Winchester cottage rentals

We found 69 cottage rentals — enter your dates for availability

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    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to stay in a cottage rental in Winchester?
Fancy or basic, in a busy tourist area or off the beaten track, peak season or shoulder season — these factors and more will influence how much your cottage rental in Winchester will cost. The length of your stay can also affect the overall price. Some properties offer discounts for longer stays, so be on the lookout for special offers.
When is the best time to rent a cottage in Winchester?
It all comes down to your budget, your weather preferences and if you prefer the buzz of peak season or a more relaxed vibe. Located in Frederick County, August is the most popular time to visit Winchester, with the average temperatures ranging between 17ºC and 29ºC. Have a look at the availability of our cottage rentals throughout the year and then make your choice.
Where can I rent a Winchester holiday cottage with great views?
With wonderful scenery just beyond your doorstep and many of the comforts of home, our cottage rentals are ideal places to kick back. Stayz has a variety of cottages in Winchester that feature views of historic areas, so make sure you have plenty of space on your camera roll.
Does Winchester have any lakeside cottages?
Wake up to lovely vistas every morning and drift off to the tranquil sounds of nature at night in one of Stayz's lakeside cottage rentals. Throw in some outdoor activities during the daytime and you've got yourself the ideal getaway by the water. To find out if there are any lakeside cottages in Winchester, use our "Location" filter and then select "Lake."
What are the top things to do in Winchester?
Get your Winchester getaway off to a flying start by heading to popular sights like Summit Point Motorsports Park, Museum of the Shenandoah Valley and Apple Blossom Mall. Stay in a Stayz cottage rental with the family and then discover the best of this destination together.
Why should I book my holiday cottage with Stayz?
When you opt for a Stayz cottage rental, the only people you have to share your living space with are those you bring along. It'll only be you, your closest companions and the entire place for your exclusive use. Our flexible cancellation policies also mean you can book your cottage with peace of mind if your plans change.