Winchester holiday rentals

We found 2 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Winchester that are perfect for your trip. Whether you're staying in a holiday rental with friends, family or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include parking and a fireplace. You'll be able to choose a property to rent that has what everyone needs, including options that are accessible or non-smoking.

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

Book a holiday rental for your Winchester getaway

Learn about the unique charm of Winchester with a stay in a holiday home rental. This city has something for everyone. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in and around Winchester

Are you hoping to find top things to see and do in the area? Venture out of your cosy holiday rental and check out everything that makes Winchester a fun spot to go on holiday. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Smokie Ridge Vineyard (10.3 mi / 16.5 km)
  • Rideau Glen Golf Club (15.9 mi / 25.6 km)
  • Domaine du Cervin (7.5 mi / 12.1 km)
  • Sandy Mountain Golf Course (9.9 mi / 16 km)
  • Poplar Grove Golf Club (16.3 mi / 26.2 km)

Exploring the natural landscape of Winchester

Whether you're an outdoor enthusiast or just want to take in the scenery, Winchester is a great place to spend some time outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Rideau River Provincial Park (15.7 mi / 25.3 km)
  • Rideau Canal (26.8 mi / 43.2 km)
  • Mountain Memorial Community Park (8.2 mi / 13.2 km)
  • Ferguson Forest Dog Park (15 mi / 24.2 km)
  • Russell Township Dog Park (12.2 mi / 19.7 km)
  • Gideon Adams Park (13.1 mi / 21.1 km)

Travelling to and around Winchester

The nearest airport is in Ottawa International Airport (YOW), located 22.1 mi (35.6 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Massena, NY (MSS-Massena Intl.), which is 27.2 mi (43.8 km) away.

Frequently asked questions

How much does it cost to rent a holiday home in Winchester?
A range of things influence how much you pay for a holiday home in Winchester, like the type of property, season and length of stay. Still, all of our holiday homes have something in common — amazing value. Just enter your travel dates to find your perfect match.
How much does it cost to rent a beach house in Winchester?
Prices for beach houses in Winchester 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 the number of guests to view your holiday home options and prices. From there you can use the filters to narrow your search by ratings, amenities and more.
How old do you have to be to rent a holiday home in Winchester?
The age limit can vary across properties on Stayz, so double-check the rules of the holiday home in Winchester you want to book. But usually, it’s 16, 18 or 21.
How long can I rent a holiday home in Winchester for?
The amount of time you can book a Winchester holiday home for depends on each property. Just tap in your travel dates to find available options offering longer term stays. They feature the things you need to make your extended break more convenient and comfortable, like kitchens and laundries. Some properties may also offer weekly or monthly discounts, so you can stick around for longer for less.