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Check prices for these dates

Tonight
10 Dec - 11 Dec
Tomorrow
11 Dec - 12 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Our top choices for Greenwood holiday rentals

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

Apartment in Fishersville

Valley Extended Suites
3.0 star property
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 3.005.268 ₫
3.344.863 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Valley Extended Suites
Cabin, Private Bathroom (Blackwood Chalet) | Exterior
Blackwood Chalet

Cabin in Nellysford

Blackwood Chalet
2.0 star property
10.0 out of 10, Exceptional, (3)
"Love the area"
United States
Toni
The price is 4.456.530 ₫
10.278.762 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Blackwood Chalet
Hanging Rock Cabin, 2 Bedrooms, Jetted Tub, Mountain View | Terrace/patio
Love Ridge Mountain Lodging

Cabin in Montebello

Love Ridge Mountain Lodging
3.0 star property
10.0 out of 10, Exceptional, (13)
"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
16 Dec - 17 Dec
Love Ridge Mountain Lodging
Interior detail
Afton Mountain Vineyards

Cabin in Afton

Afton Mountain Vineyards
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
11 Dec - 12 Dec
Afton Mountain Vineyards
Standard Suite, 1 Queen Bed | Living area | LCD TV, DVD player
Affordable Suites of America Waynesboro

Apartment in Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
9.4 out of 10, Exceptional, (53)
"Always a pleasant stay."
United States
MARJORIE
The price is 2.188.710 ₫
2.436.035 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
Affordable Suites of America Waynesboro
Terrace/patio
Affordable Suites Charlottesville

Apartment in Fry's Spring

Affordable Suites Charlottesville
2.0 star property
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
House (3 Bedrooms) | Interior
Modern Nellysford Getaway on 40 Private Acres!

Cottage in Nellysford

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
The price is 6.460.650 ₫
16.040.344 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Modern Nellysford Getaway on 40 Private Acres!
Apartment | 4 bedrooms
Stoney Creek Cottage Wintergreen w EV Charger

Apartment in Nellysford

Stoney Creek Cottage Wintergreen w EV Charger
2.0 star property
The price is 13.778.032 ₫
24.766.745 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Stoney Creek Cottage Wintergreen w EV Charger
Luxury Room, Ensuite (The Storefront) | Bar (on property)
The Storefront

Townhouse in Staunton

The Storefront
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
14 Dec - 15 Dec
The Storefront
Apartment, Private Bathroom (The Urban Cowboy) | Exterior
The Urban Cowboy

Apartment in Staunton

The Urban Cowboy
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 2.346.930 ₫
4.210.762 ₫ total
includes taxes & fees
11 Dec - 12 Dec
The Urban Cowboy
Apartment, Private Bathroom (The Bohemian Suite) | Lobby
The Bohemian Suite

Apartment in Staunton

The Bohemian Suite
2.0 star property
10.0 out of 10, Exceptional, (6)
"It was really nice. A bit pricey. "
United States
Bonny
The price is 2.346.930 ₫
4.210.762 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
The Bohemian Suite
Apartment, Private Bathroom (The Serendipity Suite) | Exterior
The Serendipity Suite

Apartment in Staunton

The Serendipity Suite
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 2.346.930 ₫
4.210.762 ₫ total
includes taxes & fees
11 Dec - 12 Dec
The Serendipity Suite
Apartment, Private Bathroom (North Central Loft) | Exterior
North Central Loft

Apartment in Staunton

North Central Loft
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 4.746.600 ₫
9.930.942 ₫ total
includes taxes & fees
16 Dec - 17 Dec
North Central Loft
Apartment, Private Bathroom (The Bons Amis Suite) | Lounge
The Bons Amis Suite

Apartment in Staunton

The Bons Amis Suite
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 2.346.930 ₫
4.210.762 ₫ total
includes taxes & fees
15 Dec - 16 Dec
The Bons Amis Suite
Apartment, Private Bathroom (The Shenandoah Suite) | Exterior
The Shenandoah Suite

Apartment in Staunton

The Shenandoah Suite
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 2.346.930 ₫
4.210.762 ₫ total
includes taxes & fees
11 Dec - 12 Dec
The Shenandoah 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

Extended Stay America Premier Suites - Charlottesville

Extended Stay America Premier Suites - Charlottesville

10/10 Excellent
"The room was spotless!"
James 1-night trip
Posted 3 days ago
Extended Stay America Premier Suites - 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 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.