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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Greenwood holiday rentals

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 9.178.400 ₫
10.307.343 ₫ total
includes taxes & fees
15 Mar - 16 Mar
Afton Mountain Vineyards
Miscellaneous

Fishersville Oasis

Fishersville Oasis
2.0 star property
Fishersville
The price is 3.015.760 ₫
5.545.852 ₫ total
includes taxes & fees
15 Mar - 16 Mar
Fishersville Oasis
Street view

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (217 reviews)
"Clean room great location quiet area"
United States
Krista
The price is 2.989.536 ₫
3.327.353 ₫ total
includes taxes & fees
16 Mar - 17 Mar
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 4.266.210 ₫
12.416.858 ₫ total
includes taxes & fees
12 Mar - 13 Mar
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 6.437.865 ₫
15.983.774 ₫ total
includes taxes & fees
24 Mar - 25 Mar
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 3.257.492 ₫
5.231.603 ₫ total
includes taxes & fees
15 Mar - 16 Mar
Love Ridge Mountain Lodging
Apartment, Private Bathroom (North Central Loft) | Bathroom

North Central Loft

North Central Loft
2.0 star property
Staunton
10.0 out of 10, Exceptional, (4 reviews)
"Clean, comfortable, fun, well appointed and thoughtful details. A great place. "
United States
Stacey
The price is 5.113.680 ₫
10.867.750 ₫ total
includes taxes & fees
16 Mar - 17 Mar
North Central Loft
House | 4 bedrooms

Waynesboro Home Near Wintergreen Charlottesville

Waynesboro Home Near Wintergreen Charlottesville
2.0 star property
Waynesboro
The price is 6.349.248 ₫
18.429.006 ₫ total
includes taxes & fees
12 Mar - 13 Mar
Waynesboro Home Near Wintergreen Charlottesville
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 3.199.328 ₫
8.906.719 ₫ total
includes taxes & fees
16 Mar - 17 Mar
Wintergreen Ski Resort Condo w/ Golf Access!
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 3.907.376 ₫
5.949.701 ₫ total
includes taxes & fees
12 Mar - 13 Mar
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)
"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 2.333.936 ₫
4.669.970 ₫ total
includes taxes & fees
12 Mar - 13 Mar
The Urban Cowboy
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 2.333.936 ₫
4.669.970 ₫ total
includes taxes & fees
12 Mar - 13 Mar
The Shenandoah Suite
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 3.810.165 ₫
9.534.347 ₫ total
includes taxes & fees
12 Mar - 13 Mar
Blackwood Chalet
Apartment, Private Bathroom (Secret Garden Studio) | Interior

Secret Garden Studio

Secret Garden Studio
2.0 star property
Staunton
9.4 out of 10, Exceptional, (3 reviews)
"Great studio, more spacious than I expected. Great thought put into design and decor! Hosts were very responsive and I would definitely rent again!"
United States
Kathleen
Secret Garden Studio
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 2.333.936 ₫
4.669.970 ₫ total
includes taxes & fees
24 Mar - 25 Mar
The Bohemian Suite
Apartment, Private Bathroom (The Serendipity Suite) | Exterior

The Serendipity Suite

The Serendipity Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (6 reviews)
"Everything from start to finish was great"
United States
Heidi
The price is 2.333.936 ₫
4.669.970 ₫ total
includes taxes & fees
17 Mar - 18 Mar
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)
"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 2.333.936 ₫
4.669.970 ₫ total
includes taxes & fees
24 Mar - 25 Mar
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

Motel 6 Staunton, VA

Motel 6 Staunton, VA

10/10 Excellent
"Clean AC filters. Thank You"
paul j 1-night trip
Posted 3 hours ago
Motel 6 Staunton, 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 Shenandoah National Park. 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.