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Greenwood Vacation Rentals

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Check prices for these dates

Tonight
Dec 20 - Dec 21
Tomorrow
Dec 21 - Dec 22
Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4

Our top choices for Greenwood vacation rentals

Studio Suite | Private kitchen | Full-size fridge, microwave, oven, stovetop
Valley Extended Suites

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (216)
"I liked the cleanliness of the suite, the fully staffed kitchen, the large bathroom, the comfortable bed, the ease and safety of the parking area."
United States
Tammy
The price is ￥17,738
￥19,742 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Valley Extended Suites
Hanging Rock Cabin, 2 Bedrooms, Jetted Tub, Mountain View | Terrace/patio
Love Ridge Mountain Lodging

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Montebello
10.0 out of 10, Exceptional, (14)
"Amazing stay I had, very peaceful and very quiet. "
United States
Abby
The price is ￥27,951
￥40,724 total
includes taxes & fees
Dec 23 - Dec 24
Love Ridge Mountain Lodging
Luxury Room, Ensuite (The Storefront) | Bar (on property)
The Storefront

The Storefront

The Storefront
3.5 star property
Staunton
8.8 out of 10, Excellent, (58)
"Great place to stay in charming Staunton!"
United States
Kate
The price is ￥23,184
￥35,302 total
includes taxes & fees
Dec 21 - Dec 22
The Storefront
Standard Suite, 1 Queen Bed | Living area | LCD TV, DVD player
Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.4 out of 10, Exceptional, (53)
"Always a pleasant stay."
United States
MARJORIE
The price is ￥13,093
￥14,572 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Affordable Suites of America Waynesboro
Terrace/patio
Affordable Suites Charlottesville

Affordable Suites Charlottesville

Affordable Suites Charlottesville
2.0 star property
Fry's Spring
8.0 out of 10, Very Good, (80)
"Simple, clean comfortable suite. Full kitchen with frig, stove and microwave. Convenient to UVA campus and football stadium. "
United States
Anonymous traveler
Affordable Suites Charlottesville
Interior detail
Afton Mountain Vineyards

Afton Mountain Vineyards

Afton Mountain Vineyards
2.5 star property
Afton
10.0 out of 10, Exceptional, (1)
"Amazing little cottage with everything you need. Loved the back porch and listening to music from the winery and enjoying the view. Good news, did not hear the music inside. "
United States
Kristin
The price is ￥48,037
￥53,944 total
includes taxes & fees
Dec 21 - Dec 22
Afton Mountain Vineyards
Apartment | 4 bedrooms
Stoney Creek Cottage Wintergreen w EV Charger

Stoney Creek Cottage Wintergreen w EV Charger

Stoney Creek Cottage Wintergreen w EV Charger
2.0 star property
Nellysford
The price is ￥54,801
￥110,501 total
includes taxes & fees
Dec 24 - Dec 25
Stoney Creek Cottage Wintergreen w EV Charger
House (3 Bedrooms) | Interior
Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is ￥52,846
￥111,900 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Modern Nellysford Getaway on 40 Private Acres!
Apartment, Private Bathroom (The Bohemian Suite) | Lobby
The Bohemian Suite

The Bohemian Suite

The Bohemian Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (6)
"It was really nice. A bit pricey. "
United States
Bonny
The price is ￥13,848
￥24,846 total
includes taxes & fees
Jan 7 - Jan 8, 2026
The Bohemian Suite
Apartment, Private Bathroom (The Serendipity Suite) | Exterior
The Serendipity Suite

The Serendipity Suite

The Serendipity Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (6)
"Cute and tidy. Easy check in and out. Easy parking and walk to dining. EV charge is for teslas, you'll need an adapter."
United States
Jennifer
The price is ￥13,848
￥24,846 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Serendipity Suite
Apartment, Private Bathroom (The Urban Cowboy) | Exterior
The Urban Cowboy

The Urban Cowboy

The Urban Cowboy
2.0 star property
Staunton
8.6 out of 10, Excellent, (7)
"The space,the location,the parking,the details! It truly felt like my apartment away from home! This place is a must stay!"
United States
Dorothy
The price is ￥13,848
￥24,846 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The Urban Cowboy
Cabin, Private Bathroom (Blackwood Chalet) | Exterior
Blackwood Chalet

Blackwood Chalet

Blackwood Chalet
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (3)
"Love the area"
United States
Toni
The price is ￥56,317
￥94,794 total
includes taxes & fees
Dec 22 - Dec 23
Blackwood Chalet
Apartment, Private Bathroom (North Central Loft) | Exterior
North Central Loft

North Central Loft

North Central Loft
2.0 star property
Staunton
10.0 out of 10, Exceptional, (3)
"Clean, comfortable, fun, well appointed and thoughtful details. A great place. "
United States
Stacey
The price is ￥28,008
￥58,599 total
includes taxes & fees
Jan 5 - Jan 6, 2026
North Central Loft
Apartment, Private Bathroom (The Shenandoah Suite) | Exterior
The Shenandoah Suite

The Shenandoah Suite

The Shenandoah Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (5)
"Well-appointed, large space conveniently located within walking distance to downtown. Comfy bed and all the expected amenities. Excellent communication. "
United States
Jani
The price is ￥13,848
￥24,846 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The Shenandoah Suite
Apartment, Private Bathroom (The Bons Amis Suite) | Lounge
The Bons Amis Suite

The Bons Amis Suite

The Bons Amis Suite
2.0 star property
Staunton
9.4 out of 10, Exceptional, (3)
"Quiet homey environment in a great location. Clean and cozy. Really appreciated the coffee and other amenities. Would definitely stay here again !"
United States
Areej
The price is ￥13,848
￥24,846 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The Bons Amis Suite
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

English Inn of Charlottesville

English Inn of Charlottesville

10/10 Excellent
"Enjoyed my stay, will definitely come back and also recommend to others!"
Hunt 2-night trip
Posted 3 days ago
English Inn of Charlottesville

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
  • Use the map to find apartments and other holiday homes in the Greenwood neighbourhood you prefer
  • 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 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.

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

Large and Luxurious Exec 5BR Chalet: This vacation home rental near Greenwood is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.