Photo by Karyn Leary

Greenwood vacation rentals

We found 284 vacation rentals — enter your dates for availability

Nestled amidst the breathtaking landscapes of Lake Greenwood, this enchanting destination invites you to immerse yourself in outdoor adventures, historic charm, and vibrant neighborhoods. Whether you're hiking scenic trails, teeing off at local golf courses, or exploring the rich heritage at Swannanoa Palace, Greenwood offers something for everyone. With a variety of accommodations from cozy cabins to spacious homes, you'll find the perfect base to create lasting memories with family and friends while enjoying all the comforts of home.

Holiday rentals with weekly discounts - Greenwood

Showing deals for:Jan 1 - Jan 8

Interior
Pool
Private kitchen
Property grounds
Exceptional
(113 reviews)

Farm House on Working Vineyard Near Blue Ridge Mountains, Charlottesville

Afton

5% off
$670
$4,691 for 7 nights
All fees included
Farm House on Working Vineyard Near Blue Ridge Mountains, Charlottesville
Private kitchen
Private kitchen
Exterior detail
Interior
Exceptional
(62 reviews)

Rockfish Farmhouse - Home In the heart of The Rockfish Valley

Afton

9% off
$312
$2,185 for 7 nights
All fees included
Rockfish Farmhouse - Home In the heart of The Rockfish Valley
Pool & House at night
Kitchen showing dishwasher, sink area, and refrigerator, range & table
Front hall looking toward the front entry door
Living room with French doors open to the pool and mountains beyond
Exceptional
(7 reviews)

Heated Pool, Hot Tub, panoramic mountain views, near Vineyards + UVA

Crozet

9% off
$758
$5,308 for 7 nights
All fees included
Heated Pool, Hot Tub, panoramic mountain views, near Vineyards + UVA
A view of the North and rear from Stagecoach Road - pre-2022 metal roof
Interior
Living area
Dual sinks, quiet appliances, quartz counters, convection range, laundry closet.
Exceptional
(166 reviews)

Afton Station Cottage -Beautifully Renovated Blue Ridge Scenic Historic Setting

Afton

9% off
$259
$1,811 for 7 nights
All fees included
Afton Station Cottage -Beautifully Renovated Blue Ridge Scenic Historic Setting
Dining
Great mountain views, with relaxing pond.
Private kitchen
Room
Exceptional
(67 reviews)

Suite in Shenandoah Valley

Waynesboro

7% off
$163
$1,144 for 7 nights
All fees included
Suite in Shenandoah Valley
Living area
Afton Cabin Firepit
Afton Cabin Front
Living area
Exceptional
(28 reviews)

Afton Escape! NEW Arcade, Wineries, Breweries

Afton

8% off
$638
$4,467 for 7 nights
All fees included
Afton Escape! NEW Arcade, Wineries, Breweries
Exterior
Outdoor dining
Dining
Private kitchen
Exceptional
(8 reviews)

Perfect getaway at foothills of the Blue Ridge Mountains, with gorgeous views!

Afton

9% off
$290
$2,031 for 7 nights
All fees included
Perfect getaway at foothills of the Blue Ridge Mountains, with gorgeous views!
living room
Lots of natural light in this super cute kitchen with new granite countertops.
Master has it's own small deck with entrance front the french doors.
kitchen bar between kitchen and dining room
Exceptional
(53 reviews)

Coin Cottage farmhouse on 151 Trail in Nelson County

Afton

9% off
$308
$2,154 for 7 nights
All fees included
Coin Cottage farmhouse on 151 Trail in Nelson County
Private kitchen
Dining
Property grounds
Room
Wonderful
(12 reviews)

The Hawksbill Haus (w/ hot tub)

Waynesboro

9% off
$243
$1,703 for 7 nights
All fees included
The Hawksbill Haus (w/ hot tub)
Room
Exterior
Dining
4 person table with lots of natural light
Exceptional
(26 reviews)

Oasis on 151 • Hot Tub • Pool Table • Huge Home

Faber

18% off
$741
$5,190 for 7 nights
All fees included
Oasis on 151 • Hot Tub • Pool Table • Huge Home
Room
Exterior
Private kitchen
Living area
Exceptional
(10 reviews)

Cute Place 2yrs old near 2 Ski resorts, Many Wineries/Breweries, BR Parkway, .

