Winchester vacation rentals

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your current months are March, 2024 and April, 2024.
March 2024
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Discover a selection of 18 homes and other vacation rentals in Winchester that are perfect for your trip. Vacation homes provide the amenities you need and want for your stay with friends, family, or just your pet, including parking and a garden. At the end of the day, you'll be able to choose a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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Why people love visiting historic Winchester

Enjoy the area's history, theater scene and entertainment and make a vacation rental your home during your stay in Winchester. This city's skyscrapers, shopping and restaurants attract many visitors, and its scenic and cosmopolitan location add to the charm. With a vacation 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 looking for top things to see and do in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Winchester a fun place to get away. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Rock Harbor Golf Course (2.2 mi / 3.5 km)
  • Summit Point Motorsports Park (11.1 mi / 17.9 km)
  • Hollywood Casino at Charles Town Races (18.5 mi / 29.8 km)
  • Bluemont Vineyard (18.7 mi / 30.1 km)
  • Valerie Hill Winery (8.6 mi / 13.8 km)
  • Dinosaur Land (8.7 mi / 14 km)

Exploring the natural features in 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 features, all within 30 miles (48.2 km) of the city center:

  • Shenandoah River (16.6 mi / 26.8 km)
  • Sky Meadows State Park (17.7 mi / 28.5 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)
  • Dickey Ridge Visitor Center (21.8 mi / 35 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 center. If you can't find a flight that works for your travel itinerary, you can also fly into Washington Dulles Intl. 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 vacation rental?

Gainesboro is one of the more popular locations where you'll find a Vrbo vacation rental 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 vacation rental accommodation in Winchester?

Houses are the most popular style of vacation rental in Winchester, according to our data. Even if you've got a different idea about what you want, Vrbo 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 vacation rental in Winchester?

The average price for a vacation 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 vacation rental 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 Vrbo 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 vacation rentals in Winchester?

Good news! Yes. You can choose from four vacation rentals that allow pets in Winchester. Many of our pet-friendly vacation rentals 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 vacation home on Vrbo.

What are popular rental amenities in Winchester?

Some of the most popular rental 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, Vrbo vacation homes include the best amenities for starting a new adventure with your loved ones.

Are there large group vacation rentals in Winchester?

Take your pick of four Vrbo vacation 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 vacation rentals in Winchester that welcome kids?

With four family-friendly vacation 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 vacationing 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 vacation rentals in Winchester?

Winchester has two two-bedroom vacation rentals that you can choose from. Discover a vacation home with all the privacy and space you need at a price you'll love on Vrbo.

Are there vacation rentals with WiFi in Winchester?

You'll find three vacation rentals 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 Vrbo.

How can I find vacation rentals with air conditioning in Winchester?

Winchester has four vacation rentals where you can kick back in air-conditioned comfort. To locate a property on Vrbo that comes with this amenity, enter your travel dates and use the convenient filters to select the "air conditioning" box.

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