Old Town Winchester holiday rentals

We found 18 holiday rentals — enter your dates for availability

Discover a selection of 8 apartments and other holiday rentals in Old Town Winchester that are perfect for your trip. Holiday rentals provide the best amenities for your family, friends or furry companion, such as parking and a TV. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • 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

How much does it cost to rent a holiday home in Old Town Winchester?
Several factors can determine how much you’ll pay for a holiday home in Old Town Winchester, including the type of property, season and length of stay. However, all Stayz homes have something in common — excellent value. Just add your travel dates to find your ideal escape.
How much does it cost to rent a beach house in Old Town Winchester?
Prices for beach houses in Old Town Winchester may vary depending on the type and size of the property and when you plan to travel. Simply enter your dates of travel into Stayz and how many guests to view available options and prices. From there you can use our filter tool to refine your search by ratings, amenities, nearby activities and more.
What are the top attractions for families in Old Town Winchester?
Keep the kids happy at these fantastic family-friendly attractions in Old Town Winchester:

  • Shenandoah Valley Discovery Museum
  • Museum of the Shenandoah Valley
  • Jim Barnett Park

How old do you have to be to rent a holiday home in Old Town Winchester?
The minimum age requirements can differ across properties on Stayz, so double-check the rules of the holiday home in Old Town Winchester you want. But typically, it’s 16, 18 or 21.
How long can I rent a holiday home in Old Town Winchester for?
It’s up to the Old Town Winchester property. To browse a list of options offering extended stays, simply type your travel dates and number of guests into Stayz’s search page. Look forward to having the property to yourself, along with the comforts of home like a fully-equipped kitchen, air conditioning and a yard where the kids can play. Keep your eyes peeled for any long-term stays that offer weekly or monthly discounts.