Winchester holiday rentals

We found 860 holiday rentals — enter your dates for availability
Discover a selection of 13 homes, 26 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.

Holiday rentals with weekly discounts – Winchester

Showing deals for:30 Oct - 6 Nov

Image gallery for Vinewood Estate | Luxury Vineyard Wellness Sanctuary

Everything you could want for a fun family or friend getaway! Multiple firepits, Lots of seating on the deck and around the pool.
10 out of 10, Exceptional, (58 reviews)
Exceptional
(58 reviews)

Vinewood Estate | Luxury Vineyard Wellness Sanctuary

Hillsboro

8% off
Price is AU$16,362
for 7 nights, 1 chalet
AU$2,337 per night
includes taxes & fees
Vinewood Estate | Luxury Vineyard Wellness Sanctuary

Find spaces that suit your style

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    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Winchester

  • Historic charm: Winchester boasts a rich cultural heritage, with historic houses and landmarks that tell the tale of its storied past.
  • Scenic beauty: Enjoy picturesque lakes and nearby parks, perfect for leisurely strolls and outdoor adventures.
  • Vibrant downtown: The city's bustling centre features historic architecture alongside modern boutiques and eateries.
  • Cultural immersion: Experience local arts through community theatres and museums that celebrate Winchester's traditions.
  • Convenience and comfort: A range of cosy, private lodgings ensure a memorable and hassle-free stay.

Popular types of accommodation in Winchester

Discover Winchester, Virginia, a charming city with a rich history and delightful attractions. Whether you’re exploring local landmarks or enjoying leisurely strolls in its scenic parks, our selection of private holiday homes, cabins, and cottages provides a comfortable stay. With options including hotels with parking, star accommodations, free wifi, and parking, your visit to Winchester promises convenience and a memorable experience.

  • Private Holiday Homes: The top choice for visitors seeking a home-away-from-home experience in Winchester, offering comfort and privacy.
  • Cabins: A delightful option for those wanting a rustic escape, often nestled in serene natural settings.
  • Cottages: Charming and quaint, these are perfect for a romantic getaway or a peaceful retreat.
  • Chalets: Ideal for those who appreciate a unique stay, combining cosy interiors with stunning views.
  • Apartments: A convenient choice for urban explorers, providing modern amenities in accessible locations.**

Top attractions in and around Winchester

Winchester, Virginia offers a delightful mix of historic houses, landmarks, and scenic lakes, perfect for family outings or adventurous explorations. The city's rich cultural heritage is complemented by outdoor activities and the charm of local attractions, including the Winchester Little Theatre. Whether you are in search of a cultural immersion or a breath of fresh countryside air, Winchester provides a memorable experience for all travellers.

  • Summit Point Motorsports Park: Thrilling motorRacing experience just 18km from Winchester, offering an adrenaline rush and adventure vibes.
  • Patsy Cline Historic House: A charming historicHouse in Winchester, providing cultural insights into local heritage and a cosy atmosphere.
  • Museum of the Shenandoah Valley: A captivating artMuseum within Winchester, showcasing regional art and cultural treasures in an inspiring setting.

Things to do recommended for couples

For a romantic getaway in Winchester, explore the charming Historic District with its quaint shops and cosy cafés. Enjoy a leisurely walk along the picturesque trails of the Shenandoah River and indulge in a wine tasting at local vineyards, creating memorable moments together in this enchanting setting.

Things to do recommended for families

Families visiting Winchester can explore the engaging interactive exhibits at the Museum of the Shenandoah Valley and enjoy a fun day at the Winchester Science Museum, where kids can participate in hands-on activities that inspire curiosity and learning.

Things to do recommended for groups

Experience the thrill of motorsport at Summit Point Motorsports Park, located 18km from Winchester. Enjoy adrenaline-pumping races and embrace the adventurous atmosphere with your group for an unforgettable day out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Winchester

When travelling with a group, family, or pets, or if you're seeking extended stays, it's essential to apply the appropriate filters that align with your priorities. Here are some helpful booking tips for Stayz.

