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Greenwood Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Greenwood holiday rentals

Exterior

1. Art & Soul

Art & Soul
2.0 star property
Nellysford
The price is HK$5,493
HK$6,169 total
includes taxes & fees
17 Aug - 18 Aug
Art & Soul
Interior detail

2. Afton Mountain Vineyards

Afton Mountain Vineyards
3.0 star property
Afton
7.4 out of 10, Good, (3 reviews)
"Cozy and comfortable with pond and mountain views. Wine tasting on site and easy access to Wintergreen. We loved our stay and will be back again!"
United States
Jennifer
The price is HK$3,062
HK$3,438 total
includes taxes & fees
17 Aug - 18 Aug
Afton Mountain Vineyards
Street view

3. Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (252 reviews)
"Stay here 2 times a year, and doesn’t disappoint."
United States
Kate
The price is HK$895
HK$996 total
includes taxes & fees
17 Aug - 18 Aug
Valley Extended Suites
Egyptian cotton sheets, premium bedding, memory-foam beds

4. SONSAK - MONTICELLO

SONSAK - MONTICELLO
3.5 star property
Charlottesville
10.0 out of 10, Exceptional, (3 reviews)
"Our stay was perfect. Hotels.com really messed up the booking and I almost didn’t have a place to stay. The host at this property held the room for me and we handled everything directly. He was great, the room was spectacular!"
United States
Crystal
The price is HK$897
HK$1,025 total
includes taxes & fees
17 Aug - 18 Aug
SONSAK - MONTICELLO
Interior

5. Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is HK$2,142
HK$5,101 total
includes taxes & fees
17 Aug - 18 Aug
Modern Nellysford Getaway on 40 Private Acres!
Terrace/patio

6. Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (22 reviews)
"Very quiet and peaceful stay. "
United States
Timika
The price is HK$1,008
HK$1,603 total
includes taxes & fees
14 Sept - 15 Sept
Love Ridge Mountain Lodging
4 bedrooms

7. Stoney Creek Cottage Wintergreen w EV Charger

Stoney Creek Cottage Wintergreen w EV Charger
2.0 star property
Nellysford
The price is HK$1,352
HK$3,494 total
includes taxes & fees
1 Sept - 2 Sept
Stoney Creek Cottage Wintergreen w EV Charger
Exterior

8. On Mountain Time

On Mountain Time
2.5 star property
Roseland
The price is HK$2,346
HK$5,499 total
includes taxes & fees
17 Aug - 18 Aug
On Mountain Time
Exterior

9. The Reserve at 151

The Reserve at 151
2.0 star property
Afton
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,797
HK$4,662 total
includes taxes & fees
17 Aug - 18 Aug
The Reserve at 151
1 bedroom

10. Swannanoa Guest House

Swannanoa Guest House
2.0 star property
Afton
The price is HK$2,346
HK$5,224 total
includes taxes & fees
24 Aug - 25 Aug
Swannanoa Guest House
Interior

11. Afton Farmhouse

Afton Farmhouse
2.0 star property
Afton
The price is HK$1,373
HK$2,423 total
includes taxes & fees
17 Aug - 18 Aug
Afton Farmhouse
Interior

12. The Wayne Shire

The Wayne Shire
2.0 star property
Waynesboro
The Wayne Shire
Outdoor spa tub

13. Fox Hill

Fox Hill
2.0 star property
Afton
The price is HK$1,797
HK$3,560 total
includes taxes & fees
24 Aug - 25 Aug
Fox Hill
Interior

14. The Farmhouse at Wellington

The Farmhouse at Wellington
2.0 star property
Waynesboro
The price is HK$1,773
HK$4,376 total
includes taxes & fees
18 Aug - 19 Aug
The Farmhouse at Wellington
Shared kitchen

15. Little Haven Cottage

Little Haven Cottage
2.0 star property
Afton
The price is HK$1,326
HK$3,059 total
includes taxes & fees
19 Aug - 20 Aug
Little Haven Cottage
Exterior

16. Artisan's Cottage

Artisan's Cottage
2.0 star property
Afton
The price is HK$934
HK$2,150 total
includes taxes & fees
31 Aug - 1 Sept
Artisan's Cottage
Terrace/patio

17. Tucked Inn: Upper Unit

Tucked Inn: Upper Unit
2.0 star property
Nellysford
The price is HK$824
HK$2,247 total
includes taxes & fees
17 Aug - 18 Aug
Tucked Inn: Upper Unit
View from property

18. Afton Awaits

Afton Awaits
2.5 star property
Afton
The price is HK$1,928
HK$4,148 total
includes taxes & fees
26 Aug - 27 Aug
Afton Awaits
Exterior

19. Tucked Inn: Lower Unit

Tucked Inn: Lower Unit
2.0 star property
Nellysford
The price is HK$785
HK$2,203 total
includes taxes & fees
17 Aug - 18 Aug
Tucked Inn: Lower Unit
Shared kitchen

20. Afton Clubhouse

Afton Clubhouse
2.0 star property
Afton
The price is HK$2,268
HK$4,309 total
includes taxes & fees
17 Aug - 18 Aug
Afton Clubhouse
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

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

10/10 Excellent
"Great location!"
Sabrina 6-night trip
Posted 6 hours ago
Country Inn & Suites by Radisson, Charlottesville-UVA, VA

Find out more about Greenwood

Search for holiday rentals in Greenwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Greenwood using one of the methods below:

  • View our selection of featured holiday rentals in Greenwood
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  • Enter your travel dates to view the best deals on holiday rentals in Greenwood while they last

Look no further and take a look at our great range of rental properties in Greenwood!

Frequently asked questions

Can I find holiday rentals in Greenwood?

Yes, there are holiday rentals close to the most popular sights in Greenwood, or you can select a more secluded option if you're looking for a relaxing stay. Greenwood is known for its wineries.

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

RiverFront Country Home with Blue Mountain Views: This holiday home rental outside of Greenwood is located on a river, and has a patio, a garden and a BBQ 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 that you can cook with friends or family.

How many holiday rentals will I find in Greenwood?

With 3 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Pollak Vineyards and King Family Vineyards.

What’s a holiday rental in Greenwood like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Greenwood. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips.