Windsor Vacation Rentals & Ski-in/Ski-out Homes
Cabin
- Kentucky
- ·
- Russell Springs
- 2.64 mi to center
10.0Exceptional
(30 Reviews)
1 Bedroom
1 Bath
2 Guests
900 ft²
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $301/Night
7 Nights - US $2,107
House
10.0Exceptional
(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
- Kentucky
- ·
- Russell Springs
- 2.34 mi to center
1 Bedroom
1 Bath
Oceanfront- Parking
Ocean View- Balcony/Terrace
US $274/Night
7 Nights - US $1,918
Cabin
- Kentucky
- ·
- Russell Springs
- 6.78 mi to center
10.0Exceptional
(30 Reviews)
2 Bedrooms
1 Bath
6 Guests
760 ft²
- Parking
- Ocean View
- Balcony/Terrace
View
US $191/Night
7 Nights - US $1,335
House
- Kentucky
- ·
- Russell Springs
- 2.44 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
1001.04 ft²
- Parking
- Balcony/Terrace
Security/Safety
Business Services
US $153/Night
7 Nights - US $1,073
Cabin
- Kentucky
- ·
- Russell Springs
- 3.21 mi to center
10.0Exceptional
(12 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
Spa- Balcony/Terrace
- Kitchen
US $416/Night
7 Nights - US $2,909
Cabin
10.0Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
8 Guests
1200 ft²
- Parking
- Spa
- Balcony/Terrace
- Kitchen
US $388/Night
7 Nights - US $2,713
Cottage
- Kentucky
- ·
- Russell Springs
- 0.88 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $261/Night
7 Nights - US $1,829
Cabin
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
7 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $262/Night
7 Nights - US $1,837
Luxury Places to Stay in Windsor
Over 230+ Luxury Places to Stay in or Near Windsor
House
4 Bedrooms
2 Baths
14 Guests
2023.62 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $1,535/Night
7 Nights - US $10,747
House
4 Bedrooms
2 Baths
13 Guests
2023.62 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $1,194/Night
7 Nights - US $8,356
House
4 Bedrooms
2 Baths
14 Guests
2023.62 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $1,126/Night
7 Nights - US $7,880
New
House
4 Bedrooms
2 Baths
20 Guests
2023.62 ft²
- Parking
- Air Conditioner
- Internet
Pet Friendly
US $969/Night
7 Nights - US $6,786
House
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
16 Guests
2028 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $967/Night
7 Nights - US $6,767
House
4 Bedrooms
2 Baths
18 Guests
2028 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $933/Night
7 Nights - US $6,534
House
2 Bedrooms
1 Bath
8 Guests
1119.45 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $831/Night
7 Nights - US $5,815
House
4 Bedrooms
2 Baths
18 Guests
2023.62 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $825/Night
7 Nights - US $5,775
New
House
4 Bedrooms
2 Baths
22 Guests
2023.62 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $788/Night
7 Nights - US $5,517
Top-Rated Vacation Rentals with a Pool in Windsor
Over 3+ Top-Rated Vacation Rentals with a Pool in or Near Windsor
House
9.6Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
1800 ft²
Private Pool- Parking
Pool- Balcony/Terrace
US $325/Night
7 Nights - US $2,278
House
8.4Excellent
(8 Reviews)
5 Bedrooms
2 Baths
18 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $506/Night
7 Nights - US $3,542
House
4.9Average
(70 Reviews)
5 Bedrooms
5 Baths
10 Guests
4500 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $495/Night
7 Nights - US $3,465
Pet-Friendly Vacation Rentals in Windsor
Over 89+ Pet-Friendly Vacation Rentals in or Near Windsor
House
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
8 Guests
1120 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $463/Night
7 Nights - US $3,242
House
9.6Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
8 Guests
1280.91 ft²
- Parking
- Internet
- Pet Friendly
- Child Friendly
US $94/Night
7 Nights - US $658
House
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
8 Guests
1120 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $423/Night
7 Nights - US $2,961
House
4 Bedrooms
2 Baths
8 Guests
1496.18 ft²
- Parking
- Pet Friendly
- Child Friendly
- Security/Safety
US $312/Night
7 Nights - US $2,182
House
