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Greenwood vacation rentals

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Scroll through and select from vacation rentals in Greenwood to find one that's perfect for your trip. Whether you’re staying in a vacation home with friends, family, or even just your pets, you'll find the amenities you need and want, including parking and a TV. Whatever you're looking for, you'll be sure to find a rental for everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Greenwood

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Find out more about Greenwood

Why visit Greenwood

  • Outdoor Adventures: Greenwood is a haven for outdoor enthusiasts, offering activities like hiking and skiing amidst stunning natural scenery.
  • Cultural Exploration: Visitors can immerse themselves in the rich history of historic colleges and universities in the area.
  • Family-Friendly Excursions: The charming neighborhoods, like Swain Road, provide perfect spots for family outings and relaxation.
  • Diverse Accommodations: From cozy cabins to modern condos, Greenwood offers a variety of lodging options for a comfortable stay.
  • Scenic Trails: Experience picturesque hiking trails that showcase the area's breathtaking landscapes.

Popular types of accommodation in Greenwood

Planning a getaway to Greenwood? You're in for a treat. Discover a range of accommodation options, from cozy houses and charming cabins to modern condos. Whether you're searching for Greenwood apartments or rental properties in the area, you'll find the perfect place to relax and unwind. Explore your options for apartments in Greenwood and make your vacation truly memorable.

  • Houses: The most sought-after choice for visitors to Greenwood, offering spacious and comfortable living for families or groups.
  • Cabins: A favorite second option, these rustic getaways immerse you in nature, perfect for a peaceful retreat.
  • Condos: Ideal for those seeking modern amenities, condos provide a stylish and convenient stay.
  • Apartments: A practical choice, apartments offer the comforts of home in a variety of settings.
  • Cottages: These quaint and cozy accommodations add a touch of charm to your visit.**

Top attractions near Greenwood

Greenwood, Virginia, is an ideal destination for outdoor enthusiasts and adventure seekers, offering stunning scenery and rich cultural experiences. Visitors can explore a variety of attractions, including historic colleges and universities, ski resorts, and national and state parks. Whether you're seeking thrilling activities or a serene getaway, Greenwood caters to all types of travelers looking to immerse themselves in nature and history.

  • Blue Ridge Parkway North Entrance: A gateway to breathtaking mountain views, this visitor center offers outdoor activities perfect for families and adventurers alike, with trails that showcase the stunning beauty of the Blue Ridge Mountains.
  • University of Virginia: A UNESCO World Heritage site, this historic university features remarkable architecture and rich cultural heritage, inviting visitors to explore its beautiful campus and learn about its storied past.
  • Rockfish Gap Entrance Shenandoah: As a national park entrance, it provides access to unparalleled scenic vistas and thrilling outdoor adventures, including hiking and wildlife viewing amidst the stunning backdrop of the Shenandoah Valley.

Things to do recommended for couples

Welcome to Greenwood, Virginia. Enjoy a romantic day at King Family Vineyards, just 2 miles away, or Veritas Vineyard and Winery, 5 miles away. For adventure, head to Wintergreen Resort, 13 miles away, where you can ski together and take in stunning outdoor views.

Things to do recommended for families

Families visiting Greenwood, Virginia, can enjoy exciting sports experiences at Scott Stadium, Davenport Field, and Klockner Stadium, all located 14 miles away. These venues offer a vibrant atmosphere perfect for sports enthusiasts and family bonding, making for a memorable outing.

Things to do recommended for groups

Groups visiting Greenwood can enjoy local flavors at Starr Hill Brewery and Silverback Distillery, both featuring romantic and entertaining atmospheres. Don't miss a cultural experience at Wayne Theatre, perfect for family outings 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 Greenwood

If you’re traveling with a group, family, or pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful booking tips for Vrbo.

  • Traveling to Greenwood with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. The good news is that you can easily filter for all of these options and more on Vrbo.
  • Traveling to Greenwood with young kids: Traveling with young kids can be tricky. It's important to prioritize their comfort and safety, along with amenities that are suitable for their age, like a private swimming pool. Additionally, you should think about how close you are to attractions that are fun for the whole family.
  • Taking your pets with you to Greenwood: For many families, a vacation isn't truly complete without their furry companion. If that resonates with you, take a look at Vrbo listings that welcome pets. Most pet-friendly properties offer amenities like feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Greenwood: If you're seeking vacation rentals with discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly locate 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 as well.

Where to stay near Greenwood

Greenwood, Virginia, offers a delightful escape for outdoor enthusiasts and adventure seekers. Surrounded by stunning scenery, visitors can explore nearby neighborhoods and enjoy family-friendly excursions. The charming atmosphere of the area, including Swain Road, provides a perfect backdrop for urban adventures and relaxation. Whether you're hiking scenic trails or indulging in local culture, Greenwood is an ideal destination for creating unforgettable memories on your vacation.

