Greenwood Holiday Rentals

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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Greenwood holiday rentals

Terrace/patio

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (16 reviews)
"Amazing stay I had, very peaceful and very quiet. "
United States
Abby
The price is HK$971
HK$1,559 total
includes taxes & fees
4 Feb - 5 Feb
Love Ridge Mountain Lodging
Street view

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (217 reviews)
"Clean room great location quiet area"
United States
Krista
The price is HK$811
HK$903 total
includes taxes & fees
15 Feb - 16 Feb
Valley Extended Suites
Interior

High Street | Walk to Everything Crozet | Pet-Friendly

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (105 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$1,563
HK$2,602 total
includes taxes & fees
4 Feb - 5 Feb
High Street | Walk to Everything Crozet | Pet-Friendly
Games room

Shenandoah Mansion

Shenandoah Mansion
Elkton
10.0 out of 10, Exceptional, (6 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$875
HK$6,818 total
includes taxes & fees
2 Feb - 3 Feb
Shenandoah Mansion
Lounge

The Storefront

The Storefront
3.5 star property
Staunton
8.8 out of 10, Excellent, (58 reviews)
"Great place to stay in charming Staunton!"
United States
Kate
The price is HK$1,164
HK$1,773 total
includes taxes & fees
2 Feb - 3 Feb
The Storefront
Terrace/patio

Pine Cottage: Hot Tub, 2 mins to Bold Rock!

Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Nellysford
10.0 out of 10, Exceptional, (24 reviews)
"The house was so nice and clean and the host was great also and we had a great stay and would highly recommend it. "
United States
Jody W.
The price is HK$1,477
HK$3,633 total
includes taxes & fees
2 Feb - 3 Feb
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
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, (47 reviews)
"Great cottage. Very comfortable and good location."
United States
Paul W.
The price is HK$1,149
HK$2,215 total
includes taxes & fees
2 Feb - 3 Feb
Unique Cypress cottage, close to Charlottesville with mountain views.
Property grounds

Hillside Haven: Modern Retreat, Mountain Views

Hillside Haven: Modern Retreat, Mountain Views
Faber
10.0 out of 10, Exceptional, (32 reviews)
"Fantastic property with all the amenities near UVA, and lots of wineries."
United States
roberto c.
The price is HK$1,399
HK$3,256 total
includes taxes & fees
2 Feb - 3 Feb
Hillside Haven: Modern Retreat, Mountain Views
Exterior detail

Bee Mountain Cabin fireplace, kitchen, jacuzzi

Bee Mountain Cabin fireplace, kitchen, jacuzzi
Lyndhurst
10.0 out of 10, Exceptional, (11 reviews)
"The cabin is lovely and the scenery is beautiful."
United States
Kimmy M.
The price is HK$1,446
HK$1,852 total
includes taxes & fees
2 Feb - 3 Feb
Bee Mountain Cabin fireplace, kitchen, jacuzzi
Property grounds

The Cottage @ Afton Mountain- Close to Wineries!

The Cottage @ Afton Mountain- Close to Wineries!
Afton
9.8 out of 10, Exceptional, (20 reviews)
"Great place"
United States
Beverly
The price is HK$1,118
HK$2,475 total
includes taxes & fees
2 Feb - 3 Feb
The Cottage @ Afton Mountain- Close to Wineries!
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, (68 reviews)
"Perfect location for multiple restaurants & some shopping.Very clean...enjoyable stay."
United States
Roberta F.
The price is HK$1,172
HK$1,900 total
includes taxes & fees
2 Feb - 3 Feb
Stay in Crozet Train Suite in Downtown Crozet
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, (11 reviews)
"Very tranquil place. "
United States
Thomas K.
The price is HK$1,071
HK$2,519 total
includes taxes & fees
2 Feb - 3 Feb
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Fridge, microwave, oven, stovetop

Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy

Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Ivy
10.0 out of 10, Exceptional, (41 reviews)
"It was a lovely place to stay and the hosts were so kind. "
United States
Cooper C.
The price is HK$731
HK$1,461 total
includes taxes & fees
2 Feb - 3 Feb
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Exterior

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (4 reviews)
"We really enjoyed our stay here! Great location, and the condo was very clean and well stocked. Communication with the host was excellent as well. We look forward to returning back some day!"
United States
Alexander H.
The price is HK$742
HK$2,181 total
includes taxes & fees
2 Feb - 3 Feb
Laurelwood Hollow: Walk to Ski & Swim
Lounge

Blackwood Chalet

Blackwood Chalet
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (3 reviews)
"Love the area"
United States
Toni
The price is HK$1,360
HK$3,090 total
includes taxes & fees
3 Feb - 4 Feb
Blackwood Chalet
Property grounds

Welcome to the daughter of the stars

Welcome to the daughter of the stars
Mt Crawford
9.8 out of 10, Exceptional, (50 reviews)
"The place was absolutely perfect, inside and out. Location has amazing video.Look forward to the next stay!"
United States
Ed S.
The price is HK$492
HK$1,620 total
includes taxes & fees
3 Feb - 4 Feb
Welcome to the daughter of the stars
Exterior

Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi

Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi
Verona
10.0 out of 10, Exceptional, (59 reviews)
"Great place to stay. "
United States
Kelly H
The price is HK$1,102
HK$1,887 total
includes taxes & fees
22 Feb - 23 Feb
Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi
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, (90 reviews)
"Great spot for a stay, hostess was amazing, highly recommend!!"
United States
Charles R.
The price is HK$1,016
HK$1,536 total
includes taxes & fees
16 Feb - 17 Feb
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Outdoor dining

Escape to the Blue Ridge Mountains at Wine-tergreen!

Escape to the Blue Ridge Mountains at Wine-tergreen!
Wintergreen Resort
9.8 out of 10, Exceptional, (124 reviews)
"Everything was as is listed, we were off season so hiking and scenic views is what there was to do, relaxing. Host was accessible on phone, place was clean. "
United States
David L.
The price is HK$1,008
HK$2,141 total
includes taxes & fees
2 Mar - 3 Mar
Escape to the Blue Ridge Mountains at Wine-tergreen!
Outdoor spa tub

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

NEW! Cheerful 2 bd bungalow with hot tub. Must see!
Waynesboro
9.6 out of 10, Exceptional, (45 reviews)
"loved the quiet location, sunny private back yard, and well-stocked kitchen"
United States
George D.
The price is HK$914
HK$1,592 total
includes taxes & fees
2 Feb - 3 Feb
NEW! Cheerful 2 bd bungalow with hot tub. Must see!
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

Days Inn by Wyndham Waynesboro

Days Inn by Wyndham Waynesboro

10/10 Excellent
"Clean room,great staff . We had gotten a lot of ice and snow, they did a great job at having thier parking lot clear and safe to walk. "
Crystal 2-night trip
Posted 6 hours ago
Days Inn by Wyndham Waynesboro

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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  • 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.

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

Berry Hill Lake - Private Luxury Family Resort w/ Pool & Hot Tub - Pet Friendly: This holiday home rental outside of Greenwood is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.