Greenwood Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Greenwood vacation rentals

Luxury Apartment, Multiple Beds, Non Smoking, Garden View | Egyptian cotton sheets, premium bedding, memory foam beds

SONSAK - MONTICELLO

SONSAK - MONTICELLO
3.5 star property
Charlottesville
The price is NT$3,585
NT$4,097 total
includes taxes & fees
Jun 3 - Jun 4
SONSAK - MONTICELLO
Standard Suite, 1 Queen Bed | Private kitchen | Full-size fridge, microwave, oven, stovetop

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.2 out of 10, Wonderful, (60 reviews)
"Very good value, would definitely stay again"
United States
Frank
The price is NT$2,603
NT$2,897 total
includes taxes & fees
Jun 8 - Jun 9
Affordable Suites of America Waynesboro
Interior detail

Afton Mountain Vineyards

Afton Mountain Vineyards
2.5 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 NT$11,815
NT$13,269 total
includes taxes & fees
Jun 15 - Jun 16
Afton Mountain Vineyards
Street view

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (241 reviews)
"Stay here 2 times a year, and doesn’t disappoint."
United States
Kate
The price is NT$3,575
NT$3,979 total
includes taxes & fees
Jun 1 - Jun 2
Valley Extended Suites
Apartment, Private Bathroom (Sunflower Oasis) | 1 bedroom

Fishersville Oasis

Fishersville Oasis
2.0 star property
Fishersville
2.0 out of 10, (1 review)
The price is NT$5,175
NT$8,378 total
includes taxes & fees
Jun 1 - Jun 2
Fishersville Oasis
Ravens Roost, 3 Bedrooms, Hot Tub, Mountain View | Terrace/patio

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (17 reviews)
"Very quiet and peaceful stay. "
United States
Timika
The price is NT$4,398
NT$6,821 total
includes taxes & fees
Jun 1 - Jun 2
Love Ridge Mountain Lodging
House (3 Bedrooms) | Interior

Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is NT$7,684
NT$19,077 total
includes taxes & fees
Jun 16 - Jun 17
Modern Nellysford Getaway on 40 Private Acres!
House, Smoking | 4 bedrooms

Stoney Creek Cottage Wintergreen w EV Charger

Stoney Creek Cottage Wintergreen w EV Charger
2.0 star property
Nellysford
The price is NT$6,937
NT$15,601 total
includes taxes & fees
Jun 2 - Jun 3
Stoney Creek Cottage Wintergreen w EV Charger
Apartment, Private Bathroom (The Shenandoah Suite) | Exterior

The Shenandoah Suite

The Shenandoah Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (8 reviews)
"This was our second stay at this property (in a different apartment), and once again it did not disappoint. The space was clean, comfortable, and the kitchen was stocked with basic cooking items, though spices were minimal. The location is a big plus—easy walking distance to downtown restaurants—and we would definitely stay here again."
United States
Carrie
The price is NT$2,948
NT$5,761 total
includes taxes & fees
Jun 1 - Jun 2
The Shenandoah Suite
Apartment, Private Bathroom (North Central Loft) | Bathroom

North Central Loft

North Central Loft
2.0 star property
Staunton
10.0 out of 10, Exceptional, (5 reviews)
"Clean, comfortable, fun, well appointed and thoughtful details. A great place. "
United States
Stacey
The price is NT$6,116
NT$12,997 total
includes taxes & fees
Jun 15 - Jun 16
North Central Loft
Cabin, Private Bathroom (Blackwood Chalet) | Lounge

Blackwood Chalet

Blackwood Chalet
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (3 reviews)
"Love the area"
United States
Toni
The price is NT$6,116
NT$13,912 total
includes taxes & fees
Jun 1 - Jun 2
Blackwood Chalet
Luxury Room, Ensuite (The Storefront) | Lounge

The Storefront

The Storefront
3.5 star property
Staunton
8.8 out of 10, Excellent, (59 reviews)
"Great location, fun place to stay!"
United States
Carol
The price is NT$4,673
NT$7,115 total
includes taxes & fees
Jun 1 - Jun 2
The Storefront
Apartment, Private Bathroom (The Bohemian Suite) | Lobby

The Bohemian Suite

The Bohemian Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (6 reviews)
"It was really nice. A bit pricey. "
United States
Bonny
The price is NT$2,885
NT$5,690 total
includes taxes & fees
Jun 2 - Jun 3
The Bohemian Suite
Apartment (2 Bedrooms) | 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 NT$3,826
NT$10,652 total
includes taxes & fees
Jun 3 - Jun 4
Wintergreen Ski Resort Condo w/ Golf Access!
Apartment, Private Bathroom (The Urban Cowboy) | Exterior

The Urban Cowboy

The Urban Cowboy
2.0 star property
Staunton
8.6 out of 10, Excellent, (7 reviews)
"Great place to stay very organized and has everything you need super clean !"
United States
Philip
The price is NT$2,791
NT$5,585 total
includes taxes & fees
Jun 1 - Jun 2
The Urban Cowboy
Apartment, Private Bathroom (The Serendipity Suite) | Balcony view

The Serendipity Suite

The Serendipity Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (7 reviews)
"We loved staying at the Serendipity Suite in beautiful Staunton! It's a lovely apartment and our hosts made us feel so comfortable with all of the little thoughtful extras."
United States
Patricia
The price is NT$2,791
NT$5,585 total
includes taxes & fees
Jun 1 - Jun 2
The Serendipity Suite
Apartment, Private Bathroom (The Bons Amis Suite) | Exterior

The Bons Amis Suite

The Bons Amis Suite
2.0 star property
Staunton
9.6 out of 10, Exceptional, (4 reviews)
"We enjoyed our stay. The room is vey nice and the location is convenient to the conference center nearby."
United States
John
The price is NT$2,791
NT$5,585 total
includes taxes & fees
Jun 1 - Jun 2
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

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

10/10 Excellent
"Very clean and staff was very helpful in helping us plan restaurants and local winery!"
Shari 2-night trip
Posted less than an hour ago
Country Inn & Suites by Radisson, Charlottesville-UVA, VA

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
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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 Charlottesville Ice Park, or get out into nature at a spot like Rockfish Gap Entrance Shenandoah. In the larger area, you’ll find Pollak Vineyards and Monticello.

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.