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Greenwood Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Greenwood vacation rentals

An outdoor patio with stone flooring, string lights, and various plants.

1. Guesthouse

Guesthouse
Crozet
10.0 out of 10, Exceptional, (85 reviews)
"The property was as described ..cute.. clean.. and perfect for our overnight stay."
United States
Shelly B.
$164 nightly
The price is $187
Aug 30 - Aug 31
Total with taxes and fees
Guesthouse
A log cabin with a red door, a welcome sign, and a window with a hanging flower arrangement.

2. Willow Haven: Cozy cabin in delightful Afton

Willow Haven: Cozy cabin in delightful Afton
Afton
9.8 out of 10, Exceptional, (37 reviews)
"Communication with the host was great. It was in a beautiful private setting that was the perfect location for us, halfway home from the beach. We loved the screened in porch, very relaxing!"
United States
Sue
$227 nightly
The price is $255
Aug 30 - Aug 31
Total with taxes and fees
Willow Haven: Cozy cabin in delightful Afton
A neatly arranged bedroom with a bed, two bedside tables, a bench, and a framed floral artwork on the wall.

3. Shenandoah Valley Atelier: NEW Waynesboro Loft

Shenandoah Valley Atelier: NEW Waynesboro Loft
Waynesboro
10.0 out of 10, Exceptional, (15 reviews)
"Great place and very close to great places to eat."
United States
Kathryn H.
$229 nightly
The price is $255
Aug 30 - Aug 31
Total with taxes and fees
Shenandoah Valley Atelier: NEW Waynesboro Loft
A building facade with a blue door labeled "Stay in Crozet" and a sign above indicating overnight lodging.

4. Stay in Crozet Train Suite in Downtown Crozet

Stay in Crozet Train Suite in Downtown Crozet
Crozet
10.0 out of 10, Exceptional, (72 reviews)
"The apartment was beautifully decorated and immaculately clean. It was close to everything we intended to get to and we appreciated how easy it was to check in and check out. It was so comfortable and homey. "
United States
Natalie
$229 nightly
The price is $247
Aug 31 - Sep 1
Total with taxes and fees
Stay in Crozet Train Suite in Downtown Crozet
A wooden deck with a table and chairs, surrounded by lush greenery.

5. Wandering Bear’s Den Private Studio Near Crozet and Charlottesville

Wandering Bear’s Den Private Studio Near Crozet and Charlottesville
Charlottesville
10.0 out of 10, Exceptional, (63 reviews)
"Great setting and very clean and comfortable."
United States
Jeanie F.
$145 nightly
The price is $166
Aug 31 - Sep 1
Total with taxes and fees
Wandering Bear’s Den Private Studio Near Crozet and Charlottesville
A covered patio with a round table and chairs, a sofa, and a view of a grassy yard through large windows.

6. Rosé All Day: Wine Country Getaway! Walk to Dining

Rosé All Day: Wine Country Getaway! Walk to Dining
Crozet
9.8 out of 10, Exceptional, (32 reviews)
"It was an excellent place to stay while in Crozet. Roomy and nice house."
United States
Carolyn R.
$294 nightly
The price is $336
Aug 31 - Sep 1
Total with taxes and fees
Rosé All Day: Wine Country Getaway! Walk to Dining

7. Rockwell Ridge | Chestnut Suite with Lux Bathroom

Rockwell Ridge | Chestnut Suite with Lux Bathroom
Afton
$184 nightly
The price is $200
Sep 1 - Sep 2
Total with taxes and fees
Rockwell Ridge | Chestnut Suite with Lux Bathroom
A building facade with a blue door labeled "Stay in Crozet" and a sign above indicating overnight lodging.

8. Stay in Crozet Mountain Suite in Downtown Crozet

Stay in Crozet Mountain Suite in Downtown Crozet
Crozet
10.0 out of 10, Exceptional, (124 reviews)
"We enjoyed our stay and our host Amy was very accommodating and easy to reach."
United States
Lynn K.
$229 nightly
The price is $247
Aug 30 - Aug 31
Total with taxes and fees
Stay in Crozet Mountain Suite in Downtown Crozet

9. Rockwell Ridge | Private Retreat w/ Mountain Views

Rockwell Ridge | Private Retreat w/ Mountain Views
Afton
$727 nightly
The price is $782
Sep 15 - Sep 16
Total with taxes and fees
Rockwell Ridge | Private Retreat w/ Mountain Views
A modern kitchen with blue cabinets, a stainless steel refrigerator, and a wooden barn door.

10. The Barn at Haden near Wineries and C'ville

The Barn at Haden near Wineries and C'ville
Crozet
10.0 out of 10, Exceptional, (130 reviews)
"Location is amazing and the place is so cute! Would definitely stay again! "
United States
Crystal L.
$263 nightly
The price is $291
Sep 7 - Sep 8
Total with taxes and fees
The Barn at Haden near Wineries and C'ville

11. Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (253 reviews)
"Stay here 2 times a year, and doesn’t disappoint."
United States
Kate
$114 nightly
The price is $127
Aug 30 - Aug 31
Total with taxes and fees
Valley Extended Suites
A rustic wooden cabin with a porch, surrounded by dense foliage and a stone pathway.

