Winchester Cottage Rentals
Cottage
10.0(7 Reviews)
1 Bedroom
1 Bath
4 Guests
850 ft²
Hot Tub
Fireplace/Heating
Balcony/Terrace
Kitchen
R5,306/Night
7 Nights - R37,148
Cottage
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
Air Conditioner
Internet
R3,110/Night
7 Nights - R21,772
House
10.0(83 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Parking
R2,133/Night
7 Nights - R14,937
House
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
850.35 ft²
- Hot Tub
- Fireplace/Heating
- Parking
- Internet
R3,588/Night
7 Nights - R25,117
Bed & Breakfast
10.0(49 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R3,136/Night
7 Nights - R21,951
House
10.0(54 Reviews)
2 Bedrooms
1 Bath
4 Guests
950 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R2,111/Night
7 Nights - R14,775
Bed & Breakfast
9.8(67 Reviews)
1 Bedroom
1 Bath
2 Guests
172.22 ft²
Skiing- Fireplace/Heating
- Balcony/Terrace
View
R4,790/Night
7 Nights - R33,527
House
10.0(25 Reviews)
1 Bedroom
1 Bath
2 Guests
2000 ft²
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Kitchen
R5,031/Night
7 Nights - R35,216
House
9.5(108 Reviews)
3 Bedrooms
6 Baths
5 Guests
276.27 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
R2,075/Night
7 Nights - R14,531
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
2 Guests
725 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
R5,849/Night
7 Nights - R40,947
House
9.5(11 Reviews)
1 Bedroom
1 Bath
2 Guests
882.64 ft²
- Balcony/Terrace
- Parking
- Internet
Child Friendly
R1,802/Night
7 Nights - R12,615
House
9.8(94 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R3,378/Night
7 Nights - R23,639
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Why Choose Rent By Owner for your Winchester Cottage Rentals?
What makes our Cottage Rentals special?
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How to Book Your Winchester 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
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02
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03
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Explore and book the perfect rental in Winchester
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 Winchester Rental Cottages
1. What are the top Cottages in Winchester?
There are a lot of options in Winchester. If you plan on staying in the Winchester area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Cottages in Winchester:
- Sophisticated Bungalow, sparkling clean, walk to downtown, quiet neighborhood.
- Heavenly Bungalow, immaculately clean, close to downtown!
- Historical John Rast House
- Riverfront Log Cabin in Roseburg’s Wine Country
- Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
- Indigo Collective - Modern Comfort & Bold Design
- Holiday Inn Express And Suites Roseburg North By Ihg
- Charming 4-bedroom Pearce Historic Farmhouse in Roseburg with AC and WIFI
- Singing Waters at N. Umpqua
- Stylish Escape - Chic & Cozy with relaxing backyard
2. How many Cottages are available in Winchester?
Currently, the total number of properties listed by RBO in 2026 is over 2 in the Winchester area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Winchester.
More Rentals You May Like Near Winchester
House
8.9(21 Reviews)
2 Bedrooms
1 Bath
5 Guests
226.04 ft²
Spa- Fireplace/Heating
- Balcony/Terrace
- View
R3,821/Night
7 Nights - R26,741
House
9.8(21 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R6,901/Night
7 Nights - R48,302
R2,877/Night
7 Nights - R20,133
House
9.8(21 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
Pet Friendly- Kitchen
- Parking
R2,934/Night
7 Nights - R20,538
House
9.8(7 Reviews)
1 Bedroom
1 Bath
3 Guests
360 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R1,615/Night
7 Nights - R11,300
House
9.6(39 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R2,756/Night
7 Nights - R19,288
House
9.6(30 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R2,252/Night
7 Nights - R15,765
House
9.6(20 Reviews)
1 Bedroom
1 Bath
2 Guests
880 ft²
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
R2,267/Night
7 Nights - R15,862
House
9.4(19 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R1,837/Night
7 Nights - R12,859
Apartment
9.4(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R4,059/Night
7 Nights - R28,413
Apartment
1 Bedroom
1 Bath
2 Guests
854 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
R6,276/Night
7 Nights - R43,934
Cabin
10.0(29 Reviews)
5 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R8,742/Night
7 Nights - R61,193