Waynesboro

18% off
$145
$1,017 for 7 nights
All fees included
Cute Place 2yrs old near 2 Ski resorts, Many Wineries/Breweries, BR Parkway, .
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

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)
  • Sherando Lake Recreation Area (16.1 mi / 25.9 km)
  • Carter Mountain Orchard (16.9 mi / 27.1 km)
  • Humpback Rocks (9.6 mi / 15.4 km)
  • Doyles River Falls (13.4 mi / 21.6 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 are the best areas to stay in a vacation rental in Greenwood?
Greenwood offers a selection of vacation rentals that provide a private and comfortable base for your trip. These properties, primarily houses and cottages, are spread throughout the area, giving you room to settle in and enjoy the local charm. You will find options that offer a peaceful retreat, often with easy access to local attractions like Pollak Vineyards, which is about 2 miles away. Vacation rentals in Greenwood typically feature full kitchens, free parking, and high-speed internet, ensuring a convenient stay.
What are the most popular vacation rentals in Greenwood?
The most popular vacation rentals in Greenwood are houses and charming cottages. These property types are favored for their privacy, ample space, and the ability to accommodate families and groups comfortably. They offer a true home-away-from-home experience, allowing guests to enjoy the serene surroundings of Greenwood with all the conveniences of a private residence.
What amenities do vacation rentals in Greenwood usually offer?
Vacation rentals in Greenwood typically offer a range of amenities designed for a comfortable and convenient stay. You can expect full kitchens for preparing meals, free parking, and high-speed internet access. Many properties also include air conditioning, patios or yards for outdoor enjoyment, and entertainment options like TV. Some vacation rentals also provide laundry facilities, fireplaces, or even private pools, adding to the comfort of your stay.
Are there family-friendly vacation rentals in Greenwood?
Yes, most vacation rentals in Greenwood are family-friendly, with a selection of houses and cottages designed to welcome guests of all ages. These properties often come equipped with full kitchens, spacious dining areas, and microwaves, making meal preparation easy. Some family-friendly rentals also offer amenities like high chairs or outdoor play areas, providing extra convenience and fun for younger guests.
What are the best areas for group vacation rentals in Greenwood?
Greenwood offers a selection of vacation rentals suitable for groups, primarily houses that provide ample space and privacy for everyone. These properties are ideal for gatherings, featuring amenities like multiple bathrooms, large dining areas, and fully equipped kitchens for shared meals. Free parking is also commonly available, making it easy for multiple vehicles to be accommodated during your group's stay.
What are the best luxury vacation rentals in Greenwood?
Greenwood features a selection of luxury vacation rentals, predominantly houses, that offer an elevated stay experience. These upscale properties often include desirable amenities such as private pools, hot tubs, and cozy fireplaces. Guests can also enjoy spacious outdoor areas and scenic views, providing a refined and relaxing retreat in Greenwood.
Are there any budget-friendly vacation rentals in Greenwood?
Yes, Greenwood offers budget-friendly vacation rentals that provide great value for your trip, including charming cottages and houses. These properties often come with essential amenities like full kitchens, laundry facilities, and free parking, helping you save on dining out and other expenses. Choosing a vacation rental in Greenwood allows you to enjoy a comfortable stay without compromising on privacy or space.
Are there any vacation rentals in Greenwood with a hot tub?
Yes, there is a house in Greenwood that offers a hot tub, providing a relaxing amenity for your stay. This property often includes additional comforts like a fireplace, creating a cozy atmosphere for unwinding after a day of exploring the area.
Are there any short-term vacation rentals in Greenwood for a weekend getaway?
Yes, vacation rentals in Greenwood are well-suited for short-term stays and weekend getaways. You'll find houses and cottages that offer the perfect blend of privacy and comfort for a quick escape. These rentals provide a convenient base to explore local attractions, such as Pollak Vineyards, ensuring a memorable and relaxing weekend.
Are there any remote work vacation rentals in Greenwood?
Yes, Greenwood offers a vacation rental that is well-equipped for longer stays and remote work. This property provides essential amenities like fast Wi-Fi, full kitchens, and comfortable living spaces, allowing you to maintain productivity while enjoying a change of scenery. The privacy and quiet environment of a vacation rental make it an ideal choice for remote professionals.
What are the best areas for vacation rentals near Pollak Vineyards?
You'll find a selection of vacation rentals near Pollak Vineyards, primarily houses and cottages, offering convenient access to the winery. Many of these properties are within a 4-minute drive of Pollak Vineyards, with some as close as a 2-minute drive. These rentals provide a comfortable base for exploring the vineyard and the surrounding scenic area.
How much does a Greenwood vacation rental cost?
A vacation rental in Greenwood typically costs an average of $469 per night. You can find options starting from $245 per night. Prices can vary based on the size of the property, the amenities offered, and the time of year you plan to visit. For instance, February is generally the peak month for pricing, while December tends to offer the lowest rates.
How early should I book my vacation rental in Greenwood?
For a vacation rental in Greenwood, it's a good idea to book several months in advance, especially if you plan to travel during the peak season from January through March. Booking early can help you get the best selection of houses and cottages. If your travel dates are more flexible or fall within the quietest season, such as October through December, you may find more availability closer to your trip.
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.

More Vacation Ideas