Winchester holiday rentals

We found 882 holiday rentals — enter your dates for availability
Discover a selection of 15 homes, 23 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:29 Jan - 5 Feb

Image gallery for Gruner Bungalow at Tranquility Farm & Winery

Sunroom
9.8 out of 10, Exceptional, (110 reviews)
Exceptional
(110 reviews)

Gruner Bungalow at Tranquility Farm & Winery

Purcellville

8% off
Price is AU$17,898
for 7 nights, 1 home
AU$2,557 per night
includes taxes & fees
Gruner Bungalow at Tranquility Farm & Winery

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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:

  • 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)
  • Dickey Ridge Visitor Center (21.8 mi / 35 km)
  • Cacapon Resort State Park (23.6 mi / 37.9 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 rental?
When considering a holiday rental in Winchester, Virginia, the historic Old Town area is one of the best choices. This charming neighbourhood is rich in history, characterised by its beautifully preserved 18th and 19th-century architecture. Visitors can enjoy a leisurely stroll along the quaint streets, exploring an array of boutique shops, cafés, and restaurants. A standout attraction in Old Town is the Museum of the Shenandoah Valley, which offers fascinating insights into the region's history, art, and natural beauty.

Another appealing area is the nearby Valley Avenue, which is known for its convenient access to various amenities and shopping options. This area is particularly popular among families and those looking for a more suburban feel while still being close to the city centre. Here, you can enjoy easy access to outdoor activities, including the scenic trails at the nearby Shenandoah National Park, making it an excellent choice for nature enthusiasts.

Overall, Winchester has a diverse range of properties available for holiday rentals, suiting different preferences and budgets.
What is the most popular type of holiday rental accomodation in Winchester?
In Winchester, apartments are the most popular type of holiday rental, with approximately 92 available throughout the city. These apartments are typically situated in convenient locations, providing easy access to local attractions such as the Old Town and the historic Winchester National Cemetery. Most units come equipped with modern amenities, including fully equipped kitchens, comfortable living spaces, and often laundry facilities, making them ideal for both short and extended stays.

For those seeking more space, around 44 holiday houses are also available, offering multiple bedrooms and outdoor areas, great for families or groups. Some properties may include features like private gardens or patios, allowing guests to enjoy the charming Virginia scenery. Additionally, there are several cabins in the area, providing a rustic retreat for nature lovers wanting to explore the surrounding countryside.
Are there any family house rentals in Winchester?
In Winchester, Virginia, there are several family-friendly house rentals available, with around 15 options to choose from. The area is known for its rich history and beautiful surroundings, making it an excellent choice for families. Many of these homes offer spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where children can play safely.

Visitors can explore the charming Old Town, which features quaint shops, local restaurants, and historical sites such as the Museum of the Shenandoah Valley. Additionally, the region is close to various parks and outdoor activities, providing ample opportunities for family outings.
Can I rent a holiday home with a pool or hot tub in Winchester?
In Winchester, there are several holiday homes available for rent that feature pools and hot tubs. This charming city, steeped in history, offers a variety of neighbourhoods where travellers can find these amenities. Many properties are located in tranquil residential areas, providing a peaceful retreat while still being close to local attractions.

Expect to find amenities such as private swimming pools, relaxing hot tubs, spacious outdoor patios, and fully equipped kitchens, making these homes ideal for families or groups seeking comfort and leisure during their stay. Some rentals may also offer additional features like outdoor dining spaces and gardens, superb for enjoying the pleasant Virginia weather.
Are there pet-friendly house rentals in Winchester?
In Winchester, there are several pet-friendly house rentals available, providing a great option for travellers looking to bring their furry companions along. Many of these properties are equipped with amenities such as spacious outdoor areas, modern kitchens, and comfortable living spaces that cater to families or groups.

The historic district of Winchester offers charming homes with easy access to local shops and restaurants, making it convenient for guests to explore the area while enjoying the company of their pets. Additionally, nearby parks such as Jim Barnett Park feature walking trails and open spaces where pets can roam and play, ideal for pet owners.
Are there any remote work holiday rentals in Winchester?
In Winchester, Virginia, there are numerous holiday rentals suitable for remote work, with around 116 options available. Many of these properties cater specifically to those looking to balance work and leisure, offering amenities such as high-speed internet, comfortable desks and chairs, and free Wi-Fi in the rooms.

Travellers can expect a range of accommodations, from cosy apartments in the historical downtown area to larger family homes on the outskirts. The downtown region is particularly appealing due to its proximity to local cafes and restaurants, providing ideal spots for a change of scenery during breaks. Additionally, Winchester is known for its rich history, with nearby attractions such as the Museum of the Shenandoah Valley and the historic Old Town, which also offer opportunities for relaxation after a productive day. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Winchester?
In Winchester, popular holiday rental amenities typically include onsite parking, which is a convenient feature for those travelling by car. Most properties come equipped with a kitchen, allowing guests to prepare their own meals and enjoy a home-like experience during their stay. Additionally, many rentals offer a coffee or tea maker, great for a morning pick-me-up. For pet owners, it's worth noting that several accommodations permit pets, making it easier for travellers to bring their furry companions along. Service animals are also welcome in these rentals, ensuring that guests with specific needs are well accommodated.
When is the best time to visit Winchester for a holiday rental?
The best time to visit Winchester for a holiday rental is during the peak season from July to September. This period attracts a vibrant mix of tourists keen to explore the area's rich history, stunning landscapes, and charming downtown. With warm temperatures averaging between 20 and 30 degrees Celsius, the summer months are great for outdoor activities such as hiking the nearby Appalachian Trail and visiting local vineyards.

July stands out as the most popular month, bustling with events and festivals that celebrate the region's heritage. Visitors can enjoy the lively option, take part in community activities, and explore historic sites like the Museum of the Shenandoah Valley, which offers a fascinating glimpse into the area's past.

For those seeking a more budget-friendly experience, November is an excellent choice. This quieter month allows for a more relaxed exploration of Winchester, with fewer crowds and the opportunity to appreciate the serene beauty of autumn as the leaves change colours. The mild weather during this time, usually ranging from 5 to 15 degrees Celsius, makes it comfortable for walking tours and visiting local shops.

Ultimately, whether you prefer the energetic buzz of the summer or the tranquil charm of the fall, Winchester offers a welcoming experience at any time of year.
What are the top attractions in Winchester?
In Winchester, Virginia, visitors can explore a range of attractions that highlight the city's rich history and natural beauty. The historic Old Town area is a must-visit, featuring beautifully preserved 18th and 19th-century buildings, charming boutiques, and local eateries. Key sites include the Old Court House Civil War Museum and the Handley Regional Library, both of which reflect the city's historical significance.

The Museum of the Shenandoah Valley offers a delightful combination of art, history, and beautiful gardens, making it a great spot for both education and relaxation. Nearby, the Winchester National Cemetery provides a solemn yet beautiful tribute to those who served in the military.

For nature enthusiasts, the surrounding Shenandoah Valley offers stunning landscapes and outdoor activities. The nearby Cedar Creek and Belle Grove National Historical Park provide opportunities for hiking and exploring the scenic countryside, while the Shenandoah River allows for kayaking and fishing adventures.
Are all fees included in the Winchester holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Winchester holiday homes with parking?
Stayz offers a wide selection of holiday homes in Winchester with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Winchester holiday homes?
You can find great discounts on holiday homes in Winchester on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Winchester holiday home booking on Stayz?
To find Winchester holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Winchester?
A long-stay holiday home in Winchester is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Winchester holiday home?
Book your Winchester holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Winchester?
Prices for holiday homes in Winchester vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Winchester to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.