  • Waynesboro: Located a mere 7 miles from Greenwood, Waynesboro is a charming city that attracts outdoor enthusiasts and adventure seekers alike. Visitors can enjoy a wealth of recreational activities in the surrounding area, including skiing at local ski fields. The stunning landscapes are perfect for exploration, with the nearby national park and state park offering breathtaking views and trails. Don’t miss a day at the local lake, where you can relax, fish, or partake in various water activities.
  • Afton: Just 4 miles from Greenwood, Afton is a haven for those who love outdoor adventures, particularly skiing. This vibrant city is renowned for its ski resorts and fields, making it an ideal destination during the winter months. Afton is surrounded by the natural beauty of the national park and state park, providing numerous opportunities for hiking and enjoying the great outdoors. The picturesque lake nearby is another highlight, offering a serene spot for picnicking and relaxation.
  • Crozet: Also located 4 miles from Greenwood, Crozet is a delightful city perfect for outdoor lovers and scenic explorers. The area features various recreational activities, including skiing and visiting ski fields. With its close proximity to the national park and state park, visitors can immerse themselves in nature's beauty through hiking and sightseeing. The nearby lake adds to Crozet's charm, offering a beautiful place to unwind and enjoy the tranquil surroundings.

Best time to go to Greenwood

If you're planning a trip to Greenwood, it's a good idea to check both the weather and property rates. The warmest months are July and July. Peak season runs in July, July to August, August, October and October, while off-peak times, like March, March to April, April, September and September tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January32.4°F (0.2°C)Light RainMostly SunnyAverageSlightly High
January32.4°F (0.2°C)Light RainMostly SunnyAverageSlightly High
February36.3°F (2.4°C)Light RainMostly SunnyAverageSlightly High
February36.3°F (2.4°C)Light RainMostly SunnyAverageSlightly High
March43.3°F (6.3°C)Light RainMostly SunnySlightly LowSlightly Low
March43.3°F (6.3°C)Light RainMostly SunnySlightly LowSlightly Low
April53.4°F (11.9°C)Light RainMostly SunnySlightly LowSlightly Low
April53.4°F (11.9°C)Light RainMostly SunnySlightly LowSlightly Low
May62.4°F (16.9°C)Light RainMostly SunnyAverageAverage
May62.4°F (16.9°C)Light RainMostly SunnyAverageAverage
June70.5°F (21.4°C)Light RainMostly SunnyAverageSlightly Low
June70.5°F (21.4°C)Light RainMostly SunnyAverageSlightly Low
July75.0°F (23.9°C)Light RainMostly SunnySlightly HighAverage
July75.0°F (23.9°C)Light RainMostly SunnySlightly HighAverage
August72.7°F (22.6°C)Light RainMostly SunnySlightly HighAverage
August72.7°F (22.6°C)Light RainMostly SunnySlightly HighAverage
September66.6°F (19.2°C)Light RainMostly SunnySlightly LowAverage
September66.6°F (19.2°C)Light RainMostly SunnySlightly LowAverage
October55.8°F (13.2°C)Light RainMostly SunnySlightly HighAverage
October55.8°F (13.2°C)Light RainMostly SunnySlightly HighAverage
November43.9°F (6.6°C)Light RainMostly SunnyAverageAverage
November43.9°F (6.6°C)Light RainMostly SunnyAverageAverage
December37.6°F (3.1°C)Light RainMostly SunnyAverageSlightly High
December37.6°F (3.1°C)Light RainMostly SunnyAverageSlightly High

Booking with Vrbo is simple

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that suits your budget, simply use our filters to sort by price, location, and the type of vacation rental you're interested in. We're here to help you find the perfect option.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform where you can easily create new trips, resume your previous planning, or organize your travel itinerary. You'll be able to find your saved or booked properties neatly categorized into Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Book a vacation rental for your Greenwood getaway

Enjoy the wineries and other features of Greenwood. This city has something for everyone. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Greenwood

Are you searching for attractions to see while you're in town? Venture out of your cozy vacation rental and check out everything that Greenwood has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • King Family Vineyards (2.4 mi / 3.8 km)
  • Veritas Vineyard and Winery (4.7 mi / 7.5 km)
  • Afton Mountain Vineyards (5.5 mi / 8.8 km)
  • Pippin Hill Farm & Vineyards (8.9 mi / 14.2 km)
  • Wintergreen Resort (13.2 mi / 21.2 km)
  • Trump Winery (16.8 mi / 27.1 km)

