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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Greenwood holiday 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 3.344.926 ₫
3.823.224 ₫ total
includes taxes & fees
29 Apr - 30 Apr
SONSAK - MONTICELLO
Standard Suite, 1 Queen Bed | Private kitchen | Full-sized fridge, microwave, oven, stovetop

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.4 out of 10, Exceptional, (54 reviews)
"Always a pleasant stay."
United States
MARJORIE
The price is 2.185.971 ₫
2.432.986 ₫ total
includes taxes & fees
21 Apr - 22 Apr
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 10.139.745 ₫
11.386.934 ₫ total
includes taxes & fees
20 Apr - 21 Apr
Afton Mountain Vineyards
Private kitchen

Fishersville Oasis

Fishersville Oasis
2.0 star property
Fishersville
The price is 3.028.755 ₫
5.569.749 ₫ total
includes taxes & fees
28 Apr - 29 Apr
Fishersville Oasis
Street view

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (221 reviews)
"Nice place"
United States
Orhan
The price is 3.002.418 ₫
3.341.691 ₫ total
includes taxes & fees
22 Apr - 23 Apr
Valley Extended Suites
Apartment | 4 bedrooms

Stoney Creek Cottage Wintergreen w EV Charger

Stoney Creek Cottage Wintergreen w EV Charger
2.0 star property
Nellysford
The price is 5.170.307 ₫
14.002.196 ₫ total
includes taxes & fees
20 Apr - 21 Apr
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!
3.0 star property
Nellysford
The price is 6.452.565 ₫
16.020.270 ₫ total
includes taxes & fees
21 Apr - 22 Apr
Modern Nellysford Getaway on 40 Private Acres!
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, (16 reviews)
"Very quiet and peaceful stay. "
United States
Timika
The price is 3.904.881 ₫
5.965.401 ₫ total
includes taxes & fees
30 Apr - 1 May
Love Ridge Mountain Lodging
Luxury Room, Ensuite (The Storefront) | Lounge

The Storefront

The Storefront
3.5 star property
Staunton
8.8 out of 10, Excellent, (58 reviews)
"Great location, fun place to stay!"
United States
Carol
The price is 3.924.213 ₫
5.975.339 ₫ total
includes taxes & fees
17 May - 18 May
The Storefront
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 2.343.993 ₫
4.690.093 ₫ total
includes taxes & fees
27 Apr - 28 Apr
The Urban Cowboy
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 5.135.715 ₫
10.914.580 ₫ total
includes taxes & fees
19 Apr - 20 Apr
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 4.450.953 ₫
10.265.899 ₫ total
includes taxes & fees
19 Apr - 20 Apr
Blackwood Chalet
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 3.213.114 ₫
8.945.099 ₫ total
includes taxes & fees
20 Apr - 21 Apr
Wintergreen Ski Resort Condo w/ Golf Access!
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 2.343.993 ₫
4.690.093 ₫ total
includes taxes & fees
27 Apr - 28 Apr
The Serendipity Suite
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 2.343.993 ₫
4.690.093 ₫ total
includes taxes & fees
20 Apr - 21 Apr
The Bohemian 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 2.370.330 ₫
4.719.590 ₫ total
includes taxes & fees
27 Apr - 28 Apr
The Bons Amis Suite
Apartment, Private Bathroom (The Shenandoah Suite) | Exterior

The Shenandoah Suite

The Shenandoah Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (6 reviews)
"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 2.343.993 ₫
4.690.093 ₫ total
includes taxes & fees
4 May - 5 May
The Shenandoah 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

8/10 Good
"Hotel is in a great location. The rooms are fairly large and sufficiently clean. Many of the snacks for sale in the lobby were expired. "
Jamila 2-night trip
Posted 3 hours ago
Country Inn & Suites by Radisson, Charlottesville-UVA, VA

Frequently asked questions

Can I find holiday rentals in Greenwood?

Yes, there are holiday rentals close to the most popular sights in Greenwood, or you can select a more secluded option if you're looking for a relaxing stay. Greenwood is known for its wineries.

How many holiday rentals will I find in Greenwood?

With 3 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Pollak Vineyards and King Family Vineyards.

What’s a holiday rental in Greenwood like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Greenwood. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips.