Windsor Cottage Rentals
Cottage
9.8(26 Reviews)
4 Bedrooms
2 Baths
8 Guests
Balcony/Terrace
Kitchen
Air Conditioner
Internet
CA $412/Night
7 Nights - CA $2,885
Cottage
5.0(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Kitchen
- Air Conditioner
- Internet
Child Friendly
CA $262/Night
7 Nights - CA $1,836
House
10.0(6 Reviews)
2 Bedrooms
1 Bath
6 Guests
Parking- Kitchen
- Air Conditioner
- Internet
CA $332/Night
7 Nights - CA $2,324
House
10.0(1 Review)
3 Bedrooms
2 Baths
12 Guests
150.69 ft²
Hot Tub- Parking
- Balcony/Terrace
- Air Conditioner
CA $593/Night
7 Nights - CA $4,154
CA $181/Night
7 Nights - CA $1,264
Apartment
9.8(24 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $193/Night
7 Nights - CA $1,352
House
6.5(4 Reviews)
6 Bedrooms
4 Baths
15 Guests
1047.69 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
CA $188/Night
7 Nights - CA $1,316
House
9.4(21 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $320/Night
7 Nights - CA $2,243
House
1 Bedroom
3 Baths
6 Guests
Oceanfront- Parking
Ocean View
View
CA $829/Night
7 Nights - CA $5,799
Apartment
8.6(14 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $216/Night
7 Nights - CA $1,509
House
3 Bedrooms
3 Baths
10 Guests
2497.23 ft²
- Hot Tub
- Parking
Pool- View
CA $597/Night
7 Nights - CA $4,182
Apartment
8.0(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $182/Night
7 Nights - CA $1,271
People Visiting Windsor Also Like
Why Choose Rent By Owner for your Windsor Cottage Rentals?
What makes our Cottage Rentals 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 Cottage Rentals
What's our booking process?
Our platform allows you to browse a curated selection of cottage rentals. 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 Cottage Rentals Amenities
What amenities can you expect?
Our Cottage Rentals 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
Frequently Asked Questions About Windsor Rental Cottages
1. What are the top Cottages 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 Cottages in Windsor:
- Paradise Found in Illinois
- Ultimate Country Home with a 4800 sq.ft shed- pickle ball, corn hole, and more!
- Binion Lodge: Wooded Privacy Near Lake Shelbyville
- Moose Cabin - Secluded 12 Acre Cabin w/Fishing Pond near Lake Shelbyville
- Spacious 5-bedroom Home Centrally Located-Sleeps 14!
- Cozy Refurbished Cottage Near Lake Shelbyville - Pet & Boat Friendly
- Country Living in Mattoon
- Cozy Country Home Near Lake Shelbyville
- The Little House on Prairie: Family-Friendly 2-Bedroom Getaway
- Quaint and colorful with fun amenities!
2. How many Cottages are available in Windsor?
Currently, the total number of properties listed by RBO in 2026 is over 2 in the Windsor area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Windsor.
More Rentals You May Like Near Windsor
House
2 Bedrooms
2 Baths
8 Guests
1851.39 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
CA $450/Night
7 Nights - CA $3,148
Cabin
1 Bedroom
1 Bath
4 Guests
- Balcony/Terrace
Pet Friendly- Child Friendly
Barbecue/Outdoor Cooking
CA $256/Night
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New
House
3 Bedrooms
3 Baths
8 Guests
2400.35 ft²
- Parking
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CA $404/Night
7 Nights - CA $2,827
New
House
4 Bedrooms
3 Baths
8 Guests
2400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $444/Night
7 Nights - CA $3,107
House
10.0(28 Reviews)
3 Bedrooms
2 Baths
12 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $692/Night
7 Nights - CA $4,842
House
10.0(7 Reviews)
5 Bedrooms
4 Baths
14 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $749/Night
7 Nights - CA $5,242
House
10.0(3 Reviews)
3 Bedrooms
1 Bath
6 Guests
1100 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $494/Night
7 Nights - CA $3,459
House
9.8(11 Reviews)
4 Bedrooms
3 Baths
12 Guests
2000 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $575/Night
7 Nights - CA $4,024
House
9.6(20 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
CA $401/Night
7 Nights - CA $2,810
Cabin
9.6(9 Reviews)
3 Bedrooms
2 Baths
11 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $579/Night
7 Nights - CA $4,051
Apartment
9.4(48 Reviews)
3 Bedrooms
1 Bath
6 Guests
1400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $238/Night
7 Nights - CA $1,665
House
9.4(32 Reviews)
3 Bedrooms
3 Baths
10 Guests
2500 ft²
Private Pool- Oceanfront
- Hot Tub
- Parking
CA $760/Night
7 Nights - CA $5,316
