Holiday Homes in Greenwood

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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for Greenwood holiday homes

Property grounds

Hillside Haven: Modern Retreat, Mountain Views

Hillside Haven: Modern Retreat, Mountain Views
Faber
10.0 out of 10, Exceptional, (33 reviews)
"Fantastic property with all the amenities near UVA, and lots of wineries."
United States
roberto c.
The price is €352
includes taxes & fees
23 Feb - 24 Feb
Hillside Haven: Modern Retreat, Mountain Views
Outdoor spa tub

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, (46 reviews)
"loved the quiet location, sunny private back yard, and well-stocked kitchen"
United States
George D.
The price is €189
includes taxes & fees
9 Mar - 10 Mar
NEW! Cheerful 2 bd bungalow with hot tub. Must see!
Outdoor spa tub

Fox Hill: 151 Cottage w/Hot Tub + Mountain Views

Fox Hill: 151 Cottage w/Hot Tub + Mountain Views
Afton
10.0 out of 10, Exceptional, (14 reviews)
"This property is wonderful for a nice long weekend away in the mountains and wine country. Its proximity to many places on the Nelson 151, and the Blue Ridge Parkway is hard to beat. The hot tub is great as well."
United States
Richard S.
Fox Hill: 151 Cottage w/Hot Tub + Mountain Views
Outdoor dining

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

Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews
Nellysford
10.0 out of 10, Exceptional, (6 reviews)
"Adorable, clean and quiet stay! The place was nicer than expected. It's obvious the hosts are thoughtful of their guests - we found everything we needed and more. A short drive into Nellysford and tucked away in the trees. "
United States
Katie K.
Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews
Property grounds

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (48 reviews)
"The space was great for a getaway, highly recommended."
United States
Matt E.
The price is €101
includes taxes & fees
20 Feb - 21 Feb
The Firefly Springhouse
Interior

Charming Updated 3 Bedroom Home Near Downtown

Charming Updated 3 Bedroom Home Near Downtown
Martha Jefferson
9.8 out of 10, Exceptional, (68 reviews)
"Great location and street parking right outside the house. "
United States
sonia d.
The price is €309
includes taxes & fees
2 Mar - 3 Mar
Charming Updated 3 Bedroom Home Near Downtown
Exterior detail

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, (19 reviews)
"The perfect stay for a wedding weekend in Waynesboro. It was very warm and accommodating and I can’t say enough good things about it. Thank you for a great weekend"
United States
Michael W.
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Outdoor dining

Tucked Inn: Lower Unit - NEW Nelson Co Getaway

Tucked Inn: Lower Unit - NEW Nelson Co Getaway
Nellysford
The price is €249
includes taxes & fees
3 Mar - 4 Mar
Tucked Inn: Lower Unit - NEW Nelson Co Getaway
Terrace/patio

Farmhouse at the foot of the Blue Ridge Mountains

Farmhouse at the foot of the Blue Ridge Mountains
Waynesboro
10.0 out of 10, Exceptional, (32 reviews)
"Great stay, my dog loved running around in the fenced backyard. "
United States
Caitlin P.
Farmhouse at the foot of the Blue Ridge Mountains
Fridge, microwave, oven, stovetop

The Farmhouse at Wellington: Waynesboro, Sleeps 12

The Farmhouse at Wellington: Waynesboro, Sleeps 12
Waynesboro
10.0 out of 10, Exceptional, (6 reviews)
"The house was convenient and the downstairs was big. Kitchen was wwkl stocked. Besrooms were just what we needed."
United States
Becky R.
The price is €503
includes taxes & fees
24 Feb - 25 Feb
The Farmhouse at Wellington: Waynesboro, Sleeps 12
Smart TV, fireplace, books

Afton Farmhouse - Mountain Views off Route 151

Afton Farmhouse - Mountain Views off Route 151
Afton
9.8 out of 10, Exceptional, (26 reviews)
"We very much enjoyed our stay here. If we ever come back this will definitely be our top choice. Much older home but very well maintained."
United States
Michael S.
Afton Farmhouse - Mountain Views off Route 151
Dining

