Winchester house rentals

We found 696 house rentals — enter your dates for availability

  • Peace of mind

    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

Are there any holiday home rentals in Winchester?
Select one of our 696 holiday home rentals in Winchester and you'll have the ideal base for your next trip. Old Town Winchester, College Park and Kernstown are among the city's most sought-after neighbourhoods.
How much does it cost to stay in a holiday rental house in Winchester?
A number of factors will influence how much you pay for a holiday home rental in Winchester, such as the size of the property and when and how long you want to stay. All you have to do is key in your holiday dates and any preferences to find a house that works with your budget and taste.
When is the best time to rent a holiday house in Winchester?
The ideal time is whenever you can slip away from your everyday routine and enjoy the weather you prefer. For most Stayz guests searching for a holiday home rental in Winchester, Frederick County, that's August. Average daily temperatures during this month range from 17ºC to 29ºC.
Where can I rent a Winchester holiday house with great views?
Stayz has some excellent holiday home rentals in Winchester, including houses with views of historic areas. In between seeing the sights, unwind and stare at scenes that are an attraction in themselves.
Does Winchester have any weekend house rentals?
Some of Stayz's holiday houses can be rented just for the weekend, making them ideal for impulsive getaways. Enter your preferred travel dates to check out the availability. You may need to adjust the dates and have a little flexibility in your plans to find the right holiday home rental in Winchester.
Are there any pet-friendly house rentals in Winchester?
If you'd like to enjoy Winchester with your faithful friend at your side, use our handy filter tool to search for pet-friendly houses. Select the "Pets allowed" box to find a holiday home rental with welcome touches like dog toys and complimentary treats. After all, when the family takes a trip, the pets should tag along too!
What are the top things to do in Winchester?
It's no surprise why families love Winchester, with popular attractions like Summit Point Motorsports Park, Museum of the Shenandoah Valley and Apple Blossom Mall to explore. Check out this destination's wonders together and then return to the comforts of your holiday home rental.
Why should I book my holiday rental house with Stayz?
Booking your holiday home rental with Stayz means you'll have the whole place for your exclusive use — your own private retreat, without any distractions from other people. Also, our flexible payment and cancellation policies give you the freedom to amend your plans if necessary.