Greenwood Holiday Rentals

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Greenwood holiday rentals

Exterior

Unique Cypress cottage, close to Charlottesville with mountain views.

Unique Cypress cottage, close to Charlottesville with mountain views.
Charlottesville
10.0 out of 10, Exceptional, (49 reviews)
"Comfy rooms, great layout, pretty scenery, exceeded expectations "
United States
Molly P.
The price is HK$1,175
HK$2,257 total
includes taxes & fees
25 Mar - 26 Mar
Unique Cypress cottage, close to Charlottesville with mountain views.
Exterior

Brand new serene luxury cottage just off the Brew Ridge Trail

Brand new serene luxury cottage just off the Brew Ridge Trail
Afton
10.0 out of 10, Exceptional, (5 reviews)
"The property was very clean and awesome! It met the needs of our 2 day stay with our pets. We would stay again!"
United States
Joni K.
The price is HK$499
HK$1,133 total
includes taxes & fees
30 Mar - 31 Mar
Brand new serene luxury cottage just off the Brew Ridge Trail
Property grounds

The Cottage @ Afton Mountain- Close to Wineries!

The Cottage @ Afton Mountain- Close to Wineries!
Afton
10.0 out of 10, Exceptional, (22 reviews)
"Very clean and central to the wineries."
United States
Cynda
The price is HK$1,135
HK$2,489 total
includes taxes & fees
29 Mar - 30 Mar
The Cottage @ Afton Mountain- Close to Wineries!
Exterior

Unit 5 - Cozy Lower Level Studio Suite

Unit 5 - Cozy Lower Level Studio Suite
Charlottesville
10.0 out of 10, Exceptional, (30 reviews)
"The location was great and the place was very nice. "
United States
Amanda L.
The price is HK$848
HK$1,149 total
includes taxes & fees
25 Mar - 26 Mar
Unit 5 - Cozy Lower Level Studio Suite
Smart TV

RATED A TOP RIVER CABIN In Virginia. Stunning views! The heart of Nelson County.

RATED A TOP RIVER CABIN In Virginia. Stunning views! The heart of Nelson County.
Faber
10.0 out of 10, Exceptional, (53 reviews)
"Great cabin, very peaceful. John communicated everything perfectly. One of the best places we have stayed"
United States
Timothy D.
The price is HK$1,192
HK$1,514 total
includes taxes & fees
25 Mar - 26 Mar
RATED A TOP RIVER CABIN In Virginia. Stunning views! The heart of Nelson County.
Exterior

Unit 3 - Luxury King Suite with Private Balcony

Unit 3 - Luxury King Suite with Private Balcony
Charlottesville
10.0 out of 10, Exceptional, (22 reviews)
"Very nice space. Clean, quiet, and comfortable. Host very responsive to any questions or information needs. Would definitely consider staying here again."
United States
Brian T.
The price is HK$1,339
HK$1,746 total
includes taxes & fees
30 Mar - 31 Mar
Unit 3 - Luxury King Suite with Private Balcony
Property grounds

The Firefly Springhouse

The Firefly Springhouse
Staunton
9.8 out of 10, Exceptional, (51 reviews)
"The space was great for a getaway, highly recommended."
United States
Matt E.
The price is HK$649
HK$896 total
includes taxes & fees
25 Mar - 26 Mar
The Firefly Springhouse
Exterior

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (104 reviews)
"Great stay with a fabulous view! Very cozy and comfortable! We had a wonderful little getaway!"
United States
Vicki E.
The price is HK$846
HK$1,918 total
includes taxes & fees
25 Mar - 26 Mar
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Terrace/patio

Afton Cottage w/ Hot Tub, Firepit, Mountain Views

Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Afton
10.0 out of 10, Exceptional, (12 reviews)
"Very tranquil place. "
United States
Thomas K.
The price is HK$1,073
HK$2,490 total
includes taxes & fees
25 Mar - 26 Mar
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Exterior detail

Stay in Crozet Train Suite in Downtown Crozet

Stay in Crozet Train Suite in Downtown Crozet
Crozet
10.0 out of 10, Exceptional, (69 reviews)
"Perfect location for multiple restaurants & some shopping.Very clean...enjoyable stay."
United States
Roberta F.
The price is HK$1,175
HK$1,905 total
includes taxes & fees
25 Mar - 26 Mar
Stay in Crozet Train Suite in Downtown Crozet
Property grounds

Cozy cabin for 2 w/ great mt views & walking trails!

