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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sep - 6 Sep
In four months
2 Oct - 4 Oct

Our top choices for Greenwood holiday rentals

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
9.2 out of 10, Wonderful, (61 reviews)
"Very good value, would definitely stay again"
United States
Frank
The price is 2.079.991 ₫
2.315.109 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Affordable Suites of America Waynesboro
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 2.343.281 ₫
4.688.668 ₫ total
includes taxes & fees
10 Jun - 11 Jun
The Urban Cowboy
Street view

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (242 reviews)
"Stay here 2 times a year, and doesn’t disappoint."
United States
Kate
The price is 3.001.506 ₫
3.340.676 ₫ total
includes taxes & fees
21 Jun - 22 Jun
Valley Extended Suites
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
10.0 out of 10, Exceptional, (1 review)
"Our stay was perfect. Hotels.com really messed up the booking and I almost didn’t have a place to stay. The host at this property held the room for me and we handled everything directly. He was great, the room was spectacular!"
United States
Crystal
The price is 3.009.405 ₫
3.439.621 ₫ total
includes taxes & fees
10 Jun - 11 Jun
SONSAK - MONTICELLO
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 2.343.281 ₫
4.688.668 ₫ total
includes taxes & fees
10 Jun - 11 Jun
The Serendipity 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 3.212.138 ₫
8.942.382 ₫ total
includes taxes & fees
17 Jun - 18 Jun
Wintergreen Ski Resort Condo w/ Golf Access!
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

Sleep Inn Staunton

Sleep Inn Staunton

10/10 Excellent
"The room was very nice and clean. The property was quiet, parking convenient, dog friendly. We didn’t stay for the breakfast but were happy with the convenience of the location, and the peaceful time there."
Jillianna 1-night trip
Posted 4 hours ago
Sleep Inn Staunton

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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.