Windsor Resorts
Cabin
10.0(34 Reviews)
2 Bedrooms
1 Bath
6 Guests
830 ft²
Hot Tub
Parking
Balcony/Terrace
Kitchen
US $203/Night
7 Nights - US $1,420
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1797.57 ft²
- Parking
Internet
Child Friendly
Sports/Activities
US $363/Night
7 Nights - US $2,541
Cottage
1 Bedroom
1 Bath
Oceanfront- Parking
Ocean View- Balcony/Terrace
US $274/Night
7 Nights - US $1,918
Cabin
10.0(32 Reviews)
2 Bedrooms
1 Bath
6 Guests
896 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $203/Night
7 Nights - US $1,420
House
10.0(3 Reviews)
1 Bedroom
1 Bath
2 Guests
1001.04 ft²
- Parking
- Balcony/Terrace
- Child Friendly
Security/Safety
US $186/Night
7 Nights - US $1,300
Cabin
10.0(27 Reviews)
1 Bedroom
1 Bath
4 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
Air Conditioner
US $236/Night
7 Nights - US $1,654
House
9.6(7 Reviews)
3 Bedrooms
2 Baths
8 Guests
1280.91 ft²
- Parking
- Internet
Pet Friendly- Child Friendly
US $94/Night
7 Nights - US $658
Cabin
10.0(12 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
Spa- Balcony/Terrace
- Kitchen
US $416/Night
7 Nights - US $2,909
Villa
7.3(6 Reviews)
4 Bedrooms
1 Bath
7 Guests
10.76 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Child Friendly
US $62/Night
7 Nights - US $434
Cabin
10.0(5 Reviews)
2 Bedrooms
1 Bath
8 Guests
1200 ft²
- Parking
- Spa
- Balcony/Terrace
- Kitchen
US $388/Night
7 Nights - US $2,713
House
5 Bedrooms
2 Baths
12 Guests
2400.35 ft²
- Hot Tub
- Parking
- Internet
- Child Friendly
US $607/Night
7 Nights - US $4,249
Cottage
10.0(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $280/Night
7 Nights - US $1,960
Why Choose Rent By Owner for your Windsor Resorts?
What makes our Resorts special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Windsor
How to Book Your Windsor Resorts
What's our booking process?
Our platform allows you to browse a curated selection of resorts. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Windsor
Common Resorts Amenities
What amenities can you expect?
Our Resorts are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Windsor Resorts Frequently Asked Questions
1. What are the top Resorts in Windsor?
There are a lot of options in Windsor. If you plan on staying in the Windsor area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Resorts in Windsor:
- Lake it or Leave it! Lake House just one mile from Lake Cumberland Marina
- Nancy Kentucky 1800s log cabin
- Lake side Abode with a Spectacular year round View of the lake. 🌅
- Direct Lake Access from Our Home! Best Views on Lake.Sunrise and Sunset!
- Sandy Acres Cabins (Big Cabin) - by Galilean Home
- Cozy Ranch Home 1 Mile from CUMBERLAND POINT Boat Ramp. Owner Managed Property.
- Russell Springs Getaway, 10 Mi to Lake Cumberland!
- Sandy Acres Hobbit - Near Galilean Home - Liberty
- 🌞The Abundant Life on Lakeshore🌞 - Lakeview Home <1/4 Mile to Public Boat Ramp
- Cumberland Haven! One mile to Cumberland Point boat ramp and park.
2. How many Resorts are available in Windsor?
Currently, the total number of properties listed by RBO in 2026 is over 245 in the Windsor area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Windsor.
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8 Guests
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- Parking
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10.0(3 Reviews)
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10.0(2 Reviews)
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New
House
10.0(1 Review)
2 Bedrooms
1 Bath
8 Guests
1120 ft²
- Parking
- Balcony/Terrace
- Kitchen
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US $448/Night
7 Nights - US $3,139
House
10.0(1 Review)
2 Bedrooms
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6 Guests
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- Internet
US $272/Night
7 Nights - US $1,903
Cabin
9.8(50 Reviews)
1 Bedroom
1 Bath
6 Guests
726 ft²
- Hot Tub
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- Balcony/Terrace
- Kitchen
US $203/Night
7 Nights - US $1,420
Cabin
9.8(12 Reviews)
2 Bedrooms
2 Baths
8 Guests
1473 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $291/Night
7 Nights - US $2,037
Cabin
9.6(27 Reviews)
2 Bedrooms
1 Bath
6 Guests
896 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $203/Night
7 Nights - US $1,420
