Windsor Holiday Rentals
Cabin
- Kentucky
- ·
- Russell Springs
- 6.78 mi to center
10.0Exceptional
(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
10.0Exceptional
(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
- 6.82 mi to center
10.0Exceptional
(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
- Kentucky
- ·
- Russell Springs
- 2.44 mi to center
10.0Exceptional
(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
- Kentucky
- ·
- Russell Springs
- 2.64 mi to center
10.0Exceptional
(27 Reviews)
1 Bedroom
1 Bath
4 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
Air Conditioner
US $236/Night
7 Nights - US $1,654
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
(5 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 $280/Night
7 Nights - US $1,960
Luxury Holiday Rentals in Windsor
Over 233+ Luxury Holiday Rentals in or Near Windsor
New
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
1 Bedroom
2 Baths
13 Guests
2023.62 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $1,194/Night
7 Nights - US $8,356
New
House
4 Bedrooms
2 Baths
14 Guests
2023.62 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Air Conditioner
US $1,126/Night
7 Nights - US $7,880
New
House
1 Bedroom
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
22 Guests
2023.62 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $1,114/Night
7 Nights - US $7,798
New
House
1 Bedroom
2 Baths
12 Guests
2023.62 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $1,111/Night
7 Nights - US $7,779
New
House
4 Bedrooms
2 Baths
20 Guests
2028 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,100/Night
7 Nights - US $7,697
New
House
4 Bedrooms
2 Baths
20 Guests
2028 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,035/Night
7 Nights - US $7,248
New
House
4 Bedrooms
2 Baths
12 Guests
2028 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $976/Night
7 Nights - US $6,829
Top-Rated Holiday Rentals with a Pool in Windsor
Over 3+ The Best Private Villas and Holiday Rentals in Windsor with a Pool
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 Holiday Rentals in Windsor
Over 91+ Pet-Friendly Holiday Rentals in or Near Windsor
House
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
495 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $252/Night
7 Nights - US $1,767
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
Cabin
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
7 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $260/Night
7 Nights - US $1,821
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
New
House
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
8 Guests
1120 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $448/Night
7 Nights - US $3,139
Cabin
9.4Exceptional
(41 Reviews)
1 Bedroom
1 Bath
4 Guests
364 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $191/Night
7 Nights - US $1,334
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
New
House
2 Bedrooms
1 Bath
8 Guests
1120 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $829/Night
7 Nights - US $5,804
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
Large Holiday Rentals and Private Villas in Windsor
Over 95+ Large Holiday Rentals and Private Villas in or Near Windsor
Cabin
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
10 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $261/Night
7 Nights - US $1,824
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
- Child Friendly
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
House
2 Bedrooms
1 Bath
10 Guests
1120 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $787/Night
7 Nights - US $5,512
House
5 Bedrooms
2 Baths
12 Guests
2400.35 ft²
- Hot Tub
- Parking
- Internet
- Child Friendly
US $607/Night
7 Nights - US $4,249
New
House
2 Bedrooms
1 Bath
10 Guests
1020 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $558/Night
7 Nights - US $3,904
House
2 Bedrooms
2 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $510/Night
7 Nights - US $3,573
House
2 Bedrooms
1 Bath
10 Guests
1120 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $471/Night
7 Nights - US $3,297
House
2 Bedrooms
1 Bath
10 Guests
1120 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $471/Night
7 Nights - US $3,297
Wheelchair Accessible Holiday Homes in Windsor
Over 1+ Wheelchair Accessible Holiday 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 Private Villas and Holiday Homes Under $200
Over 53+ Windsor Private Villas and Holiday Homes Under $200
House
- Kentucky
- ·
- Russell Springs
- 2.60 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $138/Night
7 Nights - US $968
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
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 $189/Night
7 Nights - US $1,322
Cabin
- Kentucky
- ·
- Russell Springs
- 6.78 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
758 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $189/Night
7 Nights - US $1,322
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 $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 $189/Night
7 Nights - US $1,325
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
House
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
9 Guests
1344 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $158/Night
7 Nights - US $1,107
Instantly Bookable Holiday Homes in Windsor
Over 109+ Instantly Bookable Holiday Homes in or Near Windsor
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 $203/Night
7 Nights - US $1,420
Cabin
9.8Exceptional
(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
- 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 $203/Night
7 Nights - US $1,420
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 $203/Night
7 Nights - US $1,420
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 $278/Night
7 Nights - US $1,946
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 $302/Night
7 Nights - US $2,114
New
House
2 Bedrooms
1 Bath
10 Guests
1120 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $471/Night
7 Nights - US $3,297
New
House
2 Bedrooms
1 Bath
10 Guests
1120 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $471/Night
7 Nights - US $3,297
House
2 Bedrooms
1 Bath
10 Guests
1120 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $414/Night
7 Nights - US $2,898
Book a Last Minute Place to Stay in Windsor
About Casai's Private Villas and Holiday Rentals in Windsor
Discover more than 242 vacation rentals available in Windsor. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Windsor.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Windsor, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Windsor. On average, places to stay near Windsor offer 951.12 ft², with nightly prices averaging US $399.
With Casai, finding and comparing holiday rentals in Windsor is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Windsor
| Type | Count |
|---|---|
| Vacation Homes | 161 |
| Cottages | 9 |
| Holiday Apartments | 2 |
| Villas | 1 |
Use these Quick Filters to Find a Holiday Rental in Windsor
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Windsor.
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 holiday rentals in Windsor?
With numerous options available in Windsor, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals 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. 🌅
- Americana Jacuzzi Lake View family Cabin3/4 mile to marina WIFI- NO CLEANING FEE
- Americana Hot Tub Cabin @ LakePointe Resort - no cleaning fees!
- Direct Lake Access from Our Home! Best Views on Lake.Sunrise and Sunset!
- Beautiful cabin nestled in the woods surrounded by water
- 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!
Which holiday homes in Windsor are best for families?
If you're searching for a family-friendly holiday home in Windsor, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Windsor:
- Retreat house upper floor w/2 bedrooms in fabulous Nancy with cool AC breeze
- Wake House - One of a Kind Floating Home on Lake Cumberland - Boat Slip - Boat Ramp Access - Sleeps 20
- Laker Inn
How many Casai.nz holiday rentals are available in Windsor?
As of 2026, Casai boasts over 242 properties listed in the Windsor area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Windsor.
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