Winchester Cottage Rentals
House
10.0(81 Reviews)
7 Bedrooms
5 Baths
24 Guests
6900 ft²
Private Pool
Hot Tub
Breakfast
Parking
US $5,496/Night
7 Nights - US $38,473
Hotel
8.4(182 Reviews)
6 Baths
303.18 ft²
- Private Pool
- Breakfast
- Parking
Pool
US $118/Night
7 Nights - US $823
US $108/Night
7 Nights - US $753
House
10.0(52 Reviews)
3 Bedrooms
3 Baths
10 Guests
2000 ft²
- Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $289/Night
7 Nights - US $2,023
Hotel
8.1(251 Reviews)
1 Bath
333.68 ft²
- Private Pool
- Parking
- Pool
- Air Conditioner
US $75/Night
7 Nights - US $525
Cabin
3 Bedrooms
2 Baths
8 Guests
- Parking
- Kitchen
- Air Conditioner
Internet
US $292/Night
7 Nights - US $2,045
Hotel
7.9(103 Reviews)
1 Bath
495.14 ft²
- Private Pool
- Parking
- Pool
- Air Conditioner
US $98/Night
7 Nights - US $685
Cabin
3 Bedrooms
2 Baths
8 Guests
- Balcony/Terrace
- Air Conditioner
- Internet
Child Friendly
US $272/Night
7 Nights - US $1,903
Hotel
7.5(177 Reviews)
1 Bath
290.63 ft²
- Private Pool
Oceanfront- Parking
- Pool
US $94/Night
7 Nights - US $655
Cabin
3 Bedrooms
2 Baths
8 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
US $221/Night
7 Nights - US $1,550
Hotel
7.2(116 Reviews)
5 Baths
290.63 ft²
- Parking
- Air Conditioner
- Internet
Pet Friendly
US $59/Night
7 Nights - US $411
House
3 Bedrooms
2 Baths
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $127/Night
7 Nights - US $891
Why Choose Rent By Owner for your Winchester 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 Winchester
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
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 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
Winchester Cottage Rentals Frequently Asked Questions
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:
- Sleep Inn & Suites South Jacksonville
- Hampton Inn Jacksonville
- Super 8 by Wyndham Jacksonville
- Quality Inn Jacksonville near I-72
- Holiday Inn Express Hotel & Suites Jacksonville by IHG
- Jacksonville Inn & Suites
- Knights Inn Jacksonville East Morton Ave
- Knights Inn Jacksonville
- Monroe Street Suites
- Villa DeWolf
2. How many Cottages are available in Winchester?
Currently, the total number of properties listed by RBO in 2026 is over 39 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
Hotel
6.9(30 Reviews)
5 Baths
247.57 ft²
- Breakfast
- Parking
- Air Conditioner
- Internet
US $140/Night
7 Nights - US $980
House
10.0(62 Reviews)
3 Bedrooms
2 Baths
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $217/Night
7 Nights - US $1,522
Cabin
10.0(20 Reviews)
1 Bedroom
1 Bath
2 Guests
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- Parking
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US $126/Night
7 Nights - US $883
Cabin
10.0(15 Reviews)
2 Bedrooms
1 Bath
8 Guests
900 ft²
- Parking
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US $158/Night
7 Nights - US $1,105
Cabin
9.8(67 Reviews)
1 Bedroom
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6 Guests
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- Parking
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US $139/Night
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New
House
3 Bedrooms
1 Bath
11 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $272/Night
7 Nights - US $1,907
Cabin
10.0(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $198/Night
7 Nights - US $1,383
House
10.0(26 Reviews)
3 Bedrooms
1 Bath
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $238/Night
7 Nights - US $1,669
Cabin
10.0(10 Reviews)
6 Bedrooms
4 Baths
21 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $205/Night
7 Nights - US $1,435
House
9.8(22 Reviews)
2 Bedrooms
2 Baths
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $135/Night
7 Nights - US $945
Apartment
9.6(5 Reviews)
2 Bedrooms
1 Bath
7 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $108/Night
7 Nights - US $756
House
4.5(2 Reviews)
2 Bedrooms
3 Baths
17 Guests
- Kitchen
- Air Conditioner
- Child Friendly
Wheelchair Accessible
US $575/Night
7 Nights - US $4,025
