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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 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 ฿4,092
฿4,677 total
includes taxes & fees
10 May - 11 May
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, (55 reviews)
"Friendly staff "
United States
Kyle
The price is ฿2,546
฿2,833 total
includes taxes & fees
10 May - 11 May
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 ฿13,488
฿15,147 total
includes taxes & fees
11 May - 12 May
Afton Mountain Vineyards
Street view

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (231 reviews)
"Clean and had a kitchenette area with stove, fridge. Felt very safe."
United States
Kurt
The price is ฿3,673
฿4,088 total
includes taxes & fees
12 May - 13 May
Valley Extended Suites
Apartment, Private Bathroom (Valley Oasis) | Private kitchen

Fishersville Oasis

Fishersville Oasis
2.0 star property
Fishersville
The price is ฿3,706
฿6,814 total
includes taxes & fees
11 May - 12 May
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, (16 reviews)
"Very quiet and peaceful stay. "
United States
Timika
The price is ฿4,519
฿7,008 total
includes taxes & fees
11 May - 12 May
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 ฿7,959
฿19,760 total
includes taxes & fees
20 May - 21 May
Modern Nellysford Getaway on 40 Private Acres!
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 ฿6,335
฿13,462 total
includes taxes & fees
18 May - 19 May
North Central Loft
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 ฿4,801
฿7,311 total
includes taxes & fees
17 May - 18 May
The Storefront
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 ฿5,156
฿12,234 total
includes taxes & fees
11 May - 12 May
Blackwood Chalet
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 ฿2,924
฿5,821 total
includes taxes & fees
2 Jun - 3 Jun
The Serendipity Suite
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 ฿2,989
฿5,894 total
includes taxes & fees
11 May - 12 May
The Urban Cowboy
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 ฿3,931
฿10,944 total
includes taxes & fees
11 May - 12 May
Wintergreen Ski Resort Condo w/ Golf Access!
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 ฿3,021
฿5,930 total
includes taxes & fees
26 May - 27 May
The Bohemian 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, (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 ฿2,891
฿5,785 total
includes taxes & fees
26 May - 27 May
The Shenandoah 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 ฿2,891
฿5,785 total
includes taxes & fees
2 Jun - 3 Jun
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

Holiday Inn Express & Suites Charlottesville by IHG

Holiday Inn Express & Suites Charlottesville by IHG

8/10 Good
"Was surprised being told there was a $5 parking lot fee per car per night. 2 cars 2 nights $20 plus tax. Breakfast good and clean room"
John 2-night trip
Posted 5 hours ago
Holiday Inn Express & Suites Charlottesville by IHG

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 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.