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Greenwood Vacation Rentals

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Greenwood vacation rentals

Private kitchen

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.4 out of 10, Exceptional, (63 reviews)
"Very good value, would definitely stay again"
United States
Frank
The price is P4,802
P5,345 total
includes taxes & fees
Jun 23 - Jun 24
Affordable Suites of America Waynesboro
Exterior

Bluebird Cottage

Bluebird Cottage
2.0 star property
Roseland
The price is P6,990
P16,383 total
includes taxes & fees
Jun 22 - Jun 23
Bluebird Cottage
Street view

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (245 reviews)
"Stay here 2 times a year, and doesn’t disappoint."
United States
Kate
The price is P6,929
P7,713 total
includes taxes & fees
Jun 23 - Jun 24
Valley Extended Suites
Egyptian cotton sheets, premium bedding, memory foam beds

SONSAK - MONTICELLO

SONSAK - MONTICELLO
3.5 star property
Charlottesville
10.0 out of 10, Exceptional, (1 review)
"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 P6,948
P7,941 total
includes taxes & fees
Jul 12 - Jul 13
SONSAK - MONTICELLO
4 bedrooms

Stoney Creek Cottage Wintergreen w EV Charger

Stoney Creek Cottage Wintergreen w EV Charger
2.0 star property
Nellysford
Stoney Creek Cottage Wintergreen w EV Charger
Interior

Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is P14,892
P36,974 total
includes taxes & fees
Jun 24 - Jun 25
Modern Nellysford Getaway on 40 Private Acres!
Interior detail

Afton Mountain Vineyards

Afton Mountain Vineyards
3.0 star property
Afton
10.0 out of 10, Exceptional, (2 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 P23,718
P26,635 total
includes taxes & fees
Jun 23 - Jun 24
Afton Mountain Vineyards
Terrace/patio

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (18 reviews)
"Very quiet and peaceful stay. "
United States
Timika
The price is P8,525
P13,221 total
includes taxes & fees
Jun 22 - Jun 23
Love Ridge Mountain Lodging
Lounge

Firefly on The Ridge

Firefly on The Ridge
2.0 star property
Nellysford
The price is P10,941
P20,820 total
includes taxes & fees
Jun 30 - Jul 1
Firefly on The Ridge
Front of property

Wintergreen Ski Resort Condo w/ Golf Access!

Wintergreen Ski Resort Condo w/ Golf Access!
4.0 star property
Nellysford
10.0 out of 10, Exceptional, (2 reviews)
"Really nice and convenient condo. Great amenities. Would definitely stay again."
United States
Matthew
The price is P7,416
P20,645 total
includes taxes & fees
Jun 25 - Jun 26
Wintergreen Ski Resort Condo w/ Golf Access!
Interior

Clonmel Acres

Clonmel Acres
2.0 star property
Afton
Clonmel Acres
Terrace/patio

Tucked Inn: Upper Unit

Tucked Inn: Upper Unit
2.0 star property
Nellysford
The price is P6,382
P17,407 total
includes taxes & fees
Jun 22 - Jun 23
Tucked Inn: Upper Unit
Outdoor spa tub

Fox Hill

Fox Hill
2.0 star property
Afton
The price is P13,920
P27,578 total
includes taxes & fees
Jul 21 - Jul 22
Fox Hill
Exterior

Bear Tracks Cottage

Bear Tracks Cottage
2.0 star property
Nellysford
The price is P11,124
P24,779 total
includes taxes & fees
Jun 22 - Jun 23
Bear Tracks Cottage
Exterior

Laurelwood Hollow

Laurelwood Hollow
2.0 star property
Nellysford
The price is P5,775
P15,603 total
includes taxes & fees
Jul 19 - Jul 20
Laurelwood Hollow
Exterior

The Reserve at 151

The Reserve at 151
2.0 star property
Afton
The Reserve at 151
Terrace/patio

Staunton Underground

Staunton Underground
2.0 star property
Staunton
The price is P5,410
P12,867 total
includes taxes & fees
Jun 22 - Jun 23
Staunton Underground
Exterior

Tucked Inn: Lower Unit

Tucked Inn: Lower Unit
2.0 star property
Nellysford
The price is P6,079
P17,065 total
includes taxes & fees
Jun 22 - Jun 23
Tucked Inn: Lower Unit
Exterior

Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
Mountain Mindset
1 bedroom

Panoramic Peak

Panoramic Peak
2.0 star property
Nellysford
The price is P8,449
P15,632 total
includes taxes & fees
Jun 22 - Jun 23
Panoramic Peak
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

Motel 6 Staunton, VA

Motel 6 Staunton, VA

8/10 Good
"Looks like the hotel is in the middle of a remodel, pool was closed, must be a good place for construction workers, lots of boots sitting outside of the rooms. Staff was friendly. Rooms where nothing fancy, very sparce with furniture and decor. Really had to push to get the door to close and lock to latch."
WILLIAM 1-night trip
Posted less than an hour ago
Motel 6 Staunton, VA

Find out more about Greenwood

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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 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.

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 War Fields, 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.