelchair Accessible Vacation Homes in or Near Windsor
Hampton Inn & Suites Windsor-Sonoma Wine Country From US $211
         

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8.5 (210 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Hampton Inn & Suites Windsor - Sonoma Wine Country From US $135
         

9.2 (1001 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Treat Yourself to a Great Getaway From US $269
         

9.6 (65 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Worldmark Windsor Condo 1BD From US $206
         

9.6 (4 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Windsor Varoom and Airbnb Places to Stay Under $200

Over 15+ Windsor Varoom and Airbnb Places to Stay Under $200
WorldMark Windsor - Studio From US $196
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • TV
Holiday Inn Windsor - Wine Country by IHG From US $178
         

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8.4 (166 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Holiday Inn Express® Windsor Sonoma Wine Country by IHG From US $117
         

WorldMark Wine Country Windsor Sonoma County 1 Bedroom
New
From US $113
         

New
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Combs Wine Sippin Escape From US $159
         

9.8 (8 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • 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 76+ Instantly Bookable Vacation Homes in or Near Windsor
Historic Queen Anne Victorian in the Heart of Windsor From US $493
         

BRAND NEW POOL Luxury 4 bd, 7 min to Healdsburg! From US $412
         

Wine Country Get Away From US $258
         

9.8 (34 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Cozy home minutes to wineries and Russian River From US $261
         

WorldMark Windsor - 2 Bedroom Twin From US $285
         

9.0 (6 Reviews)
Condo
  • Air Conditioner
  • Pool
  • TV
WorldMark Windsor - 1 Bedroom From US $224
         

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

About Windsor Vacation Rentals

With more than 76 Windsor vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Lakesresorts 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 Lakesresorts 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 146.62 ft² on average, with prices averaging $295 a night.

Lakesresorts 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
Resorts 76

Use these Quick Filters to Find a Vacation Rental in Windsor

Pro Tip: Lakesresorts makes it easy to compare the best listings on Lakesresorts homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Lakesresorts 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