Greenwood Holiday Homes from £89: Search Holiday Homes in Greenwood

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Our top choices for Greenwood holiday homes

A room with a brown leather sofa, a wooden bench, and a window with curtains.

1. Rockwell Ridge | Inn with Afton Mountain Views

Afton

includes taxes & fees

3 Nov - 4 Nov

A house with a white exterior, a window with a hanging plant, and a garden with hydrangea flowers.

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

Waynesboro

Elisa G.

includes taxes & fees

21 Oct - 22 Oct

A bedroom with a large bed, a bedside table with a lamp, a wooden ceiling, and a view of a dining area with a table and chairs.

3. Rockwell Ridge | Chestnut Suite with Lux Bathroom

Afton

"This property was spotlessly clean, carefully and well furnished, with clear instructions about everything. The location was peaceful and quiet, and we were treated to seeing a doe and young fawn not long after arriving. With no traffic or other noise, we had a restful stay.The host's communications were welcoming and comprehensive.While off the main roads, it is still convenient to attractions and amenities in Waynesboro. This is a perfect place to unwind; with several more rooms on the...

Peter & Stephanie R.

includes taxes & fees

16 Nov - 17 Nov

A hot tub with a control panel, surrounded by a backyard with trees and a house in the background.

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

Waynesboro

Kathleen

includes taxes & fees

26 Oct - 27 Oct

A small, dark blue building with a wooden door and windows, a sign above the door, and a small porch area.

5. Rockwell Ridge | Dogwood Suite with Clawfoot Tub

Afton

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with white cabinets, a central island with stools, stainless steel appliances, and pendant lighting.

6. Afton Farmhouse

Afton

includes taxes & fees

21 Oct - 22 Oct

7. Charming Vacation Rental in a Barn on a Horse Farm near Afton Mountain in Virginia

Afton

Shannon P.

includes taxes & fees

26 Oct - 27 Oct

A modern kitchen with a large window, stainless steel appliances, and wooden cabinetry.

8. Rockwell Ridge | Private Retreat w/ Mountain Views

Afton

includes taxes & fees

1 Nov - 2 Nov

A cozy living room with wooden paneling, a fireplace, a grey sofa, and a round coffee table.

9. Afton Farmhouse - Mountain Views off Route 151

Afton

Traci S.

includes taxes & fees

18 Nov - 19 Nov

A dining area with a wooden table and chairs, a blackboard with coffee-related drawings, and a coffee machine.

10. The Hawksbill Haus (w/ hot tub)

Waynesboro

Rose P.

includes taxes & fees

9 Nov - 10 Nov

A stone staircase leading to a wooden house with a door and a poster on the wall.

11. The Firefly Springhouse

Staunton

David H

includes taxes & fees

21 Oct - 22 Oct

A modern kitchen with green cabinets, stainless steel appliances, and a dining area with a blue wall and a poster.

12. Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews

Nellysford

Katie K.

A spacious kitchen with a large island, dark cabinetry, and a stone pendant light.

13. Mountain Mama- Amazing Views! + Hot Tub!

Afton

Maura F.

A spacious kitchen with a central island, a dining area with a table and chairs, and a black leather sofa.

14. Blue Ridge Beau, Lost In The View

Afton

Michael V.

includes taxes & fees

18 Nov - 19 Nov

A lush garden with a variety of plants and trees, a well-maintained lawn, and a distant mountain range under a partly cloudy sky.

15. Amazing Mountain Views, Hot Tub and Close to Wineries and Breweries

Afton

Catherine S.

includes taxes & fees

3 Nov - 4 Nov

A wooden cabin with a stone exterior, a balcony with wooden railings, and outdoor seating with Adirondack chairs.

16. Tucked Inn: Lower Unit

Nellysford

includes taxes & fees

15 Nov - 16 Nov

A circular stone fire pit with two Adirondack chairs around it, set on a gravel surface.

17. Peaceful Retreat w/ Hot Tub, Fire Pit, Mountain Views

Afton

Amber

includes taxes & fees

9 Nov - 10 Nov

18. Cozy Ground Floor Suite in a Beautiful Farmhouse for a Unique Getaway in Afton, Virginia

Afton

"Quiet, Peaceful, absolutely beautiful setting. We stayed in Earth room. If you can envision days gone by where a family lived in one room and stories were told by the fire- this is a modern day version. We loved that all of us were together versus siloed in separate rooms. We also thoroughly enjoyed the gardens and trails around the property. There are many places to sit and connect with nature. "

Jessica P.

includes taxes & fees

25 Oct - 26 Oct