Photo by Karyn Leary

Greenwood holiday homes

We found 214 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Scroll through and select from holiday rentals in Greenwood to find one that's perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the amenities that you need and want, which might include parking and a fireplace. No matter what you're looking for, you're sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Book a holiday 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 trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Greenwood

Are you looking for attractions to see in the area? Venture out of your cosy holiday rental and check out everything that Greenwood has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • King Family Vineyards (2.4 mi / 3.8 km)
  • Veritas Vineyard and Winery (4.7 mi / 7.5 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)
  • Blenheim Vineyards (17 mi / 27.4 km)

Exploring the natural landscape of Greenwood

Whether you're looking for adventure or just want to appreciate the scenery, Greenwood is a great place to get out in nature. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Shenandoah National Park (17.2 mi / 27.6 km)
  • Rockfish Gap Entrance Shenandoah (4.8 mi / 7.7 km)
  • Blue Ridge Parkway North Entrance (5 mi / 8 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 centre. If you can't find a flight that's convenient for your trip, you could also fly into Charlottesville, VA (CHO-Charlottesville-Albemarle), which is 18.7 mi (30.1 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Greenwood?

Based on our research, houses are the most popular holiday home type in Greenwood. But as you'd expect, everyone's idea of an epic stay isn't the same. Bookabach has holiday homes of all sizes, shapes and budgets, so you're sure to discover your ideal fit.

How much does it cost to rent a holiday home in Greenwood?

Several things can influence how much you pay for a holiday home in Greenwood, including the length of stay, type of property and season. Still, all of our holiday homes have one thing in common — incredible value. Simply enter your travel dates to find your dream escape.

How much does it cost to rent a beach house in Greenwood?

Prices for beach houses in Greenwood vary depending on the size and type of the property and when you plan to travel. Simply enter your dates of travel into Bookabach and the number of guests to view your holiday home options and prices. From there you can use our filters to narrow your search results by ratings, amenities, nearby activities and more.

Are there pet-friendly holiday homes in Greenwood?

Pack a tug toy and treats for your canine companion because Greenwood has four properties that throw open their doors to pets. Let your furriest pal join in on the family trip at one of our pet-friendly holiday homes on Bookabach. Simply enter your destination and travel dates, then check our "Pets allowed" filter box.

What are popular home amenities in Greenwood?

A chef, a barbecue grill and a sauna head the list of most popular home amenities in Greenwood. Whether you're taking a trip by yourself, with your spouse or a bunch of friends, Bookabach can help you find a holiday home that matches your style with all the conveniences you're looking for.

Are there large group holiday homes in Greenwood?

Yes, you can choose one of three holiday homes in Greenwood that can accommodate a group of five or more guests. From family trips to events like a friend's birthday, these stays have ample room to chill out with the people that matter the most.

Are there holiday homes in Greenwood that welcome kids?

Greenwood has four family-friendly holiday homes. And finding a stay that welcomes little ones is easy with Bookabach's "Properties good for families" filter. As well as having the entire place to yourselves, you'll have access to perks and conveniences like multiple bedrooms, full kitchens and private pools.

What are the top attractions for families in Greenwood?

Keep your kids busy at these top family-friendly attractions in Greenwood:

  • Waynesboro Heritage Museum
  • Zeus Digital Theatre
  • Shenandoah Valley Art Centre

How can I find holiday homes with air conditioning in Greenwood?

Greenwood has four holiday homes where you'll be able to kick back in air-conditioned comfort. To locate a property on Bookabach offering this amenity, enter your dates of travel and use the filters to select the "air conditioning" box.

How old do you have to be to rent a holiday home in Greenwood?

The minimum age requirements can differ between properties on Bookabach, so be sure to look at the rules of the holiday home in Greenwood you're interested in. But normally, it's 16, 18 or 21.

How long can I rent a holiday home in Greenwood for?

The length of time you can rent a holiday home in Greenwood is down to the property. Just enter your selected dates to see a list of options offering extended stays. With plenty of features such as kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to discover the perfect place to call your home away from home in Greenwood.

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