Photo by Karyn Leary

Greenwood holiday homes

We found 284 holiday rentals — enter your dates for availability
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.

Holiday rentals with weekly discounts – Greenwood

Showing deals for:1 Jan - 8 Jan

Hot tub with a view of the mountains, pool, stars!
Kitchen showing dishwasher, sink area, and refrigerator, range & table
Front hall looking toward the front entry door
Pool & House at night
Exceptional
(7 reviews)

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

Crozet

8% off
NZ$10,738
for 7 nights, 1 home
NZ$1,534 per night
includes taxes & fees
Heated Pool, Hot Tub, panoramic mountain views, near Vineyards + UVA
Interior
Private kitchen
Exterior
Private kitchen
Exceptional
(62 reviews)

Rockfish Farmhouse - Home In the heart of The Rockfish Valley

Afton

8% off
NZ$4,546
for 7 nights, 1 home
NZ$649 per night
includes taxes & fees
Rockfish Farmhouse - Home In the heart of The Rockfish Valley
Room
Great mountain views, with relaxing pond.
Private kitchen
Living area
Exceptional
(67 reviews)

Suite in Shenandoah Valley

Waynesboro

6% off
NZ$2,318
for 7 nights, 1 home
NZ$331 per night
includes taxes & fees
Suite in Shenandoah Valley
Dual sinks, quiet appliances, quartz counters, convection range, laundry closet.
Interior
Steps from the parking area to the front lawn
A view of the North and rear from Stagecoach Road - pre-2022 metal roof
Exceptional
(166 reviews)

Afton Station Cottage -Beautifully Renovated Blue Ridge Scenic Historic Setting

Afton

8% off
NZ$3,780
for 7 nights, 1 home
NZ$540 per night
includes taxes & fees
Afton Station Cottage -Beautifully Renovated Blue Ridge Scenic Historic Setting
Living area
Afton Cabin Firepit
Afton Cabin Front
Living area
Exceptional
(28 reviews)

Afton Escape! NEW Arcade, Wineries, Breweries

Afton

7% off
NZ$9,205
for 7 nights, 1 apartment
NZ$1,315 per night
includes taxes & fees
Afton Escape! NEW Arcade, Wineries, Breweries
Private kitchen
Outdoor dining
Exterior
Dining
Exceptional
(8 reviews)

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

Afton

8% off
NZ$4,308
for 7 nights, 1 cottage
NZ$615 per night
includes taxes & fees
Perfect getaway at foothills of the Blue Ridge Mountains, with gorgeous views!
Living area
Dining
Room
Private kitchen
Wonderful
(12 reviews)

The Hawksbill Haus (w/ hot tub)

Waynesboro

8% off
NZ$3,436
for 7 nights, 1 home
NZ$491 per night
includes taxes & fees
The Hawksbill Haus (w/ hot tub)
kitchen bar between kitchen and dining room
Lots of natural light in this super cute kitchen with new granite countertops.
living room
Interior
Exceptional
(53 reviews)

Coin Cottage farmhouse on 151 Trail in Nelson County

Afton

8% off
NZ$4,484
for 7 nights, 1 home
NZ$641 per night
includes taxes & fees
Coin Cottage farmhouse on 151 Trail in Nelson County
4 person table with lots of natural light
Exterior
Room
Dining
Exceptional
(26 reviews)

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

Faber

16% off
NZ$10,581
for 7 nights, 1 home
NZ$1,512 per night
includes taxes & fees
Oasis on 151 • Hot Tub • Pool Table • Huge Home
Room
Exterior
Private kitchen
Dining
Exceptional
(10 reviews)

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

Waynesboro

16% off
NZ$2,064
for 7 nights, 1 home
NZ$295 per night
includes taxes & fees
Cute Place 2yrs old near 2 Ski resorts, Many Wineries/Breweries, BR Parkway, .