9.8Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
6 Guests
495 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $278/Night
7 Nights - US $1,946
Cabin
9.4Exceptional
(41 Reviews)
1 Bedroom
1 Bath
4 Guests
364 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $184/Night
7 Nights - US $1,286
Cabin
9.0Exceptional
(16 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $225/Night
7 Nights - US $1,578
House
- Kentucky
- ·
- Russell Springs
- 6.70 mi to center
1 Bedroom
4 Baths
12 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $672/Night
7 Nights - US $4,706
House
2 Bedrooms
2 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $510/Night
7 Nights - US $3,573
Large Vacation Homes & Villas in Windsor
Over 95+ Large Vacation Homes & Villas in or Near Windsor
House
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
10 Guests
1120 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $468/Night
7 Nights - US $3,276
Villa
- Kentucky
- ·
- Russell Springs
- 4.26 mi to center
7.3Very Good
(6 Reviews)
4 Bedrooms
1 Bath
7 Guests
10.76 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
Barbecue/Outdoor Cooking
US $62/Night
7 Nights - US $434
House
- Kentucky
- ·
- Russell Springs
- 6.78 mi to center
4 Bedrooms
3 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $699/Night
7 Nights - US $4,892
Cabin
9.6Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
10 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $265/Night
7 Nights - US $1,855
New
House
7.0Very Good
(1 Review)
4 Bedrooms
2 Baths
16 Guests
2023.62 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $787/Night
7 Nights - US $5,509
New
House
2 Bedrooms
1 Bath
10 Guests
1120 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $607/Night
7 Nights - US $4,251
House
2 Bedrooms
1 Bath
10 Guests
1120 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $509/Night
7 Nights - US $3,562
House
2 Bedrooms
1 Bath
10 Guests
1120 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $488/Night
7 Nights - US $3,419
New
House
2 Bedrooms
1 Bath
10 Guests
1020 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $468/Night
7 Nights - US $3,276
Wheelchair Accessible Vacation Homes in Windsor
Over 1+ Wheelchair Accessible Vacation Homes in or Near Windsor
Hotel
- Kentucky
- ·
- Russell Springs
- 1.81 mi to center
5.8Average
(97 Reviews)
4 Baths
150.69 ft²
Breakfast- Parking
- Internet
- Pet Friendly
US $80/Night
7 Nights - US $560
Windsor Resorts and Airbnb Homes Under $200
Over 51+ Windsor Resorts and Airbnb Homes Under $200
Cabin
- Kentucky
- ·
- Russell Springs
- 6.78 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
780 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $191/Night
7 Nights - US $1,340
House
2 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $89/Night
7 Nights - US $624
Cottage
1 Bedroom
1 Bath
- Child Friendly
US $80/Night
7 Nights - US $560
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Air Conditioner
- Internet
- Child Friendly
- Security/Safety
US $178/Night
7 Nights - US $1,246
Cabin
- Kentucky
- ·
- Russell Springs
- 6.78 mi to center
9.6Exceptional
(27 Reviews)
2 Bedrooms
1 Bath
6 Guests
896 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $200/Night
7 Nights - US $1,399
Cabin
- Kentucky
- ·
- Russell Springs
- 6.78 mi to center
8.0Excellent
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
758 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $191/Night
7 Nights - US $1,340
House
- Kentucky
- ·
- Russell Springs
- 3.18 mi to center
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $187/Night
7 Nights - US $1,312
Apartment
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
4 Guests
768 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $192/Night
7 Nights - US $1,343
Cabin
9.6Exceptional
(10 Reviews)
3 Bedrooms
2 Baths
8 Guests
1280 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $180/Night
7 Nights - US $1,262
Instantly Bookable Vacation Homes in Windsor
Over 108+ Instantly Bookable Vacation Homes in or Near Windsor
House
- Kentucky
- ·
- Russell Springs
- 3.37 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $208/Night
7 Nights - US $1,453
Cabin
