Winchester vacation rentals

We found 848 vacation rentals — enter your dates for availability

Discover a selection of 13 homes, 27 apartments, 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.

Holiday rentals with weekly discounts - Winchester

Showing deals for:Aug 21 - Aug 28

Image gallery for Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More

Bedroom #1 with queen bed and full bathroom
10 out of 10, Exceptional, (20 reviews)
Exceptional
(20 reviews)

Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More

Bluemont

8% off
Price is $443
$3,098 for 7 nights
All fees included
Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More

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Find out more about Winchester

Why visit Winchester

  • Rich History: Discover historic houses and notable sites that showcase Winchester's fascinating past.
  • Outdoor Adventures: Enjoy the stunning scenery with family-friendly activities in the surrounding counties.
  • Charming Downtown: Explore the vibrant streets of Old Town, filled with local shops and culture.
  • Diverse Accommodations: Choose from cozy vacation rentals, including cabins and cottages for a unique stay.
  • Local Culture: Experience genuine hospitality and local events on E Whitlock Ave.

Popular types of accommodation in Winchester

Discover the charm of Winchester with a variety of vacation rentals to suit your needs. From cozy houses and inviting cabins to quaint cottages, you'll find the perfect spot for your getaway. Whether you're looking for single-family homes, spacious bedroom apartments, or a comfortable bedroom home, our platform offers transparency and savings to ensure you have a stress-free experience. Explore your options and make unforgettable memories in beautiful Winchester.

  • Houses: The top choice for visitors to Winchester, these homes offer spacious accommodations ideal for families or groups.
  • Cabins: A favorite for those seeking a rustic experience, cabins provide a peaceful escape in nature.
  • Cottages: These delightful small homes are perfect for a charming and cozy getaway.
  • Chalets: Offering a unique stay, chalets blend comfort with a mountain lodge feel.
  • Apartments: A convenient option, apartments provide all the essentials for a comfortable stay.**

Top attractions in Winchester

Winchester, Virginia, is a fantastic destination for outdoor and adventure enthusiasts, offering stunning scenery and a rich historical backdrop. Visitors can explore various attractions, including historic houses, scenic lakes, and notable historic sites. Whether you're seeking cultural experiences or family-friendly activities, Winchester has something for everyone, making it an ideal spot for a memorable vacation.

  • Shenandoah University: Experience the vibrant culture and history of this historic institution. Take a stroll through the picturesque campus and appreciate the blend of academic excellence with beautiful architecture.
  • Museum of the Shenandoah Valley: Explore captivating art exhibits and local history in this renowned museum. The stunning gardens and seasonal events enhance the cultural experience for visitors of all ages.
  • Shenandoah Valley Discovery Museum: A fun-filled destination for families, this interactive museum offers hands-on exhibits that engage children in learning about science, art, and the environment.

Things to do recommended for couples

For a romantic getaway in Winchester, visit Valerie Hill Winery, just 9 miles away, for a cozy vibe. A-T Gift Company Farm Winery, 18 miles out, offers outdoor charm, while Bluemont Vineyard, located 19 miles away, provides a picturesque setting for wine tasting and relaxation.

Things to do recommended for families

Your family will love exploring Jim Barnett Park for its recreational activities, or take a short trip to Clearbrook Park and Appleland Sports Center, both offering wellness vibes and fun experiences just a few miles from Winchester.

Things to do recommended for groups

Groups visiting Winchester can shop at the Apple Blossom Mall for a vibrant experience, enjoy a round of golf at Rock Harbor Golf Course amidst beautiful outdoor scenery, and catch a show at the Bright Box Theater for a taste of local culture and entertainment.

*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

No matter if you're traveling with friends, family, pets, or planning an extended stay, be sure to set your filters according to your top priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Winchester with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Winchester with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with 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 families, a vacation isn’t truly a vacation without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most 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 searching for vacation rentals that offer discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Winchester

Winchester, Virginia, offers a delightful blend of history, scenery, and urban charm. Explore the vibrant downtown and the quaint streets of Old Town, where history comes alive. The surrounding counties provide a family-friendly atmosphere perfect for outdoor adventures. Don’t miss E Whitlock Ave, an excellent location to experience local culture and hospitality. Whether you're seeking adventure or a relaxing getaway, Winchester has something special for every traveler.