12. Unique Cypress cottage, close to Charlottesville with mountain views.

Unique Cypress cottage, close to Charlottesville with mountain views.
Charlottesville
10.0 out of 10, Exceptional, (64 reviews)
"Great stay, very friendly, responsive owners."
United States
David F.
$256 nightly
The price is $293
Aug 30 - Aug 31
Total with taxes and fees
Unique Cypress cottage, close to Charlottesville with mountain views.
A hot tub with a control panel, surrounded by a backyard with trees and a house in the background.

13. NEW! Cheerful 2 bd bungalow with hot tub. Must see!

NEW! Cheerful 2 bd bungalow with hot tub. Must see!
Waynesboro
9.8 out of 10, Exceptional, (59 reviews)
"Place was exactly as described. We were only passing through for one night but was exactly what we needed. Fenced in backyard for the dog with lots of space."
United States
Brian T.
$185 nightly
The price is $206
Aug 31 - Sep 1
Total with taxes and fees
NEW! Cheerful 2 bd bungalow with hot tub. Must see!
A house with a white exterior, a window with a hanging plant, and a garden with hydrangea flowers.

14. The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Waynesboro
10.0 out of 10, Exceptional, (23 reviews)
"Owner was communicative. Lots of space. Decor was unique."
United States
Clement
$170 nightly
The price is $189
Sep 8 - Sep 9
Total with taxes and fees
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
A restaurant interior with a wooden floor, a bar area, and a seating section with a large mirror and a brown leather chair.

15. High Street | Walk to Everything Crozet | Pet-Friendly

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (113 reviews)
"This cute home was perfect for our stay in Crozet! It was close to lovely coffee shops. The home was very clean and communication with the host was fantastic! We would stay here again if in the area."
United States
Jody L.
$315 nightly
The price is $339
Aug 30 - Aug 31
Total with taxes and fees
High Street | Walk to Everything Crozet | Pet-Friendly
A rustic wooden building with a steeply pitched roof, a central entrance with a door, and a small window above the door.

16. Ivy Rose Cottage nestled b/t Cville & Vineyards

Ivy Rose Cottage nestled b/t Cville & Vineyards
Charlottesville
10.0 out of 10, Exceptional, (92 reviews)
"Place was perfect! Was a just right distance from the bustle of Charlottesville!"
United States
Bobby T.
$295 nightly
The price is $337
Aug 30 - Aug 31
Total with taxes and fees
Ivy Rose Cottage nestled b/t Cville & Vineyards
A rustic wooden cabin with a sign reading "Rusty's Retreat." It features large windows, a door, and is surrounded by a garden with plants and a large tree.

17. Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
Afton
9.6 out of 10, Exceptional, (18 reviews)
"Beautiful little spot. We will definitely be back."
United States
Caitlin S.
$153 nightly
The price is $169
Sep 7 - Sep 8
Total with taxes and fees
Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
A modern living room with a large mirror, a coffee table, and a seating area with sofas.

18. The Branch at Afton Mountain Retreat

The Branch at Afton Mountain Retreat
Afton
10.0 out of 10, Exceptional, (38 reviews)
"Very comfortable stay with friends for a wedding at Veritas Winery. Close to winery and other attractions. Would definitely book this location again."
United States
Mark U.
$412 nightly
The price is $444
Aug 30 - Aug 31
Total with taxes and fees
The Branch at Afton Mountain Retreat
A living room with a fireplace, a sofa with cushions, a coffee table, and a TV mounted above the fireplace.

19. Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
9.8 out of 10, Exceptional, (59 reviews)
"Nice resort"
United States
Diana J.
$166 nightly
The price is $187
Aug 31 - Sep 1
Total with taxes and fees
Where the Trail Ends
A compact kitchen with white cabinetry, a blue door, and a white refrigerator.

20. Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy

Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Ivy
10.0 out of 10, Exceptional, (53 reviews)
"House was quiet and peaceful. We enjoyed our stay. "
United States
Chris R.
$165 nightly
The price is $188
Sep 1 - Sep 2
Total with taxes and fees
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Greenwood Hotel Reviews

Holiday Inn Express & Suites Waynesboro East by IHG

Holiday Inn Express & Suites Waynesboro East by IHG

10/10 Excellent
"Upon arrival, we were greeted at the front desk with a smile. In fact, every employee we encountered went above and beyond expectations. Rooms were clean and comfortable. Definitely staying here again on our next trip to the Waynesboro area!"
Carrie 2-night trip
Posted 2 hours ago
Holiday Inn Express & Suites Waynesboro East by IHG

Find out more about Greenwood

Everything you need to know about Greenwood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Greenwood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greenwood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Greenwood vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greenwood. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Greenwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $127 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Greenwood rentals

At Expedia, we put the best Greenwood vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Greenwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greenwood vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greenwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Greenwood?

Yes, there are vacation rentals close to top sights in Greenwood, or you can select a more remote option if you're looking for a relaxing stay. Greenwood is known for its wineries.

What are some of the best vacation rentals that Greenwood has to offer?

RiverFront Country Home with Blue Mountain Views: This vacation home rental near Greenwood is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Greenwood?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Greenwood stay.

What’s there to see and do in Greenwood?

Explore the area and family-friendly sights such as Virginia Discovery Museum, or get out into nature at a spot like Rockfish Gap Entrance Shenandoah. In the larger area, you’ll find Pollak Vineyards and King Family Vineyards.

What’s a vacation rental in Greenwood like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Greenwood. Vacation rentals offer extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for family trips or small group gatherings.