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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)
  • 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 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:

  • 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 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 best area to stay in Greenwood when booking a holiday rental?
When considering a holiday rental in Greenwood, Virginia, the area surrounding the scenic countryside is particularly appealing. This charming region is known for its tranquil atmosphere and beautiful landscapes, making it an ideal retreat for those looking to escape the hustle and bustle of city life.In Greenwood, you'll find a range of properties that cater to various preferences, from quaint cottages to spacious homes, ensuring there's something for everyone. The neighbourhood is also conveniently located near some delightful attractions. For instance, you can explore the stunning views at the nearby Monticello, the historic home of Thomas Jefferson, which offers guided tours and beautiful gardens to wander through. Additionally, the picturesque vineyards in the surrounding area provide an excellent opportunity for wine tasting and a relaxing day out.
What is the most popular type of holiday rental accomodation in Greenwood?
In Greenwood, cottages and holiday houses are the most popular types of holiday rental accommodations, with several options available throughout the area. These rentals typically feature comfortable living spaces, fully equipped kitchens, and outdoor areas that allow guests to enjoy the surrounding natural beauty. Many of these properties are set in tranquil locations, making them ideal for families or groups seeking a peaceful retreat.
Are there any family house rentals in Greenwood?
In Greenwood, Virginia, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The area offers a mix of charming homes that often feature spacious living areas, fully equipped kitchens for family meals, and outdoor spaces where kids can enjoy some fresh air.Visitors can explore nearby attractions like the picturesque Blue Ridge Mountains, superb for hiking and outdoor activities, as well as local wineries that provide a lovely way for adults to relax while the kids play.
Are there any remote work holiday rentals in Greenwood?
In Greenwood, Virginia, there are several remote work holiday rentals available, making it an appealing choice for those looking to combine work and leisure. Many of these properties offer essential amenities for remote work, such as free Wi-Fi, dedicated workspaces with desks, and printers, ensuring that guests can stay productive while enjoying the serene surroundings.The area is characterised by its beautiful countryside and proximity to local attractions like the scenic Blue Ridge Parkway and nearby wineries, providing excellent opportunities for relaxation after a workday. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Greenwood?
In Greenwood, popular holiday rentals typically feature a range of amenities that enhance the comfort of guests. Most properties include a well-equipped kitchen, allowing travellers to prepare their own meals, as well as a coffee and tea maker for a convenient caffeine fix. Many rentals also provide a deck or patio, superb for enjoying the peaceful surroundings and fresh air. A desk is often available, making it suitable for those who may need to work during their stay. Onsite parking is another common amenity, ensuring guests have easy access to their vehicles.
What are the top attractions in Greenwood?
In Greenwood, Virginia, visitors can enjoy a mix of natural beauty and local charm. The area is surrounded by picturesque landscapes, making it a great spot for outdoor activities such as hiking and birdwatching, particularly in the nearby Blue Ridge Mountains. The Appalachian Trail is accessible from various points close to Greenwood, offering stunning views and a chance to connect with nature.The local wineries, such as those along the Monticello Wine Trail, attract wine enthusiasts and provide tasting experiences amidst beautiful vineyard settings. Additionally, the nearby town of Charlottesville, just a short drive away, is home to historical attractions like Thomas Jefferson's Monticello and the vibrant Downtown Mall, which features a variety of shops, restaurants, and cultural events.For those interested in history, the surrounding areas hold a wealth of Civil War sites and heritage trails.
Are all fees included in the Greenwood holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Greenwood holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Greenwood 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 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.
Are there any discounts for Greenwood holiday homes?
You can find great discounts on holiday homes in Greenwood on Bookabach, 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.
Can I change or cancel my Greenwood holiday home booking on Bookabach?
To find Greenwood holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Greenwood?
A long-stay holiday home in Greenwood 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach'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 favourites, and build the perfect itinerary together.
How early should I book a Greenwood holiday home?
Book your Greenwood holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Greenwood?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Greenwood to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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