Exploring the natural landscape of Greenwood

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Greenwood is a great spot to appreciate mother nature. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Rockfish Gap Entrance Shenandoah (4.8 mi / 7.7 km)
  • Blue Ridge Parkway North Entrance (5 mi / 8 km)
  • Humpback Rocks (9.6 mi / 15.4 km)
  • Sherando Lake Recreation Area (16.1 mi / 25.9 km)
  • Carter Mountain Orchard (16.9 mi / 27.1 km)
  • Viette's Gardens (10.8 mi / 17.4 km)

How to get to and around Greenwood

Fly into Weyers Cave, VA (SHD-Shenandoah Valley Regional), the closest airport, located 16.1 mi (25.9 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Charlottesville-Albemarle Airport (CHO), which is 18.7 mi (30.1 km) away.

Frequently asked questions

What is the best area to stay in Greenwood, Virginia, United States of America when booking a vacation rental?
When considering a vacation rental in Greenwood, Virginia, the ideal area to stay would be near the scenic countryside, where you can enjoy the tranquility and natural beauty the region offers. This area is known for its charming rural atmosphere and proximity to outdoor activities. Nearby, you can explore stunning local attractions such as the beautiful hiking trails at the Blue Ridge Parkway, which provide breathtaking views and opportunities for outdoor adventures.

Additionally, the historic charm of nearby communities adds to the appeal, with quaint shops and local dining options that reflect the character of the region. The area is relatively small, with a handful of vacation rentals available, allowing for a more intimate and personalized experience.
How much does it cost to rent a vacation home in Greenwood?
Prices for vacation rentals in Greenwood 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 Greenwood 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 Greenwood vacation house rentals?
You can find great discounts on house rentals in Greenwood 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 Greenwood?
In Greenwood, vacation rentals primarily consist of cottages and vacation houses, with several of each type available throughout the area. These accommodations are often located in serene environments, providing a peaceful retreat for travelers. Most cottages feature cozy interiors with fully equipped kitchens, comfortable living spaces, and outdoor areas for enjoying the natural surroundings. Vacation houses typically offer more space, making them ideal for families or groups, with multiple bedrooms and larger living areas.
Are there any family house rentals in Greenwood?
In Greenwood, Virginia, there are several family-friendly house rentals available. Visitors can find charming homes located in this picturesque rural area, often featuring ample space for families to spread out. Many of these properties come equipped with full kitchens, allowing for easy meal preparation, and comfortable living areas superb for relaxation after a day of exploring.

The locale is close to various outdoor attractions, including hiking trails and scenic spots that are ideal for family outings. Additionally, nearby points of interest, such as local farms and vineyards, provide opportunities for great experiences and cultural immersion.
Can I find long-stay vacation rentals in Greenwood?
A long-stay vacation rental in Greenwood 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 any remote work vacation rentals in Greenwood?
In Greenwood, Virginia, there are several vacation rentals that cater to remote workers. These properties typically offer essential amenities such as high-speed Wi-Fi, dedicated workspaces, and sometimes even printers, making them ideal for those looking to balance work and leisure. Many rentals are set in peaceful surroundings, providing a tranquil atmosphere conducive to productivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Greenwood vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Greenwood 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 Greenwood?
In Greenwood, popular rental amenities cater to travelers seeking comfort and convenience. Most vacation rentals feature a deck or patio, allowing guests to enjoy the scenic outdoors while relaxing. Kitchens are commonly included, enabling visitors to prepare their own meals, and many properties come equipped with coffee and tea makers for that great morning brew. A desk is often available, providing a dedicated workspace for those who may need to catch up on tasks. Additionally, onsite parking is a standard amenity, making it easy for guests to explore the surrounding areas without hassle.
How early should I book a Greenwood vacation rental?
Book your Greenwood 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 Greenwood, Virginia, United States of America?
In Greenwood, Virginia, visitors can enjoy the charming rural atmosphere and outdoor activities. The area is known for its proximity to the Blue Ridge Mountains, making it an excellent base for hiking and exploring nature. The nearby Shenandoah National Park offers stunning views, diverse wildlife, and numerous trails for hiking enthusiasts.

The local wineries, such as those found along the Monticello Wine Trail, provide opportunities for tastings and tours, showcasing the region's burgeoning wine scene. Greenwood is also close to the historic town of Charlottesville, where travelers can visit attractions like Thomas Jefferson's Monticello and the vibrant Downtown Mall, known for its shops and restaurants.

For those interested in outdoor recreation, the South Fork of the Rivanna River offers opportunities for fishing, canoeing, and picnicking.
Can I change or cancel my Greenwood home rental booking on Vrbo?
To find Greenwood 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 Greenwood 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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