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Check prices for these dates

Tonight
15 Jan - 16 Jan
Tomorrow
16 Jan - 17 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

Our top choices for Greenwood holiday rentals

Street view

Apartment in Fishersville

Valley Extended Suites
3.0 star property
9.0 out of 10, Wonderful, (217 reviews)
"Nice stay"
United States
swati
The price is ฿3,589
฿3,995 total
includes taxes & fees
19 Jan - 20 Jan
Valley Extended Suites
Cabin, Private Bathroom (Blackwood Chalet) | Lounge

Cabin in Nellysford

Blackwood Chalet
2.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"Love the area"
United States
Toni
The price is ฿7,713
฿14,958 total
includes taxes & fees
20 Jan - 21 Jan
Blackwood Chalet
Ravens Roost, 3 Bedrooms, Hot Tub, Mountain View | Terrace/patio

Cabin in Lyndhurst

Love Ridge Mountain Lodging
3.0 star property
10.0 out of 10, Exceptional, (15 reviews)
"Amazing stay I had, very peaceful and very quiet. "
United States
Abby
The price is ฿3,911
฿6,281 total
includes taxes & fees
19 Jan - 20 Jan
Love Ridge Mountain Lodging
Interior detail

Cabin in Afton

Afton Mountain Vineyards
2.5 star property
10.0 out of 10, Exceptional, (1 review)
"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 ฿11,019
฿12,374 total
includes taxes & fees
19 Jan - 20 Jan
Afton Mountain Vineyards
Standard Suite, 1 Queen Bed | Private kitchen | Full-sized fridge, microwave, oven, stovetop

Apartment in Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
9.4 out of 10, Exceptional, (53 reviews)
"Always a pleasant stay."
United States
MARJORIE
Affordable Suites of America Waynesboro
Apartment | 4 bedrooms

Apartment in Nellysford

Stoney Creek Cottage Wintergreen w EV Charger
2.0 star property
Stoney Creek Cottage Wintergreen w EV Charger
Luxury Room, Ensuite (The Storefront) | Lounge

Townhouse in Staunton

The Storefront
3.5 star property
8.8 out of 10, Excellent, (58 reviews)
"Great place to stay in charming Staunton!"
United States
Kate
The price is ฿4,691
฿7,143 total
includes taxes & fees
19 Jan - 20 Jan
The Storefront
Apartment, Private Bathroom (The Urban Cowboy) | Exterior

Apartment in Staunton

The Urban Cowboy
2.0 star property
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 ฿2,802
฿5,254 total
includes taxes & fees
19 Jan - 20 Jan
The Urban Cowboy
Private kitchen

Apartment in Fishersville

Fishersville Oasis
2.0 star property
The price is ฿3,117
฿6,097 total
includes taxes & fees
19 Jan - 20 Jan
Fishersville Oasis
Apartment, Private Bathroom (North Central Loft) | Bathroom

Apartment in Staunton

North Central Loft
2.0 star property
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 ฿5,667
฿11,856 total
includes taxes & fees
28 Jan - 29 Jan
North Central Loft
Apartment, Private Bathroom (The Bohemian Suite) | Lobby

Apartment in Staunton

The Bohemian Suite
2.0 star property
10.0 out of 10, Exceptional, (6 reviews)
"It was really nice. A bit pricey. "
United States
Bonny
The price is ฿2,802
฿5,254 total
includes taxes & fees
19 Jan - 20 Jan
The Bohemian Suite
Apartment, Private Bathroom (The Bons Amis Suite) | Exterior

Apartment in Staunton

The Bons Amis Suite
2.0 star property
9.4 out of 10, Exceptional, (3 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 ฿2,802
฿5,254 total
includes taxes & fees
19 Jan - 20 Jan
The Bons Amis Suite
House | 4 bedrooms

Holiday Home in Waynesboro

Waynesboro Home Near Wintergreen Charlottesville
2.0 star property
The price is ฿7,945
฿22,017 total
includes taxes & fees
18 Jan - 19 Jan
Waynesboro Home Near Wintergreen Charlottesville
Apartment, Private Bathroom (The Shenandoah Suite) | Exterior

Apartment in Staunton

The Shenandoah Suite
2.0 star property
10.0 out of 10, Exceptional, (5 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 ฿2,802
฿5,254 total
includes taxes & fees
19 Jan - 20 Jan
The Shenandoah Suite
Apartment, Private Bathroom (The Serendipity Suite) | Exterior

Apartment in Staunton

The Serendipity Suite
2.0 star property
10.0 out of 10, Exceptional, (6 reviews)
"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 ฿2,802
฿5,254 total
includes taxes & fees
19 Jan - 20 Jan
The Serendipity 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

English Inn of Charlottesville

English Inn of Charlottesville

10/10 Excellent
"Breakfast staff rocks!"
Carlos 1-night trip
Posted 2 days ago
English Inn of Charlottesville

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 War Fields, 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.