Winchester holiday rentals

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Discover a selection of 21 homes, 22 apartments and other holiday rentals in Winchester that are perfect for your trip. Holiday homes offer the best amenities for you and your friends, family or even pets, such as parking and a fireplace. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that is 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

Why people love visiting historical Winchester

Enjoy the area's history, theatre scene and entertainment with a rental holiday home in Winchester. This city's skyscrapers, shopping and restaurants attract many visitors, as does its scenic and cosmopolitan location. 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 Winchester

Are you hoping to find attractions to visit in the city? Venture out of your cosy holiday rental and experience everything that makes Winchester a fun place to get away to. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Rock Harbor Golf Course (2.2 mi / 3.5 km)
  • Valerie Hill Winery (8.6 mi / 13.8 km)
  • Dinosaur Land (8.7 mi / 14 km)
  • Virginia River Trips (9.2 mi / 14.8 km)
  • Summit Point Motorsports Park (11.1 mi / 17.9 km)
  • Blue Ridge Shadows Golf Club (13.6 mi / 21.8 km)

Exploring the natural features in Winchester

Whether you're an active traveller or just want to appreciate the scenery, Winchester is a great place to get out in nature. These are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Jim Barnett Park (0.9 mi / 1.5 km)
  • Mackintosh Fruit Farm (6.6 mi / 10.6 km)
  • Shenandoah River (16.6 mi / 26.8 km)
  • Shenandoah Lake Beach (18.9 mi / 30.4 km)
  • Front Royal Entrance Shenandoah National Park (19.5 mi / 31.3 km)
  • Skyline Caverns (19.8 mi / 31.8 km)

How to get to and around Winchester

The nearest airport is in Martinsburg, WV (MRB-Eastern West Virginia Regional), located 18 mi (28.9 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Washington Dulles International Airport (IAD), which is 41.7 mi (67.1 km) away.

Frequently asked questions

What is the best area to stay in Winchester when booking a holiday home?
Gainesboro is one of the more popular locations where you’ll find a Stayz holiday home in Winchester. Have a look at our range of comfortable stays and then get ready to experience the best of this destination.
What is the most popular type of holiday home accommodation in Winchester?
Houses are the most popular style of holiday home in Winchester, according to our data. Even if you’ve got a different idea about what you want, Stayz has properties in a variety of shapes and sizes. Browse our options to find your perfect fit.
How much does it cost to rent a holiday home in Winchester?
The average price for a holiday home in Winchester depends on a number of factors, such as property type, length of stay and time of year. Whether you’re thinking about a villa with space for extended family or an apartment for just you and your sweetheart, just add your dates of travel to see some great-value stays.
How much does it cost to rent a beach house in Winchester?
The average price for a holiday home close to the beach in Winchester depends on when you’re going and the size and style of property you’re looking for. You can find prices quickly and easily on Stayz by entering your preferred travel dates and destination. Then use the filters to select the number of bedrooms and amenities important to you, such as a pool, WiFi and air conditioning.
Are there pet-friendly holiday homes in Winchester?
Good news! Yes. You can choose from four holiday homes that allow pets in Winchester. Many of our pet-friendly holiday homes even have an outdoor space for your four-legged friend to play in, doggie beds, complimentary treats and proximity to parks or green space. Apply the “Pets allowed” filter to find your pawfect holiday home on Stayz.
What are popular home amenities in Winchester?
Some of the most popular home amenities people look for in Winchester are a garden, a lake view and a fireplace. Whether you’re on a trip with family, pals or even pets, Stayz holiday homes include the best amenities for starting a new adventure with your loved ones.
Are there large group holiday homes in Winchester?
Take your pick of four Stayz holiday homes in Winchester that can accommodate a group of five or more guests. You’ll get all the privacy and space you need to chill out with your nearest and dearest — and nobody else.
Are there holiday homes in Winchester that welcome kids?
With four family-friendly holiday properties to select from in Winchester, now is a superb time to introduce your kids to the pleasures of travel. Check our “Properties good for families” filter to look for stays that feature amenities ideal for holidaying families, like multiple bedrooms, patios, entertainment units and bunk beds.
What are the top attractions for families in Winchester?
There are loads of fabulous things to see and do with the family in Winchester, including:

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

Can I find two-bedroom holiday homes in Winchester?
Winchester has two two-bedroom holiday homes that you can choose from. Discover a holiday home with all the privacy and space you need at a price you’ll love on Stayz.
Are there holiday homes with WiFi in Winchester?
You’ll find three holiday homes with WiFi in Winchester. If you’d like to disconnect from the world on your escape, but still want to be connected to the web, these getaways have just what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Winchester?
Winchester has four holiday homes where you can kick back in air-conditioned comfort. To locate a property on Stayz that comes with this amenity, enter your travel dates and use the convenient filters to select the “air conditioning” box.
How old do you have to be to rent a holiday home in Winchester?
You’ll need to check with the Winchester holiday home you’re looking at on Stayz as the age limit varies. However, it’s normally 16, 18 or 21.
How long can I rent a holiday home in Winchester for?
How long you can rent a holiday home in Winchester depends on the property. Simply enter your desired dates to see a list of options offering extended stays. With many features such as laundries and air conditioning, as well as some offering discounted weekly or monthly prices, you’re sure to find someplace just right to call your home away from home in Winchester.

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