Cozy cabin for 2 w/ great mt views & walking trails!
Schuyler
10.0 out of 10, Exceptional, (178 reviews)
"Everything was amazing "
United States
Richard
The price is HK$1,136
HK$1,539 total
includes taxes & fees
12 Apr - 13 Apr
Cozy cabin for 2 w/ great mt views & walking trails!
Property grounds

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Wintergreen Resort
10.0 out of 10, Exceptional, (13 reviews)
"Fantastic little studio located right at the slopes. Very clean and many thoughtful touches. Great stay. "
United States
Lloyd F.
The price is HK$635
HK$1,680 total
includes taxes & fees
25 Mar - 26 Mar
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Outdoor spa tub

NEW! Cheerful 2 bd bungalow with hot tub. Must see!

NEW! Cheerful 2 bd bungalow with hot tub. Must see!
Waynesboro
9.8 out of 10, Exceptional, (48 reviews)
"loved the quiet location, sunny private back yard, and well-stocked kitchen"
United States
George D.
NEW! Cheerful 2 bd bungalow with hot tub. Must see!
Exterior

Shenandoah Mansion

Shenandoah Mansion
Elkton
9.0 out of 10, Wonderful, (7 reviews)
"The house was amazing and very cozy. My family enjoyed the amenities that come with the property. I would visit again."
United States
Jansenia Diane
The price is HK$1,473
HK$9,431 total
includes taxes & fees
25 Mar - 26 Mar
Shenandoah Mansion
Property grounds

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland
9.6 out of 10, Exceptional, (149 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is HK$862
HK$1,891 total
includes taxes & fees
30 Mar - 31 Mar
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Property grounds

Endless Mountain Top Views from All The Way Up!

Endless Mountain Top Views from All The Way Up!
Wintergreen Resort
10.0 out of 10, Exceptional, (99 reviews)
"Highly recommend staying at this beautiful condo! The kitchen has everything you need, the views are breath-taking, the condo is very clean, and the hosts are very communicative and helpful. Will definitely stay here again the next time we travel to the area!"
United States
Allison N.
The price is HK$838
HK$2,146 total
includes taxes & fees
26 Mar - 27 Mar
Endless Mountain Top Views from All The Way Up!
Smart TV, DVD player, books, music library

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Roseland
10.0 out of 10, Exceptional, (96 reviews)
"Great spot for a stay, hostess was amazing, highly recommend!!"
United States
Charles R.
The price is HK$1,018
HK$1,539 total
includes taxes & fees
26 Mar - 27 Mar
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Dining

The Pop Inn: Family Destination, Walk Dwntwn

The Pop Inn: Family Destination, Walk Dwntwn
Staunton
10.0 out of 10, Exceptional, (22 reviews)
"Great place- very clean & convenient"
United States
Susan B.
The price is HK$776
HK$1,746 total
includes taxes & fees
29 Mar - 30 Mar
The Pop Inn: Family Destination, Walk Dwntwn
Interior

High Street | Walk to Everything Crozet | Pet-Friendly

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (106 reviews)
"Such a lovely cottage in a great spot!We enjoyed Crozet and time at Praha bakery, Star Hill Brewery, King Family Vineyard, and Mint Springs Park!"
United States
Polly H.
The price is HK$1,567
HK$2,609 total
includes taxes & fees
25 Mar - 26 Mar
High Street | Walk to Everything Crozet | Pet-Friendly
Terrace/patio

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (16 reviews)
"Very quiet and peaceful stay. "
United States
Timika
The price is HK$973
HK$1,563 total
includes taxes & fees
25 Mar - 26 Mar
Love Ridge Mountain Lodging
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

6/10 Okay
"The grab and go breakfast is essentially some protein bars and some old muffins in bags. Really the worst I have seen. Why would you state breakfast is included when there is really not much to offer. "
Kamran 1-night trip
Posted 11 hours ago
Extended Stay America Premier Suites - 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:

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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.

What are some of the best holiday rentals that Greenwood has to offer?

4 BR cabin mins to trails & breweries pets welcome: This holiday home rental outside of Greenwood offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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 Virginia Discovery Museum, 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.