  • Traveling to Winchester with a group: Think about how many bedrooms you require, along with amenities like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options and more on Stayz.
  • Traveling to Winchester with young kids: Travelling with young children can present its challenges. It’s essential to prioritise their comfort and safety, along with suitable amenities, such as a private swimming pool. Additionally, it’s wise to think about your closeness to attractions that are suitable for families.
  • Taking your pets with you to Winchester: For many, a family holiday feels incomplete without their beloved four-legged companion by their side. If this resonates with you, take a look at Stayz properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winchester: If you're seeking holiday rentals with discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Winchester

Winchester, Virginia, is a charming city steeped in history and nestled amidst picturesque scenery. Visitors can explore the vibrant downtown area, where historic architecture meets modern boutiques and eateries. The city's rich heritage is showcased through its landmarks and museums, while outdoor enthusiasts can enjoy nearby parks and trails. With a friendly atmosphere and a blend of urban and scenic vibes, Winchester offers a delightful escape for travellers seeking both adventure and relaxation.

  • Jordan Springs: This charming village lies a mere 8km from Winchester, offering travellers a delightful blend of outdoor pursuits and scenic vistas. Visitors can engage in adventure activities and explore a range of recreational areas, with a picturesque lake, national state park, and nature reserve nearby. Ideal for those who appreciate the outdoors, Jordan Springs provides a serene escape with opportunities to immerse in nature’s splendour.
  • Berryville: Situated 16km from Winchester, Berryville is a city that combines the allure of outdoor adventures with cultural experiences. Wander through recreational areas or enjoy a visit to the local shopping centre and educational attractions. The scenic backdrop is enhanced by a nearby lake and the presence of both a national state park and a national park. Berryville offers an engaging mix of natural beauty and community life, perfect for an enriching day out.
  • Millwood: Also located 16km from Winchester, Millwood presents a vibrant setting for those keen on outdoor activities. This city is well-known for its recreational areas and well-maintained golf courses, providing ample space for both leisurely and active pursuits. With a national state park, a local park, and a historic place enriching the vicinity, Millwood is a destination that offers a harmonious balance of nature and cultural heritage.

Best time to go to Winchester

If you're planning a trip to Winchester, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January31.3°F (-0.4°C)Light RainMostly SunnyModerately LowAverage
February34.7°F (1.5°C)Light RainMostly SunnyModerately LowSlightly Low
March42.3°F (5.7°C)Light RainMostly SunnyModerately LowSlightly Low
April52.9°F (11.6°C)Light RainMostly SunnyAverageSlightly Low
May62.4°F (16.9°C)Light RainMostly SunnyAverageAverage
June70.9°F (21.6°C)Light RainMostly SunnyModerately HighAverage
July75.9°F (24.4°C)Light RainMostly SunnyModerately HighSlightly High
August73.8°F (23.2°C)Light RainMostly SunnyModerately HighAverage
September66.9°F (19.4°C)Light RainMostly SunnyAverageAverage
October55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
November43.5°F (6.4°C)Light RainMostly SunnyAverageSlightly High
December36.7°F (2.6°C)Light RainMostly SunnyAverageSlightly High

Booking with Stayz is simple

Are you hoping to make your next getaway more affordable? Being flexible with your travel dates can be beneficial, as prices often fluctuate. You might also enjoy considerable savings by opting for a longer stay. To discover a Stayz property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz's innovative Trip Board provides you with a dedicated space to craft new trips, resume your previous journeys, or review and organise your plans. Properties you've saved or booked in the past can now be located under Potential, Upcoming, or Current Trips. To access your Trip Boards, please visit: https://www.stayz.com.au/trips

**Based on Vrbo properties bookings.

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)
  • Dinosaur Land (8.7 mi / 14 km)
  • Summit Point Motorsports Park (11.1 mi / 17.9 km)
  • Blue Ridge Shadows Golf Club (13.6 mi / 21.8 km)
  • Bluemont Vineyard (18.7 mi / 30.1 km)
  • Naked Mountain Winery & Vineyards (19.8 mi / 31.9 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:

  • Mackintosh Fruit Farm (6.6 mi / 10.6 km)
  • Lake Frederick Boat Launch (9.8 mi / 15.7 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.