Photo by Karyn Leary

Greenwood Holiday Rentals

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Check prices for these dates

Tonight
16 Dec - 17 Dec
Tomorrow
17 Dec - 18 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Greenwood holiday rentals

Street view
Valley Extended Suites

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (216)
"I liked the cleanliness of the suite, the fully staffed kitchen, the large bathroom, the comfortable bed, the ease and safety of the parking area."
United States
Tammy
The price is S$164
includes taxes & fees
22 Dec - 23 Dec
Valley Extended Suites
Lobby
The Bohemian Suite

The Bohemian Suite

The Bohemian Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (6)
"It was really nice. A bit pricey. "
United States
Bonny
The price is S$206
includes taxes & fees
5 Jan - 6 Jan, 2026
The Bohemian Suite
Terrace/patio
Love Ridge Mountain Lodging

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Montebello
10.0 out of 10, Exceptional, (13)
"Amazing stay I had, very peaceful and very quiet. "
United States
Abby
The price is S$338
includes taxes & fees
17 Dec - 18 Dec
Love Ridge Mountain Lodging
Private kitchen
Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.4 out of 10, Exceptional, (53)
"Always a pleasant stay."
United States
MARJORIE
The price is S$119
includes taxes & fees
6 Jan - 7 Jan, 2026
Affordable Suites of America Waynesboro
Living area
Affordable Suites Charlottesville

Affordable Suites Charlottesville

Affordable Suites Charlottesville
2.0 star property
Fry's Spring
8.0 out of 10, Very good, (80)
"Simple, clean comfortable suite. Full kitchen with frig, stove and microwave. Convenient to UVA campus and football stadium. "
United States
Anonymous traveller
Affordable Suites Charlottesville
Interior detail
Afton Mountain Vineyards

Afton Mountain Vineyards

Afton Mountain Vineyards
2.5 star property
Afton
10.0 out of 10, Exceptional, (1)
"Amazing little cottage with everything you need. Loved the back porch and listening to music from the winery and enjoying the view. Good news, did not hear the music inside. "
United States
Kristin
The price is S$507
includes taxes & fees
22 Dec - 23 Dec
Afton Mountain Vineyards
4 bedrooms
Stoney Creek Cottage Wintergreen w EV Charger

Stoney Creek Cottage Wintergreen w EV Charger

Stoney Creek Cottage Wintergreen w EV Charger
2.0 star property
Nellysford
The price is S$540
includes taxes & fees
17 Dec - 18 Dec
Stoney Creek Cottage Wintergreen w EV Charger
Interior
Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is S$953
includes taxes & fees
2 Jan - 3 Jan, 2026
Modern Nellysford Getaway on 40 Private Acres!
Exterior
The Serendipity Suite

The Serendipity Suite

The Serendipity Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (6)
"Cute and tidy. Easy check in and out. Easy parking and walk to dining. EV charge is for teslas, you'll need an adapter."
United States
Jennifer
The price is S$206
includes taxes & fees
17 Dec - 18 Dec
The Serendipity Suite
Exterior
The Urban Cowboy

The Urban Cowboy

The Urban Cowboy
2.0 star property
Staunton
8.6 out of 10, Excellent, (7)
"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 Urban Cowboy
Lounge
Blackwood Chalet

Blackwood Chalet

Blackwood Chalet
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (3)
"Love the area"
United States
Toni
The price is S$726
includes taxes & fees
22 Dec - 23 Dec
Blackwood Chalet
Lounge
The Storefront

The Storefront

The Storefront
3.5 star property
Staunton
8.8 out of 10, Excellent, (58)
"Great place to stay in charming Staunton!"
United States
Kate
The price is S$293
includes taxes & fees
14 Jan - 15 Jan, 2026
The Storefront
Exterior
The Shenandoah Suite

The Shenandoah Suite

The Shenandoah Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (5)
"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 S$206
includes taxes & fees
18 Dec - 19 Dec
The Shenandoah Suite
Bathroom
North Central Loft

North Central Loft

North Central Loft
2.0 star property
Staunton
10.0 out of 10, Exceptional, (3)
"Clean, comfortable, fun, well appointed and thoughtful details. A great place. "
United States
Stacey
The price is S$486
includes taxes & fees
4 Jan - 5 Jan, 2026
North Central Loft
Exterior
The Bons Amis Suite

The Bons Amis Suite

The Bons Amis Suite
2.0 star property
Staunton
9.4 out of 10, Exceptional, (3)
"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 S$206
includes taxes & fees
5 Jan - 6 Jan, 2026
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

Hampton Inn Charlottesville

Hampton Inn Charlottesville

10/10 Excellent
"Im not a breakfast person, but I was there dsuly during my stay. The staff was courteous and the maintenance man seemed to live there, he worked 24 hours. Everytime I come here I stay here."
Aliya 2-night trip
Posted 1 day ago
Hampton Inn Charlottesville

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 War Fields, 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.