- Kentucky
- ·
- Russell Springs
- 6.78 mi to center
9.8Exceptional
(50 Reviews)
1 Bedroom
1 Bath
6 Guests
726 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $202/Night
7 Nights - US $1,417
Cabin
9.8Exceptional
(13 Reviews)
2 Bedrooms
2 Baths
8 Guests
1473 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $261/Night
7 Nights - US $1,829
Cabin
- Kentucky
- ·
- Russell Springs
- 6.74 mi to center
9.6Exceptional
(20 Reviews)
2 Bedrooms
1 Bath
6 Guests
896 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $205/Night
7 Nights - US $1,438
Cabin
- Kentucky
- ·
- Russell Springs
- 6.78 mi to center
9.6Exceptional
(20 Reviews)
2 Bedrooms
1 Bath
6 Guests
896 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $205/Night
7 Nights - US $1,438
House
- Kentucky
- ·
- Russell Springs
- 2.44 mi to center
9.6Exceptional
(7 Reviews)
1 Bedroom
1 Bath
2 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $280/Night
7 Nights - US $1,960
Cottage
- Kentucky
- ·
- Bethelridge
- 3.02 mi to center
8.0Excellent
(1 Review)
1 Bedroom
2 Baths
2 Guests
1100 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $306/Night
7 Nights - US $2,145
House
2 Bedrooms
1 Bath
8 Guests
1120 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $468/Night
7 Nights - US $3,276
New
House
2 Bedrooms
1 Bath
8 Guests
1120 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $468/Night
7 Nights - US $3,276
Book a Last Minute Place to Stay in Windsor
About Windsor Vacation Rentals
Explore over 239 vacation rentals in Windsor with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Windsor for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Windsor. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Windsor tailored to your preferences. On average, these rentals offer 945.65 ft² of space, and are priced at an average of US $386 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Windsor at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
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Top Types of Ski Accommodations in Windsor
| Type | Count |
|---|---|
| Vacation Homes | 162 |
| Cabin Rentals | 44 |
| Unique Vacation Rentals | 12 |
| Cottages | 9 |
| Unique Vacation Rentals | 3 |
| Holiday Apartments | 2 |
| Others | 2 |
| B&B | 1 |
| Villas | 1 |
Use these Quick Filters to Find a Vacation Rental in Windsor
★ Pro Tip: Discover Your Ideal Vacation Rental in Windsor with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
Weather in Windsor, KY
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 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Frequently Asked Questions About Windsor?
What are the top vacation rentals in Windsor?
When organizing your trip to Windsor, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Windsor. Peruse our collection of highly-rated properties and secure your reservation today.
- Lake it or Leave it! Lake House just one mile from Lake Cumberland Marina
- Nancy Kentucky 1800s log cabin
- 🤩 Charming Lake Side Retreat perched above scenic Faubush Creek.
- Direct Lake Access from Our Home! Best Views on Lake.Sunrise and Sunset!
- Beautiful cabin nestled in the woods surrounded by water
- 2 Bedroom Family Cabin #3 3/4 Miles to Cumberland Marina WIFI-NO CLEANING FEE!
- Cozy Ranch Home 1 Mile from CUMBERLAND POINT Boat Ramp. Owner Managed Property.
- Sandy Acres Hobbit - Near Galilean Home - Liberty
- Russell Springs Getaway, 10 Mi to Lake Cumberland!
- 🌞The Abundant Life on Lakeshore🌞 - Lakeview Home <1/4 Mile to Public Boat Ramp
Which vacation homes or resorts in Windsor are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Windsor. Enjoy great views, locations and save money with SunSki Resorts.™
- Retreat house upper floor w/2 bedrooms in fabulous Nancy with cool AC breeze
- Secluded Jamestown Home about 5 Mi to Lake Cumberland!
- Laker Inn
How many SunSkiResorts vacation rentals or resorts are available in Windsor?
Discover the ideal vacation rental in Windsor with SunSki Resorts™. We provide an extensive selection of over 239 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Windsor.
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