"Glass & Pine" Home close to Bold Rock & Vineyards

"Glass & Pine" Home close to Bold Rock & Vineyards
Nellysford
10.0 out of 10, Exceptional, (2 reviews)
"We only stayed one night but wished we could have stayed longer! The place was super clean and the views were beautiful once the rain finally stopped! Close to our favorite brewery and cidery. There were issues with TV reception (buffering) which may just be the area. Not much time for TV watching anyway with all the beautiful things to explore. We enjoyed our stay. "
United States
Robert H.
"Glass & Pine" Home close to Bold Rock & Vineyards
Terrace/patio

Blue's Barn: Central to Wineries & Breweries

Blue's Barn: Central to Wineries & Breweries
Nellysford
9.6 out of 10, Exceptional, (18 reviews)
"Clean, nice place"
United States
Tom
Blue's Barn: Central to Wineries & Breweries
Smart TV, stereo

Rugby Road Residential -RRR- near UVa and downtown

Rugby Road Residential -RRR- near UVa and downtown
Barracks Rugby
10.0 out of 10, Exceptional, (44 reviews)
"Great place to stay and well organized !"
United States
Joseph F.
Rugby Road Residential -RRR- near UVa and downtown
Dining

Secluded cabin on a horse farm, bordered by the North River

Secluded cabin on a horse farm, bordered by the North River
GROTTOES
10.0 out of 10, Exceptional, (72 reviews)
"Great location. Beutiful farm and very well kept animals. Would stay there again. "
United States
Jody M.
The price is €251
includes taxes & fees
20 Feb - 21 Feb
Secluded cabin on a horse farm, bordered by the North River
Smart TV, books, stereo

Honey House—beautiful modern loft near with UVA, Monticello and downtown

Honey House—beautiful modern loft near with UVA, Monticello and downtown
Charlottesville
10.0 out of 10, Exceptional, (52 reviews)
"Great location and comfortable accommodations. Can’t wait to return! "
United States
Karen W.
Honey House—beautiful modern loft near with UVA, Monticello and downtown
Fridge, microwave, oven, stovetop

The Bungalow at Afton Mountain Retreat

The Bungalow at Afton Mountain Retreat
Afton
10.0 out of 10, Exceptional, (24 reviews)
"Beautiful property! Well stocked, comfortable home close to wineries. Perfect for our group!"
United States
Eileen M.
The Bungalow at Afton Mountain Retreat
Dining

The Hawksbill Haus (w/ hot tub)

The Hawksbill Haus (w/ hot tub)
Waynesboro
9.6 out of 10, Exceptional, (10 reviews)
"Home was as described. Location was close enough to stores and attractions. Hot tub was nice."
United States
Catherine D.
The Hawksbill Haus (w/ hot tub)
2 bedrooms, free WiFi, bed sheets

Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!

Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!
Belmont
9.8 out of 10, Exceptional, (57 reviews)
"My family (4 adults) had a great time in Belmont. The location was perfect for a walk to "The Mall" and a short drive to campus for a game. The hosts were quick to respond and flexible with checking in. We would definitely stay here again."
United States
Kim E.
Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!
Fridge, microwave, oven, stovetop

Beautiful New Townhome with Mountain Views. Close to downtown!

Beautiful New Townhome with Mountain Views. Close to downtown!
Charlottesville
8.8 out of 10, Excellent, (16 reviews)
"Beautiful home in a great location."
United States
Laurene T.
The price is €444
includes taxes & fees
23 Feb - 24 Feb
Beautiful New Townhome with Mountain Views. Close to downtown!
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
"Room was spotless and staff served well. Very nice and courteous."
Juanita 1-night trip
Posted 1 day ago
Country Inn & Suites by Radisson, Charlottesville-UVA, VA

Find out more about Greenwood

Greenwood Holiday Homes information

Number of reviews
581
Accommodation
528 Holiday Homes
Lowest Price
€101
Highest Price
€503