Windsor Cottage Rentals
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
R2,714/Night
For 7 Nights R19,004
2002.09 ft²
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Parking
R1,047/Night
For 7 Nights R7,327
1 Bedroom
1 Bathroom
Family Friendly
Other
- Child Friendly
R7,145/Night
For 7 Nights R50,013
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
R2,257/Night
For 7 Nights R15,799
2002.09 ft²
9 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
R4,484/Night
For 7 Nights R31,385
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R2,790/Night
For 7 Nights R19,528
4004.17 ft²
24 Guests
7 Bedrooms
3 Bathrooms
House
- Fireplace/Heating
- Pet Friendly
- Parking
R5,593/Night
For 7 Nights R39,153
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
R2,714/Night
For 7 Nights R19,004
1194.79 ft²
6 Guests
2 Bedrooms
1 Bathroom
House
- Fireplace/Heating
- Pet Friendly
- Parking
R4,323/Night
For 7 Nights R30,256
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
R2,714/Night
For 7 Nights R19,004
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
Ski Chalet
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
R6,738/Night
For 7 Nights R47,167
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
R3,295/Night
For 7 Nights R23,060
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
Other Places to Stay in Windsor, OH
Windsor Mills Covered Bridge
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:
- Forever spring cabin
- Geauga Maple Cottage
- Little house on the farm
- Historic Century Home on Chardon Square
- The Thistle House off Chardon Square
- The Wildflower - Private cabin in wooded setting
- Farmhouse at Memory LakenSleeps 6 - 3 bedrooms - 1 bath
- Peaceful Country Retreat w/Firepit Near Venues & Private Setting.
- Nestled Inn Mespo Modern & Cozy Apartment
- The Horse & Harness BnB-Nestle by the Fire
2. How many Cottages are available in Windsor?
Currently, the total number of properties listed by RBO in 2026 is over 63 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
600 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
R3,058/Night
For 7 Nights R21,408
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
R3,058/Night
For 7 Nights R21,408
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
R2,714/Night
For 7 Nights R19,004
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R2,246/Night
For 7 Nights R15,717
850 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
R2,780/Night
For 7 Nights R19,462
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
R2,437/Night
For 7 Nights R17,058
2000 ft²
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R1,669/Night
For 7 Nights R11,677
8 Guests
1 Bedroom
1 Bathroom
Pet Friendly
RV Rental
- Pet Friendly
- Child Friendly
- Designated Smoking Area
R818/Night
For 7 Nights R5,724
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
R2,699/Night
For 7 Nights R18,890
1767 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R7,281/Night
For 7 Nights R50,962
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R4,247/Night
For 7 Nights R29,733
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Kitchen
- Parking
R3,393/Night
For 7 Nights R23,747
