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Greenwood Vacation Rentals

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Check prices for these dates

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

Our top choices for Greenwood holiday rentals

A view through a window of a lake surrounded by greenery and hills.

1. Clonmel Acres

Clonmel Acres
2.0 star property
Afton
Clonmel Acres
An outdoor seating area with a view of a vineyard.

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 RM1,576
RM1,770 total
includes taxes & fees
25 Aug - 26 Aug
Afton Mountain Vineyards

3. 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
The price is RM460
RM512 total
includes taxes & fees
25 Aug - 26 Aug
Valley Extended Suites

4. Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
Modern Nellysford Getaway on 40 Private Acres!
A spacious living room with a stone fireplace, a ceiling fan, and a large TV mounted on the wall.

5. Stoney Creek Cottage Wintergreen w EV Charger

Stoney Creek Cottage Wintergreen w EV Charger
2.0 star property
Nellysford
The price is RM676
RM1,775 total
includes taxes & fees
31 Aug - 1 Sept
Stoney Creek Cottage Wintergreen w EV Charger

6. 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 RM462
RM528 total
includes taxes & fees
25 Aug - 26 Aug
SONSAK - MONTICELLO
A two-story house with a deck, large windows, and a garage.

7. 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 RM519
RM825 total
includes taxes & fees
23 Sept - 24 Sept
Love Ridge Mountain Lodging
A wooden cabin with a sliding door, a hot tub, and string lights.

8. The Reserve at 151

The Reserve at 151
2.0 star property
Afton
10.0 out of 10, Exceptional, (1 review)
The Reserve at 151
A hotel room with a bed, a sofa, a chair, and a view of the mountains.

9. Swannanoa Guest House

Swannanoa Guest House
2.0 star property
Afton
The price is RM1,208
RM2,689 total
includes taxes & fees
22 Sept - 23 Sept
Swannanoa Guest House
A hot tub with a view of a forest and mountains through a window.

10. Fox Hill

Fox Hill
2.0 star property
Afton
The price is RM925
RM1,832 total
includes taxes & fees
3 Sept - 4 Sept
Fox Hill
A modern kitchen with white cabinets, a central island with stools, stainless steel appliances, and pendant lighting.

11. Afton Farmhouse

Afton Farmhouse
2.0 star property
Afton
The price is RM707
RM1,247 total
includes taxes & fees
7 Sept - 8 Sept
Afton Farmhouse
A residential property with a wooden deck, a small porch, and a well-lit house.

12. Kateri

Kateri
2.0 star property
Waynesboro
Kateri
A fire pit with chairs, a small house with stairs, and trees in a yard.

13. Artisan's Cottage

Artisan's Cottage
2.0 star property
Afton
The price is RM481
RM1,107 total
includes taxes & fees
25 Aug - 26 Aug
Artisan's Cottage
A kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with a kettle.

14. The Farmhouse at Wellington

The Farmhouse at Wellington
2.0 star property
Waynesboro
The Farmhouse at Wellington
A modern kitchen with a large island, dark cabinetry, and a view to the dining area.

15. Little Haven Cottage

Little Haven Cottage
2.0 star property
Afton
The price is RM683
RM1,574 total
includes taxes & fees
3 Sept - 4 Sept
Little Haven Cottage

16. The Guest Wing at Kateri

The Guest Wing at Kateri
2.0 star property
Waynesboro
The price is RM525
RM887 total
includes taxes & fees
31 Aug - 1 Sept
The Guest Wing at Kateri
A stone fire pit with a wooden bench, a white building in the background, and a grassy field with trees and mountains.

17. Afton Awaits

Afton Awaits
2.5 star property
Afton
The price is RM1,524
RM2,732 total
includes taxes & fees
22 Sept - 23 Sept
Afton Awaits
A hot tub with a wooden deck and a view of a forest.

18. Bear Tracks Cottage

Bear Tracks Cottage
2.0 star property
Nellysford
The price is RM739
RM1,646 total
includes taxes & fees
25 Aug - 26 Aug
Bear Tracks Cottage
A cabin with a porch, surrounded by trees.

19. Nelson Cozy Cabin

Nelson Cozy Cabin
2.0 star property
Nellysford
The price is RM763
RM1,651 total
includes taxes & fees
25 Aug - 26 Aug
Nelson Cozy Cabin
A wooden deck with a yellow door, a table with chairs, and a rocking chair.

20. Tucked Inn: Upper Unit

Tucked Inn: Upper Unit
2.0 star property
Nellysford
Tucked Inn: Upper Unit
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
"Me and my family love it"
Xiomara 2-night trip
Posted 15 hours ago
Holiday Inn Express & Suites Waynesboro East by IHG

Find out more about Greenwood

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

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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.

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 Charlottesville Ice Park, 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.