  • Old Town Winchester: Nestled in the heart of Winchester, Old Town Winchester is a charming neighborhood that invites visitors to explore its rich history and vibrant culture. Known for its outdoor activities, family-friendly atmosphere, and adventurous spirit, this area offers a delightful blend of recreational spaces and shopping experiences. Stroll through the picturesque streets to discover local parks, the historic college university, and the nearby national state park, making it an ideal spot for both relaxation and exploration.
  • Stephenson: Located a mere 5 miles from Winchester, Stephenson is a city that boasts stunning scenery and exciting outdoor adventures. This area is perfect for thrill-seekers and nature lovers alike, with access to recreational areas and a renowned racetrack. Visitors can enjoy motor racing events or spend a day at the nearby lake, which is perfect for picnicking and water activities. Stephenson’s blend of adventure and natural beauty makes it a must-visit destination for those looking to soak in the great outdoors.
  • Winchester Historic District: The Winchester Historic District is a captivating neighborhood that showcases the area's rich heritage while providing plenty of family-oriented activities. Here, you can enjoy a round of golf at one of the local golf courses or indulge in shopping at charming boutiques. With a welcoming visitor center and beautiful parks nearby, this district invites you to step back in time while enjoying modern amenities. Its proximity to the national park adds an additional layer of outdoor adventure and exploration for visitors of all ages.

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 HighAverage
September66.9°F (19.4°C)Light RainMostly SunnyAverageAverage
October55.8°F (13.2°C)Light RainMostly SunnyAverageSlightly High
November43.5°F (6.4°C)Light RainMostly SunnyAverageSlightly High
December36.7°F (2.6°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board is a fantastic tool designed to help you plan your travels with ease. It offers a dedicated space to create new trips, pick up right where you left off, and view or organize your travel plans. You can easily find the properties you've saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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)
  • Dinosaur Land (8.7 mi / 14 km)
  • Summit Point Motorsports Park (11.1 mi / 17.9 km)
  • Bluemont Vineyard (18.7 mi / 30.1 km)
  • Delaplane Cellars (20.3 mi / 32.7 km)
  • Linden Vineyards (21.6 mi / 34.7 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:

  • Lake Frederick Boat Launch (9.8 mi / 15.7 km)
  • Cedar Creek and Belle Grove National Historical Park (13.4 mi / 21.6 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 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, Virginia, United States of America when booking a vacation rental?
A great area to consider when booking a vacation rental in Winchester, Virginia, is the Old Town district. This charming neighborhood is known for its beautifully preserved historic architecture and vibrant setting. One of the top attractions in Old Town is the Museum of the Shenandoah Valley, which offers fascinating exhibits on local history and art, as well as stunning gardens to explore. Additionally, the area is home to various boutique shops, cozy cafes, and restaurants, making it an ideal spot for enjoying local cuisine and shopping.

Another excellent option is the area around the Shenandoah University, which provides a lively environment with access to cultural events and performances throughout the year. This part of Winchester is also close to outdoor activities, with nearby parks and trails for hiking and enjoying nature. The number of vacation rental properties in these neighborhoods tends to be robust, offering a range of options from charming historic homes to modern apartments, ensuring that visitors can find accommodations that suit their preferences.
How much does it cost to rent a vacation home in Winchester?
Prices for vacation 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 vacation 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 vacation rental accomodation in Winchester?
In Winchester, apartments are the most popular vacation rental option, with about 23 available across the city. These apartments are typically located in convenient areas, providing easy access to local attractions and dining options. Most units come with fully equipped kitchens, cozy living spaces, and amenities like Wi-Fi and laundry facilities, making them a comfortable choice for travelers.

In addition to apartments, there are around 11 vacation houses available, which offer larger living spaces suitable for families or groups. These homes often feature multiple bedrooms, private yards, and full kitchens, allowing guests to enjoy a more private and spacious stay. Additionally, there are several cabins in the area, providing a rustic experience for those looking to immerse themselves in nature.
Are there any family house rentals in Winchester?
In Winchester, Virginia, there are several family-friendly vacation rentals available, with around 15 options to choose from. The area showcases a mix of charming homes situated in neighborhoods that provide easy access to local parks and historical sites. Many of these properties come equipped with spacious living areas, full kitchens ideal for preparing family meals, and outdoor spaces where children can play safely. Amenities such as Wi-Fi and air conditioning enhance comfort during your stay.

Visitors can explore the nearby Old Town Winchester, known for its vibrant shops, dining options, and historical landmarks like the Museum of the Shenandoah Valley. Additionally, the surrounding countryside offers opportunities for outdoor activities, including hiking and picnicking, ensuring that families have a memorable and enjoyable experience in this picturesque locale.
Can I rent a vacation home with a pool or hot tub in Winchester?
In Winchester, Virginia, several vacation homes are available for rent that feature pools and hot tubs. This charming city, known for its rich history and beautiful landscapes, offers a variety of properties that cater to travelers seeking relaxation. Many of these rentals come equipped with private pools, hot tubs, and spacious outdoor areas, ideal for enjoying the serene surroundings. Additionally, you can expect amenities like fully equipped kitchens, comfortable living spaces, and sometimes even game rooms, making them great for family gatherings or group getaways.
Can I find long-stay vacation rentals in Winchester?
A long-stay vacation rental in Winchester is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Winchester?
In Winchester, travelers can find a variety of pet-friendly house rentals, with around 16 options available. Many of these homes offer spacious layouts, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups traveling with pets. Some properties may even feature outdoor spaces such as fenced yards or patios, providing a safe environment for pets to enjoy the fresh air.

The city is surrounded by beautiful parks and natural areas that are superb for outdoor activities with pets. Nearby, the Jim Barnett Park offers walking trails, open fields, and picnic areas, creating an excellent setting for leisurely strolls or playtime with furry companions. Additionally, the historic downtown area provides pet-friendly cafes and shops, enhancing the overall experience for those traveling with pets. See all pet-friendly rentals in Winchester.
Are there any remote work vacation rentals in Winchester?
In Winchester, Virginia, there are numerous vacation rentals suitable for remote work, with about 29 options available. Many properties are equipped with essential amenities to support a productive work environment, including free Wi-Fi, dedicated desks, and comfortable chairs. Travelers can expect a variety of accommodations that provide a quiet atmosphere conducive to work, while also offering the comforts of home.

The historic downtown area of Winchester features charming properties close to local cafes and shops, allowing for easy breaks during the workday. Additionally, rentals may include amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces, enhancing the overall experience for those balancing work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winchester vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winchester with parking available—perfect for families or travelers 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 vacation rental amenities include onsite parking, which provides convenience for guests traveling by car. Most rentals come equipped with kitchens, allowing travelers to prepare their own meals and enjoy the comforts of home. Additionally, a coffee and tea maker is a common feature, superb for those who appreciate a warm beverage in the morning. Many properties are also pet-friendly, accommodating travelers who wish to bring their furry companions along. Finally, service animals are permitted, ensuring that guests with specific needs are well taken care of.
How early should I book a Winchester vacation rental?
Book your Winchester vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Winchester, Virginia, United States of America?
In Winchester, Virginia, visitors can explore a range of attractions that highlight the area's rich history and natural beauty. The Old Town district features charming 18th-century architecture, quaint shops, and restaurants, making it a delightful place to stroll and soak in the local atmosphere. Here, the historic Museum of the Shenandoah Valley offers insights into the region's past and beautiful gardens for leisurely walks.

For those interested in Civil War history, the Winchester National Cemetery and the nearby Cedar Creek and Belle Grove National Historical Park provide significant landmarks and educational opportunities about the battles that took place in the area.

Nature enthusiasts can venture to the scenic Shenandoah National Park, which is just a short drive away and offers hiking trails, breathtaking views, and outdoor activities. The area around the park is dotted with vacation rentals that allow travelers to enjoy both comfort and easy access to these natural wonders.

Additionally, the annual Apple Blossom Festival in May attracts visitors with its lively parade, music, and various family-friendly events, showcasing the community spirit of Winchester.
Can I change or cancel my Winchester home rental booking on Vrbo?
To find Winchester vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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