Winchester holiday lettings

We found 871 holiday rentals — enter your dates for availability

Discover a selection of 14 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:25 Sept - 2 Oct

Image gallery for Charming Writer's Cottage in the Heart of Middleburg

Tavern - Office 2
9.8 out of 10, Exceptional, (165 reviews)
Exceptional
(165 reviews)

Charming Writer's Cottage in the Heart of Middleburg

Middleburg

16% off
Price is £1,427
for 7 nights, 1 cottage
£204 per night
includes taxes & fees
Charming Writer's Cottage in the Heart of Middleburg

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Why visit Winchester

  • Historical intrigue: Discover Winchester's rich history through its historic houses and landmarks, offering a fascinating glimpse into the past.
  • Outdoor adventures: Enjoy the scenic landscapes and picturesque lakes, perfect for hiking, picnicking, and family-friendly activities.
  • Charming neighbourhoods: Explore vibrant areas like Huntington Meadows, known for their welcoming atmosphere and beautiful surroundings.
  • Diverse accommodation: Choose from a variety of holiday rentals, including cosy cottages and spacious houses, tailored to your needs.
  • Cultural experiences: Engage with local colleges and universities to enrich your understanding of the city’s cultural fabric.

Popular types of accommodation in Winchester

Discover the charm of Winchester with our diverse selection of vacation rentals. Whether you prefer a private home, a cosy cottage, or a rustic cabin, we have an array of options to suit your needs. From spacious house rentals to comfortable apartment rentals, you'll find the perfect base for your adventures. Explore the historic city and enjoy a memorable stay in one of our lovely Winchester accommodations.

  • Houses: The top choice for visitors to Winchester, these homes offer a comfortable and spacious option for families or groups.
  • Cabins: A favourite among those seeking a rustic escape, cabins provide a delightful retreat in nature.
  • Cottages: Ideal for a quaint and homely stay, cottages are perfect for couples or small families.
  • Chalets: These charming lodgings offer a unique experience with a touch of alpine allure.
  • Apartments: A convenient option for those wanting self-catering facilities in the heart of the city.**

Top attractions in Winchester

Winchester, Virginia, offers a delightful blend of outdoor adventures and historical attractions, making it an ideal destination for culture-seekers and families alike. Visitors can explore historic houses, renowned colleges and universities, and picturesque lakes. For a truly enriching experience, be sure to delve into the rich history of Winchester, which promises to captivate all who venture there.

  • Shenandoah University: A historic institution located in the heart of Winchester, Shenandoah University offers a vibrant atmosphere filled with cultural events, arts performances, and historical significance. Explore its beautiful campus and enjoy the enriching educational environment.
  • Museum of the Shenandoah Valley: This art museum showcases an impressive collection of regional artwork and historical artefacts. Visitors can immerse themselves in the unique culture and history of the Shenandoah Valley through engaging exhibits and beautiful gardens.
  • Shenandoah Valley Discovery Museum: Perfect for families, this children's museum provides interactive exhibits that inspire curiosity and learning. It combines fun and education, making it an ideal spot for children to explore the rich culture of the region.

Things to do recommended for couples

For a romantic getaway in Winchester, Virginia, explore Valerie Hill Winery, just 5.6km away, known for its charming atmosphere. Alternatively, visit A-T Gift Company Farm Winery at 11.2km for outdoor delights, or Bluemont Vineyard, 15.6km distant, perfect for wine tasting amidst stunning views.

Things to do recommended for families

During your visit to Winchester, Virginia, families can unwind at Jim Barnett Park, enjoy activities at Appleland Sports Center, and let the kids play at Clearbrook Park Playground, all of which offer a delightful blend of wellness and relaxation just a short drive away.

Things to do recommended for groups

Groups visiting Winchester can enjoy a day of shopping at Apple Blossom Mall, challenge themselves at Rock Harbor Golf Course, or catch a show at Bright Box Theater, immersing themselves in local entertainment and culture.

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

If you’re planning a trip with a group, family, or pets, or if you’re considering longer stays, it's important to apply the right filters to suit your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Winchester with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Winchester with young kids: Travelling with young children can present its challenges. It’s essential to prioritise their comfort and safety, as well as ensure access to suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Winchester: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, take a look at Vrbo 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 perfect place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include features such as a parking space, a lovely kitchen, or a private pool in your search as well.

Where to stay in and around Winchester

Winchester, Virginia, is a charming city that offers a delightful blend of historical intrigue and natural beauty. Explore its picturesque streets, rich heritage, and vibrant urban atmosphere. Nearby cities and neighbourhoods, like Huntington Meadows, enhance the experience with family-friendly vibes and scenic landscapes, making it an ideal destination for outdoor adventures. Whether you're wandering through historic sites or enjoying the lush surroundings, Winchester promises a memorable holiday.

  • Stephenson: Situated approximately 3.1km from Winchester, Stephenson is a vibrant city that beckons adventure seekers and nature enthusiasts. Known for its stunning scenery and outdoor activities, visitors can enjoy a variety of recreational options, including motor racing at the local racetrack and exploring the nearby national state park. The picturesque lake adds to the charm, making it an ideal spot for a relaxing day out or an active weekend. Whether you're looking to unwind in nature or engage in thrilling adventures, Stephenson offers a delightful travel experience.
  • Kernstown: Nestled within the Winchester area, Kernstown is a charming village perfect for those eager to connect with the great outdoors. This locale features scenic hiking trails and excellent access to recreational areas, appealing to both casual walkers and avid hikers. The nearby national park and stunning waterfall provide breathtaking backdrops for a day of exploration. Kernstown's serene environment and inviting atmosphere make it an excellent choice for visitors looking to immerse themselves in nature and enjoy the beauty of the Virginia landscape.
  • Shawnee Land: Shawnee Land, another quaint village in the Winchester vicinity, invites tourists to experience its natural splendour and outdoor allure. The area is renowned for its recreational opportunities, with close proximity to both a national park and a serene lake. Visitors can engage in a variety of outdoor activities, from picnicking to hiking and fishing, all while soaking in the beautiful scenery. Shawnee Land offers a peaceful retreat for those wishing to escape the hustle and bustle, making it a perfect addition to your travel itinerary.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 HighSlightly High
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 SunnyAverageAverage

Booking with Vrbo is simple

Are you keen to save on your next getaway? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you could enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board provides you with a dedicated area to plan new adventures, pick up where you last stopped, or easily review and arrange your travel plans. You can now find the properties you've previously saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-gb/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:

  • 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)
  • Deer Lake (16.7 mi / 26.9 km)
  • Shenandoah Lake Beach (18.9 mi / 30.4 km)
  • Front Royal Entrance Shenandoah National Park (19.5 mi / 31.3 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.
How much does it cost to rent a holiday home in Winchester?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winchester to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winchester holiday house rentals?
You can find great discounts on house rentals in Winchester on Vrbo, 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.
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.
Can I find long-stay holiday rentals in Winchester?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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 Vrbo.
Are there any Winchester holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
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.
How early should I book a Winchester holiday rental?
Book your Winchester holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my Winchester home rental booking on Vrbo?
To find Winchester holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Winchester holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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