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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Top Holiday Rentals in Greenwood

Studio Suite | Private kitchen | Full-sized fridge, microwave, oven, stovetop
Valley Extended Suites

Apartment in Fishersville

3.0 star property
9.0 out of 10, Wonderful, (212)
"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 3.005.268 ₫
3.344.863 ₫ total
includes taxes & fees
25 Nov - 26 Nov
Valley Extended Suites
Apartment, Private Bathroom (The Shenandoah Suite) | Exterior
The Shenandoah Suite

Apartment in Staunton

2.0 star property
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 2.346.218 ₫
4.209.484 ₫ total
includes taxes & fees
25 Nov - 26 Nov
The Shenandoah Suite
Hanging Rock Cabin, 2 Bedrooms, Jetted Tub, Mountain View | Terrace/patio
Love Ridge Mountain Lodging

Cabin in Montebello

3.0 star property
10.0 out of 10, Exceptional, (12)
"Amazing stay I had, very peaceful and very quiet. "
United States
Abby
The price is 4.735.551 ₫
6.899.744 ₫ total
includes taxes & fees
25 Nov - 26 Nov
Love Ridge Mountain Lodging
House (3 Bedrooms) | Interior
Modern Nellysford Getaway on 40 Private Acres!

Cottage in Nellysford

3.0 star property
The price is 7.117.740 ₫
15.172.649 ₫ total
includes taxes & fees
25 Nov - 26 Nov
Modern Nellysford Getaway on 40 Private Acres!
House | 4 bedrooms
Waynesboro Home Near Wintergreen Charlottesville

Holiday Home in Waynesboro

2.0 star property
Waynesboro Home Near Wintergreen Charlottesville
Interior detail
Afton Mountain Vineyards

Cabin in Afton

2.5 star property
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 9.226.700 ₫
10.361.584 ₫ total
includes taxes & fees
25 Nov - 26 Nov
Afton Mountain Vineyards
Luxury Room, Ensuite (The Storefront) | Bar (on property)
The Storefront

Townhouse in Staunton

3.5 star property
8.8 out of 10, Excellent, (58)
"Great place to stay in charming Staunton!"
United States
Kate
The price is 3.927.938 ₫
5.981.011 ₫ total
includes taxes & fees
25 Nov - 26 Nov
The Storefront
Apartment, Private Bathroom (The Urban Cowboy) | Exterior
The Urban Cowboy

Apartment in Staunton

2.0 star property
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 price is 2.346.218 ₫
4.209.484 ₫ total
includes taxes & fees
8 Dec - 9 Dec
The Urban Cowboy
Apartment, Private Bathroom (The Bohemian Suite) | Lobby
The Bohemian Suite

Apartment in Staunton

2.0 star property
10.0 out of 10, Exceptional, (6)
"It was really nice. A bit pricey. "
United States
Bonny
The price is 2.346.218 ₫
4.209.484 ₫ total
includes taxes & fees
8 Dec - 9 Dec
The Bohemian Suite
Apartment | 4 bedrooms
Stoney Creek Cottage Wintergreen w EV Charger

Apartment in Nellysford

2.0 star property
The price is 5.843.538 ₫
14.093.716 ₫ total
includes taxes & fees
25 Nov - 26 Nov
Stoney Creek Cottage Wintergreen w EV Charger
Cabin, Private Bathroom (Blackwood Chalet) | Exterior
Blackwood Chalet

Cabin in Nellysford

2.0 star property
10.0 out of 10, Exceptional, (3)
"Love the area"
United States
Toni
The price is 4.455.178 ₫
10.275.644 ₫ total
includes taxes & fees
30 Nov - 1 Dec
Blackwood Chalet
Apartment, Private Bathroom (North Central Loft) | Exterior
North Central Loft

Apartment in Staunton

2.0 star property
10.0 out of 10, Exceptional, (3)
"Clean, comfortable, fun, well appointed and thoughtful details. A great place. "
United States
Stacey
The price is 4.745.160 ₫
9.927.929 ₫ total
includes taxes & fees
30 Nov - 1 Dec
North Central Loft
Apartment, Private Bathroom (The Serendipity Suite) | Exterior
The Serendipity Suite

Apartment in Staunton

2.0 star property
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 2.346.218 ₫
4.209.484 ₫ total
includes taxes & fees
8 Dec - 9 Dec
The Serendipity Suite
Apartment, Private Bathroom (The Bons Amis Suite) | Lounge
The Bons Amis Suite

Apartment in Staunton

2.0 star property
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 2.346.218 ₫
4.209.484 ₫ total
includes taxes & fees
8 Dec - 9 Dec
The Bons Amis Suite
House | 5 bedrooms, Internet
Time to Wine Down - Family Home

Holiday Home in Afton

2.0 star property
Time to Wine Down - Family Home
House | 3 bedrooms, Internet
Wintergreen Ridge Retreat - Family Home

Holiday Home in Pedlars Edge

2.0 star property
Wintergreen Ridge Retreat - Family Home
House | 4 bedrooms, Internet
Adventure Awaits - Family Home

Holiday Home in Laurel Ridge

2.0 star property
Adventure Awaits - Family Home
Suite | 3 bedrooms, Internet
Waterfall Hikes Hike Bike Fish Ski Resort

Apartment in Nellysford

2.0 star property
Waterfall Hikes Hike Bike Fish Ski Resort
House | 5 bedrooms, Internet
Love Afton Cabin - Family Home

Holiday Home in Afton

2.0 star property
Love Afton Cabin - Family Home
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

Quality Inn Verona - Staunton North

Quality Inn Verona - Staunton North

10/10 Excellent
"Clean room, great check in staff, very friendly! "
Karyna 1-night trip
Posted 2 days ago
Quality Inn Verona - Staunton North

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.